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Learning To Listen

A provocative combination of truth-telling, hard-won life lessons, and powerful prose, An Ordinary Disaster is a concrete and hopeful demonstration that despite what may seem like our inability to hear it, and all of our attempts to avoid it, we can all learn to listen to ourselves, and to act upon the inner voice of our self, our sanity and our soul.

This raw, gritty, vulnerable memoir takes us from the author's vibrant—and emotionally vacant—youth in 1980’s San Francisco, through a deeply conflicted adulthood of depression, isolation, and addiction, all of which ran beneath successful careers in the early days of the internet and as a conference producer and entrepreneur. Starting, growing and eventually selling his own business while desperately trying to escape his inner darkness through sex, travel, and drinking, the author eventually rediscovers his love of the outdoors and his connection to physical movement and adventure, which leads to an awakening of his intuition, the end of his life-long love affair with alcohol, and the rediscovery of his identity as a man.

Interview with the Author

My friend Michael Lipson interviewed me recently about the development and writing of the book, which began with the clear feeling that “I'm here to tell the truth.” Writing “cemented my sense of self,” and “made me feel like another person.” “The creative act is a form of dreaming,” and in doing that dreaming, I came to feel a great weight lifted, and an expansion of self. Listen to the full interview here.

Introduction

When I sat down to write this book, all I knew was that I’m here to tell the truth—and that learning to do so had become so important that there was nothing else left to distract me from that task.

As I began, I felt that I wanted to tell the story of how I’d survived growing up in San Francisco in the 80’s, lived through years of depression and addiction, and eventually found my way back, healed myself, and become whole. I wanted to be transparent about how I suffered, how I endured, and how I made it out the other side.

Many of those stories did make their way into this book, but to find the truth that wanted to be told, I had to let them lead me into deeper territory. As I pulled the threads of memory and reconstructed the timeline of lost years, I kept finding more and more—or really, less and less—truth. I began to understand that it was the truth that had gone missing so early in my life, and that it was that absence that had pulled me down so far—and, also that had eventually brought me to the point of feeling compelled to dig it up myself.

The first part of the truth that wanted telling was the question that had tormented me for so long: “Who am I, and how could I not know?”

I did not know then how that tortuous, black and boiling emptiness was the natural response to the lack of the kind of straight, honest, direct talk that makes for real connection. Sure, there were other minor family traumas, and quite naturally I wanted to put as much distance between myself and both the silence and the chaos as possible. Going it alone, I felt mostly numb and hollow. I was desperate for something more, but unable to conceive of where that might come from.

My center was unformed, and I sought the usual substitutes that offer strong sensation, which left me even less conscious and often in pain. As I watched many of my friends self-destruct and even die, I congratulated myself for not having ‘an addictive personality’ simply because I had avoided annihilation—even so, I consumed almost everything, and certainly everyone, that I could lay my hands on.

All of this is common enough—and while it seems that struggle is part of what we all get to do here, the degree of depression, separation, loneliness, and groundlessness that I felt was tragic and unnecessary. Many of us make our way through much of our life doing all the things while not feeling all that much—and connecting with others even less. The result of what I describe as a lack of truth was a lack of real connection, to myself and to others.

It’s become widely accepted that the opposite of addiction is connection, which might seem to suggest that connection can be the cure. I think that’s true enough—and it’s just as true that the root cause of addiction in the first place is often a lack of connection so deeply felt as to amount to trauma—the natural response to which is, of course, to flee.

I became an expert in the art of leaving, which was convenient in that it also felt like freedom. It’s said that we get good at what we do, and also that we are what we do most often, and so my identity was constructed entirely of where I’d been, but was no longer, and where I was headed next. For those reasons and others, I was made up most of all of many things that I was not. I did my best to make sure that I wouldn’t be like my parents, or my sister, or jocks, or yuppies, or techies, or Burners, or the people who came to my conferences, or even like my friends. It wasn’t until much later in life that I began to consider the value in associating myself with anyone else at all, actually.

This not being so very many things drummed reverberating echoes of separation and loneliness into my young adulthood, and perpetrated an ever-deepening downward spiral of depression and ongoing, subtle addiction. Through much of my twenties and thirties, even as I succeeded in business and social life, I felt in constant danger of disappearing.

More than anything else, the persistent sense that there was something major missing from who I felt to be, and the simple fact that I was just so terribly unhappy, far too fucking often, finally gave me the message clearly enough that I really needed help. Old-fashioned talk therapy is agonizing—and agonizingly slow—but it did eventually teach me how to begin to be honest with myself. This kernel of truth-telling slowly grew, gradually becoming a burning desire for more truth in my own life, friendships, and relationships—and to develop a real relationship with the often quiet, always persistent voice of my ever-present unconscious.

Carl Jung called intuition “one of the most basic functions of the psyche,” and this deep voice is something so often absent in modern life, perhaps especially for men, that for many of us, lacking the guiding and protective whisper from within, it feels like we’re living under a bad star.

As I continued to dig within myself, this lack of a clear sense of what wants to be rising up from within, I came upon another truth that needed telling. I’d been running from my family, and then also from intoxication (even as I was intoxicating myself as a method of escape), but I’d also been avoiding what I saw as the limited and unappealing possibilities presented to me as a man.

Beginning as most men do with one perceived failure or another on the part of my father (through no real fault of his own), and also in the absence of close friendships with other men, I didn’t know what it was like to be in close and truthful connection with other men, and what little I did know of men mostly seemed uninspiring and unappealing. As much as I wanted to be recognized as one of them, I also did not want a normal nine-to-five, a daily commute, or a calendar full of nonsensical commitments, let alone a pile of mortgage debt, a boss—or an ex-wife. It was clear to me early on that many of our stories about men, at least the ones that I came to know, were not just old, tired, and obsolete, but also terribly constricted, expensive, and downright dangerous.

I always loved women, but as much as I sought love and connection with them, there was something missing so often that I couldn’t help but feel that it really was me that was failing, or incomplete, or incapable. It didn’t help that I was viscerally angry from not having even the first clue about how to achieve the deeper connection that I so desperately wanted—while at the same time being expected to pay for all of my relationships, from the first date onwards.

For much of my life, when asked, “do you love me?” most often, I simply did not know how to respond, because, down deep, I didn’t feel anything at all, and since we all get the message that we should love, and that we should intrinsically and intuitively know what love is, and how to love, and that we should want love, I began to think more and more that maybe I was a bad man—the kind of man who doesn’t really want love after all.

I was much better versed in no as opposed to “yes.” Many men are similarly accused, and it seems to me that, as bell hooks and many others explain so beautifully and honestly, our culture teaches men not to love, or that love is transactional, and keeps men away from real connection. I had resented love as something foreign and inaccessible, and it took a lot of practice in truth-telling to begin to feel something of what love might be, for myself.

Love had been an fantastical abstraction that I tried my damndest to pursue, but there was something that I could not learn about love from women. Reading deeper on the subjects of masculinity, patriarchy, feminism, love, and truth, it became clear to me that while men have played our own part in how our culture leaves us out of love, it’s something that we’ve all done together over the course of history, and that we’re all subject to—and also that the cultural system we’ve all inherited and still participate in continues to perpetuate many untruths about men and masculine identity. Not because of some conspiracy by, or for—or against—men, but because the stories that get told are the ones that get heard and repeated, and because we are taught to be silent in our masculinity, there are not enough stories of men and truth and love.

As I learned over time to listen more closely to myself, that voice began to melt my resentment and to reveal the beauty of the world that I’d been doing my best to escape for so long. My intuition spoke up to me more and more, soon becoming an active part of my daily life in a way that I could never previously have imagined.

Instead of struggling with a lack of purpose and endlessly agonizing over everyday decisions, I began to be able to focus my energy more and more in the direction of what felt good, and right, and interesting, and true. I found that I could form close relationships with other men, and that doing so healed a deep wound within me, and allowed me to finally feel love not just in my romantic relationships, but all around me, every day. I moved past whatever small and tarnished ideas I’d absorbed about men and masculinity to form my own more free and hopeful image of who I am, and also of what it can mean to be a man. I began to feel confident not just that I can do things, but that I am good.

I also became more and more convinced that, in many ways, we’ve built a world that is doing its best to destroy us, and that while that’s true, and it is a real challenge to live within that context, at the same time, there is now perhaps more than ever an opportunity to regain the lost connection to our selves—and to recast the archetypes of men.

My own rather ordinary disaster was born of personal and family history, and of my own actions, but also of the limiting and poisonous characterizations that we’ve propagated for far too long about men, and about each other. Whatever their origin, let me suggest that it does no good to continue to repeat stories that no longer serve us—and that, first of all, it our duty to show, by force of numbers and volume of voice, that we are not clinging to the past nor looking to others for direction, but that we are leading ourselves into the future, already, now, and moreso every day.

As Grayson Perry put it, “Men need to learn to equip themselves for peace”—and for connection—and not just with others, but with themselves. We need to learn tell new stories about ourselves—and to revisit the oldest ones and adapt them for the twenty-first century, and beyond. The way forward is not about erasing nor in remaking men, but in integrating our wild past, our troubled present, and our bright future to craft a forward-looking, colorful, cacophonous, diverse, living—and connected—vision of what and how we can be in the world.

All we need to do is to tell the truth.

Table of Contents

The full manuscript is currently about 66,000 words, or about 275 pages. I’ve serialized the entire work here in pre-publication form. You can of course read in sequence, but feel free to jump in anywhere!

⭐️⭐️ THANK YOU FOR READING ⭐️⭐️

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If you’re enjoying this work, please share this post with someone that loves memoir, and perhaps check out my post on 50+ Of My Favorite Memoirs, which also includes quite a few other writers right here on Substack!

Further reading

• The Descent of Man, Grayson Perry

• The Will To Change, bell hooks

• Lost Connections,

  Johann Hari

• The Man in Me, Ross Firestone (editor)

• The Myth Of Male Power, Warren Farrell

• The Flowering Wand: Rewilding the Sacred Masculine, Sophie Strand

Some questions for you

• Have you experienced depression, loneliness, or addiction? How have you gotten through those periods of your life?

• Do you have a clear sense of your own identity, beyond those things that you do most often?

• How much truth-telling goes on in your own relationships, on a regular basis?

• What have you learned from non-romantic relationships that has informed your romantic relationships?

• What are you here to do?

Share, comment, restack, recommend, and click the little ♡ heart right there
👇🏻 if you dig this piece. I’d love to hear from you!

I’m glad you’re here! And—this is a reader-supported publication. If you appreciate my work, please consider becoming a paying subscriber. As a full-time working writer, I appreciate every reader—and everyone who chooses to part with five bucks a month to support my writing. Almost all of my Substack remains free, but there are a few things that I make available only to paying subscribers, like my long-form handbook on intuition.

I needed to become another person.

I didn’t know what that might be like, or even how to find the path that could lead there—but I began to imagine that it was possible.

I had the feeling that I had to go towards something that should have felt like part of me, but just felt missing—the other half of my self: my unconscious. This is the part that knows without thinking, the part that speaks without hesitation, the part whose native language is pattern recognition, and the part from which springs what is most often known as “intuition.”

Since that seemed to be the key, I studied intuition and the unconscious, and practiced listening and taking action whenever I noticed them speaking up. With this practice over time, I began to hear the subtle, colorful, imaginative inner voice more and more—often in a way that reminded me of dreams—and of nature.

Simply put, I got better at intuition—but even as I did, another problem emerged. The problem with “intuition,” so to speak, is that despite my growing familiarity with what the word can refer to, I have the peculiar and persistent sense that it’s a word that doesn’t want to be used. The reason, I think, that the latent linguistic prejudice that intuition has carried still persists as something nebulous, mystical, or pseudo-scientific is because, even with a thousand ways to circle around it, intuition refuses to be named directly.

Intuition resists being pinned down precisely because it is a function of the unconscious. Just as the conscious is the realm of analysis, speech, and direct action, the unconscious is a world of whispers, symbols and hidden meanings. The unconscious does not have a voice of its own, and so when working with anything rooted there—the psychological shadow, dreams, intuition—we almost always have to move towards it indirectly.

The fact that we can’t just steer straight for this thing called intuition also serves to shelter it from the constant prodding of the alert, anxious, adult mind. We can only learn the language of intuition through the quiet craft of wayfinding in the inner—and outer—world. As our journeymaking reveals the paths as they emerge, and we find our way to fit ourselves into the seam of the wind, we absorb the raw material of the senses, and of sensing what makes sense.

Like intuition and dreams, full consciousness is a bodily function, and they all “express their contents in the language of nature.” What finally felt like freedom came from learning to listen to my unconscious, which is also the voice of the body, and of the natural world. They are all so closely connected as to be part of a greater whole.

I used to need a woman to hold me, and I used alcohol and whatever else I could lay my hands on, to provide relief from the feeling of not being held enough. I wrapped my soul in plastic, leaving me blind, breathless, and dumb.

It was only once I took up running—and sailing, and flying—that I began to feel change in a way that I hadn’t imagined was possible. That initial change led me to a series of major evolutions—changing my relationship with alcohol, making a concerted effort to develop deep relationships with other men, following my intuition at every possible turn, spending much more of time doing physical things in nature—and a daily writing practice.

There are any number of philosophies and spiritual systems that were helpful to me along the way: Jungian psychology, Stoicism, Daoism, Buddhism, psychedelic medicine, Taleb’s Antifragile, talk therapy, and adventure sports, just to name a few—and, the thing is, they all lead to the same place. Nature, connection, awareness, non-attachment, pattern recognition—and freedom.

The most fruitful of all of these for me has been Jung’s work, because of his focus on the “psychic depths” and the numinous connection between the individual, the unconscious, and the collective unconscious—which is also Self, Nature, and God. Jung’s work helped me make sense of the “impressive array of neuroses,” and “disorientation in everyday human situations” that I felt as a result of the “loss of instinct” which is “largely responsible for the pathological condition of contemporary culture.” It wasn’t just me—we are all suffering from a deep alienation and disconnection from nature and our unconscious selves.

As the effects of all of these changes combined and accumulated over time, at some point I began to feel transformed day by day, a newer man emerging each morning, not just free of a history that had once felt so bleak, but accelerating, my star drives burning hard away from an old, dark planet, on course for a new and brighter home.

Resurrection came crashing in, and in waves I was rocked and washed clean, bright and alive like never before. I’m back from the dead.

What had seemed to be the hard surface of the world has melted away to reveal a luminous web in which everything is connected, fed by a constant hum of intuitive input. Over time, these messages formed the foundation, and then the scaffolding, and then a complete philosophical architecture of my own—a guide for living well, at last—and it works, because I am!

This is nothing extraordinary—it’s how we’re all meant to live. It struck me recently that while it’s fairly well known at this point that “the opposite of addiction is connection,” I’ve never heard anyone describe the opposite of depression—perhaps because we tend to think it’s permanent.

We used to think that addiction was incurable too.

We should not accept addiction, depression, or even run-of-the-mill anxiety as any kind of normal human condition. Most often, these all-too-common soul afflictions are caused by curable errors in the way one is living. As opposed to things that we should accept and learn to manage, these are messages from the deeper psyche trying to tell us more and more urgently that “you shouldn’t have to live this way.”

“Because depression is often unrelated to external events, its opposite must be, too,” and its opposite is something like “...a life of curiosity, intrigue, and discovery…an ongoing process, driven by the desire to understand what makes life meaningful” So, not just meaning, but the continuing search for meaning. In a word: awareness—our birthright as conscious beings, the source of human creative genius—and also of the boundless pleasure in being fully alive.

I did escape death—of course not in the end, but in the beginning. Heroin death, motorcycle death, the death of drinking every day, pharmaceutical death, the death of loneliness, the death of not being known—and also, in a way, the younger, sad, small, anxious, fearful, addicted me did have to die, to make way for the flourishing of a much larger, more complete, and more vibrant self. Now, I feel the full flowering of creative freedom rising like tectonic heat, transforming my inner geology from silt and sandy sediment into granite lined with quartz, gold, and jade.

This is the opposite of depression: unbreakable, earthly, glittering treasure.

As I worked to complete the final section of this book, I dreamt of that same love of mine that asked “who holds you?” looking up at me as I stood on a dais, surrounded by dancers and drums. A scene straight from Tintin’s Prisoners of the Sun that I read to rags as a boy—she’s a priestess in a jaguar robe, an emerald at her throat, and she wears the ring we made together, two arms of pure, soft gold cradling a raw, uncut, pink diamond.

The ceremony that she leads is a blessing, of me.

This is the dream that has replaced the never-ending chase.

Still out on the road, a month after receiving her message with that question, I was camped again in my van in the high mountains of Colorado, alone, in silence, and entirely content. Salty with sweat and tears from a day of grieving as I ran along the trail for yet another relationship having ended, I put down my pencil, closed my notebook and rolled into my bunk. I lay there in the dark with the roof vent open to the sky, listening to the movement of the trees and the gentle hum of the little fridge as the wind settled, the stars shone brighter, and the coyotes sang their midnight moon song.

That was when I knew I’d gotten somewhere new. I had to learn how to get there, and it took me a long, long time, but now I don’t hesitate to say that I do know what it feels like to be myself.

It was a hard-won peace.

If I had one wish, it would be to have known earlier just how possible it is to change, and how quickly—and so, I wish the same for you. Accept no false assurances, trust your own self, listen for the gold that rises up from deep within, and use that to build a home for your soul. Let my story be evidence enough that it is possible to live free. All that’s required is to listen—and then, go!

⭐️⭐️ THANK YOU FOR READING ⭐️⭐️

Collectors Edition

This is the final chapter of my book-length memoir AN ORDINARY DISASTER, one man's proof that we can all learn to listen to ourselves, and to act upon the inner voice of our self, our sanity and our soul.

Needless to say, this is a major milestone for me, and I’ll have a lot more to say about this book project and my next steps towards publication in the weeks to come. For now, please enjoy, and, as always, I’d love to hear your comments.

Especially if you’ve been following my work with interest, now is the time to become a paying subscriber. Paying subscribers will be able to order a FREE* copy of the first collector’s edition of the book (you pay only shipping), and, also, just as importantly, your commitment will show your appreciation for the work I’m doing here, and your support as I move into the next chapter of the book’s journey.

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Further reading

The Earth Has a Soul: The Nature Writings of C.G. Jung — C. G. Jung

Lost Connections, Johann Hari

What Is The Opposite Of Depression?, Ricky Derisz

I’ve got some questions for you

1. How would you describe the opposite of depression?

2. Have you ever felt changed enough to feel like a new person?

3. What is your relationship with your own intuition?

4. How do you move through the world—with a lot of deliberation and anxiety, freely and without hesitation, or somewhere in between?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

I’m glad you’re here! And—this is a reader-supported publication. If you appreciate my work, please consider becoming a paying subscriber. As a full-time working writer, I appreciate every reader—and everyone who chooses to part with five bucks a month to support my writing. Almost all of my Substack remains free, but there are a few things that I make available only to paying subscribers, like my long-form handbook on intuition.

My mother was not a woman—that is, when I look back at how I remember her as a young person, I see mom, of course, but not a woman.

I’m sure this is common enough. Because of the psychosexual juxtaposition between mother and woman, I imagine it’s rare to be able see one’s mother as having much in common with the magical creatures that stoke the fires of men’s dreams—but still, all mothers are women, and, as I said to a young friend recently, it seems we’d all be better off if we could see that “she’s not just your mother, she is a woman—and the first one that you will ever know.”

My mother is many things. She’s highly intelligent, well traveled, and interested in the world. She’s caring, has a wide network of friends, enjoyed a series of careers, and has had her share of love in the world, having married twice and a few lovers in between. She wasn’t downbeat or cynical, and my mom enjoyed physical activity and the outdoors more than average.

She seemed to live in a neutral space, distant from the womanly realm. There was no musical laughter, sly wit or waggling finger. There was no music or ritual in the house, and no sense of the blood or fire that runs through the feminine world. I got no sense of who she was as a human animal. Despite her lifelong passion outdoor activities such as sailing and hiking, my mother seemed detached from her physical self—and I would say from her unconscious as well, because I could not sense who or where her soul had gone, or even if it ever was. The platitudes that I’ve complained about came mostly from her, and when she asked me “how are you?” I rarely felt that she expected, or would know what to do with, a truly honest answer.

I used to think that I was depressed because of a lack of fathering, and that is as true for me as it is for most men—but it was my mother that passed her anxiety—and her own version of depression—on to me. I’m not talking about so-called clinical, stuck-in-bed depression, and not even so much of the standard daily drag that so many Americans carry around. It wasn’t quite like “living in a cave of death,” as one friend suggested, although others have intuited from my stories that I grew up with a depressed mother, so something is clearly coming through.

Whatever it was that afflicted her, the result was that the field between us was lifeless.

No wonder I started out depressed. Now I know that it wasn’t just my relationship with my father that contributed to me being so angry and alone—and to my ambivalence about having children.

Really, I had no choice—I had to run, because I didn’t want to end up like my sister, or my father—or my mother. Alive, and highly functional, but cut off from the sensual world. I didn’t know many other adult women as a young person, but I do remember some whose colorful, womanly aliveness easily bridged the gap of generations—an art teacher at high school, the wife of one of my fathers’ friends—even young Princess Leia from Star Wars, with her knowing, sly and sexy smirk. I don’t know if it was within her, if she held it back, it was just naturally repressed in dealing with her teenage son—but my mother showed none of that. Of course, it’s not that I wanted or expected any sort of specifically sexual material to arise between my mother and I; nor did I ever consider asking her to show me her naked breasts, as Stephen Dunn imagines in his poem The Routine Things Around The House, and perhaps it was because, as it was for Alan Watts, that “I was disappointed in the fact that she did not seem to me as pretty as other women.” Whatever the cause, what seemed to me to be a total disconnection from her feminine self still echoes in my psyche.

My recurring dream of running and trying to get away—that was me, but in way, I think it was also her dream—and the message was the same for the both of us.

In depression, of course we wish to escape the pain of being depressed. She wanted to get away too. The thing is, there is no escape—or not simplistic escape, no running away. We can sometimes get away from the symptoms of depression temporarily, but there’s no running from the root causes—silence, lack of truth, lack of connection with other people and with the unconscious—without doing the work to shake hands with those shadows.

Now, that dream is gone, and I can see what it was trying to tell me all this time. There’s never just one single correct interpretation of a dream, but the characters in a dream usually can be seen to represent parts or versions of oneself. The dream was telling me that I was trying to get away from parts of me—and there was pain there, but those parts had some important things to tell me, and the pain was from not listening. I was trying to get away because I didn’t want to hear what they had to say.

Those dreams had all sorts of kind and useful messages for me—that it’s OK to stick around a bit and be the Frisco Kid; that I need to be outside more; that it would be good for me to drink less; that I should remember that I wanted to become an artist—but also, something more, and something deeper. I spent many years wishing for relief from what I felt while also feeling certain that I not only wouldn’t but couldn’t do whatever might be required by myself. In those dreams, I was afraid that what was chasing me was depression, and that if I let them in close enough to hear, that that would make it worse. I was afraid of the monster, so to speak, when I should have been speaking with the monster.

That’s the indirect nature of dreams. Instead of stopping to listen, I ran, and so those demons could not help me—and I was left to do ‘it’—life, that is, by ‘myself’—that is, without them, without my whole self. Not surprisingly, I found over and over again that I could not.

Only once I stopped running from those friendly little monsters, and allowed myself to listen to their messages could I integrate them into who I am. I had to stop and let them catch up, so that I could get the message—which was that to make progress out of depression, I would have to change how I was living—and I would actually have to do it myself. I mean, of course, who else—but I’d already been alone so much that, for a long time, the prospect of doing even on my own more just made me feel even more sad and alone.

Jung also often uses this concept of compensation to explain what dreams are trying to transmit. It’s no surprise then, that the solution to my recurring dreams of running was, in a way, to actually start running, which is what eventually led to me getting sober, and to rediscovering my creative self. The dreams of running, in the dark, chased by robots were compensating for a lack of real running, out in the sun with my feet on the ground.

Feeling more whole now, I feel more able to do things by myself—or otherwise—and, having gotten their message across, my pursuers have, for the most part, given up their chase. Those unconscious energies are available for other things now—for creativity, and for other messages.

From as early as I can first remember being interested in girls, my heart began to ache for love—and for touch. Of course, there’s no reason why feeling so deeply affected by the heart might mean that I’d be any less pulled by the body. In part because I was running from my mother, who did not seem to be much of a woman, I had no idea what I wanted or needed in a woman—or how to love one. I didn't have that first example of what a woman was, and so, even though I’ve gone in for love again and again, I did so not quite knowing what that was actually made of.

I didn’t know what I was looking for. I just had to risk it—and to their great credit, I have an army of loving, and mostly forgiving sisters from the many chapters of my life. I feel them all around me, but there were so, so many endings. There was a cost. Some pieces of my heart, and, certainly, some of theirs. So much sadness came with all that joy.

I knew before Kate and I split up that I had a pattern with women that was rooted in an emptiness that I felt whenever I was asked about love. I couldn’t really say clearly what love meant to me—and I was still looking for a woman to teach me. Many tried, but they could only do so much.

I was stuck, and it took another man to suggest to me that I couldn’t learn how to love while I was in love, trying to do the thing that I didn’t know well enough from the start. This teacher gave me an assignment which I agreed to a readiness that came from a deeper knowing that this was part of the work that I had to do, alone. I adhered to a fast of sorts for a year entirely apart from women. That meant no sex, no dating, and only minimal contact with women at all—something that might seem absurd or undoable at first, but soon enough becomes second nature.

Not only did I turn off the dating sites and apps during that year, but whenever I found myself coming into regular contact with a woman, I’d change it up. I switched to a different yoga class taught by a guy. If I was out somewhere getting coffee, I’d avoid anything but cursory interaction with women. Most of all, I sought male friends to replace the women—mostly exes—that had surrounded me.

I had to leave them all to break the cycle. Alone at last, I found love welling up from within me. I felt love in a new way, not coming from anyone else, but as an energy of my own, and, eventually, something that I began to understand how to transmit. For whatever reason, that was what I hadn’t absorbed from the first woman in my life—my mother—and so I had to learn it later on.

⭐️⭐️ THANK YOU FOR READING ⭐️⭐️

References and Further Reading

• The Earth Has a Soul: The Nature Writings of C.G. Jung, C. G. Jung

• Belonging: Remembering Ourselves Home, Toko-pa Turner

• The Routine Things Around the House, Stephen Dunn

• My complete “for men” reading list.

I’ve got some questions for you

1. How do you see your mother, as a woman?

2. Do you have any recurring dreams?

3. What have you been trying to escape?

4. What message might whatever it is that pursues you have for you?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

My face twists with disdain at the weak and false reassurance of any platitude. They may be offered with the intention to soothe, with an answer—any answer—but these careless, easy, empty lines show a lack of listening, a lack of insight, and a lack of attention. Receiving one of these hollow clichés feels like being smacked in the sauce with an wet, smelly sock. It’s a smothering form of mothering—a silencing, and a cowardly way of saying “I don’t know, and so, please shut up.”

The heat of my inquiry refuses to be placated. There’s a hole in my heart, and it hurts.

My mother often offered me this kind of stale, old bread. I’m sure she meant no harm, but her lame replies starved me for love and truth. It was always obvious to me that these are the lies we tell when we don’t know how to better approach the “insoluble problem of being a person in the world,” as put it. Not that it was for my mother—or father—to solve that problem for me, but it was a shame to see them not knowing, themselves. Or so it seemed.

Yet another wad of cheap chewing gum, another oversized corner-store candy bar; the Kool-Aid and the Peanut Captain Crunch and the Atari console that we didn’t have as kids but that were fed to me anyhow in the form of the infantile, idiotic, and incomplete idea that I could be “anything I want,” or that everything “would be OK,” even though “life isn’t fair.” Lacking explanation or instructions, all of this sounded misleading—and dumb.

I knew they were lying, and so did they—not because these things aren’t true, but because they aren’t the whole truth. Thanks so much to what my parents did teach me, I never doubted my ability to get things done, but I had no faith in the longer run of years.

You can be anything—or anyone—you want to be, provided that you begin as someone. Lacking that foundation, there is no ground for growth. Instead of a burning shore, it’s a wasteland. When I looked inside, I could not locate a solid center. I lacked soul confidence.

Over time though, simply by paying more attention—and by learning that I actually preferred not to dull my senses, and by writing down my thoughts, and by taking myself outside more and more—no longer running from anything, but running in the wild, in the mountains, in the woods, running everywhere I went—and by not skipping over messages when they did surface, I did finally learn to pay attention to the voice that was speaking my self. As I did, I began to feel a subtle warmth rising up and filling some of the holes that had always felt like part of me.

No wonder my father loved Swiss cheese. I can’t even find the stuff he liked any longer; tasty—and so full of holes that half the weight of each block was missing. Half cheese—and half empty space.

The warm feeling in my chest is what I got in exchange for finally paying attention to the part of myself that speaks without words. That glow is the unconscious saying “thank you for listening”—and it’s a feeling that invites the ear to turn still closer. This warmth of gratitude for being heard is what it feels like to be someone, and it’s what I’d been missing all along.

This way of listening is part of what we must teach our children. It may be the first thing we must teach them. It may be the only thing we need to teach them.

Since I did not learn early on, I had to teach myself. I’ve had many lessons—many lovers, many brothers, many books, many journeys—and, when I think about where I’ve learned the most, most of all, it’s been while running, and writing. Just as Murakami only stopped smoking because he had taken up running, in the end, it was wanting to run that got me pointed in the right direction.

It wasn’t so much that I got to the point that I had to quit doing things that didn’t feed me—I did, but more than stopping, it was that I started doing things that I liked better than erasing, forgetting, and escaping. When I did quit, it came last—or almost last—because the one thing that came after quitting drinking was that I fully remembered my long-held goal of becoming a writer, and finally began to pursue that transformation.

And so: first running, and better health, then sobriety, and finally writing. That final call came forwards more and more in my late forties, but it was not entirely clear until May of 2019, when the words “I’m here to tell the truth” rose up from deep within. I’d known that I wanted to write, but it wasn’t until then that I realized that I had to “sing from the very wound that you’ve worked so hard to hide,” as Toko-Pa Turner puts it. I began then to write myself into existence.

The result of all of that running and writing—and many other things—is that I trust myself now. Now I know, not from someone else’s bullshit rhyme, but from my own lived experience, that things do tend to work out—and damn well, in fact—and that is what gives me real confidence. Life has only gotten better over time, and the more I pay attention to the subtle signs, the more often I am delighted—and not entirely surprised—at how it’s even better than I could have imagined.

Now, all of those long-dead clichés feel true, not because I think that I can be President, or an astronaut, or a movie star, but because I have proven to myself that I am capable. Not of everything, but, yes, of anything. I never have before, but if the need arises, let there there be no doubt: I can fly that plane.

That inner voice—call it intuition, call it the voice of self, call it whatever—that was the voice that was missing, and once I learned to hear it, I finally felt that I could not only go with confidence, but I was willing to do so, alone—as we all have to, in the end.

The fear is gone.

This is part of my book-length memoir AN ORDINARY DISASTER, one man's proof that despite what may seem like our inability to hear it, and all of our attempts to avoid it, we can all learn to listen to ourselves, and to act upon the inner voice of our self, our sanity and our soul.

Especially if you’ve been following my work with interest, now is the time to become a paying subscriber. Your commitment will show your appreciation for the work I’m doing here, and your support as I move into the next chapter of the book’s journey.

Become a paying subscriber

Further reading

Belonging: Remembering Ourselves Home — Toko-pa Turner

I’ve got some questions for you

1. What are some of the awful clichés that you’ve heard most often?

2. Are there any of these platitudes that have served you?

3. Was there a particular time, or way, that you started feeling like someone?

4. Can you fly that plane?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

This conversation is part of a series of interviews with various brothers and teachers, including many fellow writers, all of which are part of the body of work surrounding my book-length memoir An Ordinary Disaster—one man's proof that we can all learn to listen to ourselves, and to act upon the inner voice of our self, our sanity and our soul.

An interview with the author

My friend Michael Lipson interviewed me recently about the development and writing of my book-length memoir An Ordinary Disaster.

I'd love to hear from you after listening, so don't be shy about leaving a comment or a question.

Use the Substack audio player at the top of the page ⬆️ to listen to the interview.

Highlights

13:39 …how it's possible to forget something as important as what I was supposed to be, and then, a long ways down the road, come back to fully remembering—not coincidentally, a the point when I was also finally in a position to pursue that.

14:39 What was it like to begin and what were you seeking by doing that?

15:19 …part of the reason that writing began to resurface was my experience changing my relationship with alcohol.

17:19 I was asked to state my purpose and I said, “I'm here to tell the truth.” That felt true, and a very clear, spontaneous expression of the answer to the question of what I'm here to do in this chapter of life.

19:59 I was tired of feeling like I wasn't expressing myself—and also that I didn't know how to.

21:09 I felt like I needed to speak myself into existence.

23:09 …The process of ‘becoming a writer…’ “I had to let the material work with me.”

27:09 “As I confronted myself with the truth…that cemented my sense of self...”

36:09 …having people that I've known for a long time read my work has “made me feel like another person, like another whole part of myself is alive and present and being seen and active in relationship.”

40:39 “I now have the confidence that I am doing what I should be doing and I will get where I'm going by being myself. I don't really have to think about it much at all. I just now am able to be myself, and let that lead.”

43:39 Q: Where is the book in terms of the pathway of Campbell's hero's journey? A: The book is the return, the gold, the treasure.

46:10 “The creative act is a form of dreaming. When I'm writing and imagery or metaphors come in, it's the dream state—it's the colors arising from the unconscious psyche.”

64:09 “…intuition refuses to be named because it's a function of the unconscious and therefore it cannot be named directly. It’s a defining characteristic of working with anything in the unconscious—the shadow, intuition, dreams. You have to move towards them indirectly.”

1:13:00 “the spiritual power of sport is hugely underappreciated. Outdoor sports have been the primary path to reconnection with myself, and to wayfinding in my own life in a way that feels whole and satisfying.”

1:15:00 “you tell the story of how you responded to those things as you’ve aged, and I see this as you’re actively wrestling with de-adulterating yourself and getting to your pure state. ... the gravity field is reducing, and your presence, your aura, your perimeter is expanding at the same time...”

⭐️⭐️ THANK YOU FOR LISTENING⭐️⭐️

Thanks 100K to my dear friend for the interview! Michael is a master coach who has worked with hundreds of leaders and executives, as well as a leader in the world of mens work, through his involvement in EVRYMAN and the Young Men’s Ultimate Weekend.

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Further Reading

Questions for you

1. Which parts of the interview hit home for you most?

2. Have you ever forgotten something for many years, and then remembered it at a later time in life, perhaps when you were more capable of realizing that dream?

3. How has your relationship with the naked truth of your own life evolved over tim, and how has that affected your sense of self?

4. Where are you in terms of Campbell's hero's journey, in your own life?

5. Have you experienced the spiritual power of outdoor sports?

6. Have you ever experienced a time of a dramatic sense of coming more fully into yourself?

Leave a comment

Before I knew anything else about myself, leaving was the only thing that felt like me, and escape seemed like the only thing that mattered. Naturally I wanted to escape the house to get away from my parents’ control, but also to get away from the disruption and chaos swirling there around my sister. I also wanted to escape San Francisco; as proud as I was to be a native son of the City, and as attached as I was and still am to its unique and compelling geography—in those early years, even just crossing a bridge to Marin or the East Bay was a minor treason, and any mention of the arch-enemy of “LA,” which might as well have been most of the rest of the state of California, was out of the question. I was also stricken, and sickened, frightened, and exhausted by the plague of alcohol, drug, and violence-related injuries and deaths of my peers. I viewed San Francisco through a lens of love and death, a forever home shrouded in darkness that I constantly and feverishly worked to separate myself from.

Amongst those of us that did survive, there are many of my friends that purposefully left so as to distance themselves from this same dark past. I left in many ways, and many, many, many times, and yet now find myself here after all, happier than ever to be part of what is now a lifelong community—family, really—that began going back to elementary school—and still, I dream of leaving.

As I’ve said elsewhere, if nothing else, we get good at what we do, and I got damn good at leaving—so good that it became part of who I was—a core aspect of my personality and of how I was known to others. I was always leaving, and returning, and leaving again, touching down for a few days and then winging off somewhere else, and I reveled in what felt like the freedom of it, as well as the delight of finding my way around the world.

I’d return home for a while and then soon enough I’d find myself yearning or ready to leave, and then, before I knew it, in a familiar-smelling cab on the short run down 101 to SFO, threading my way through the airport maze, and then settled in my seat for takeoff, excited at the prospect of, if nothing else, collecting another minor chapter in my never-ending saga of points visited around the globe. I’m fond of saying that “I’ve been most places,” and it has made for some good material, but the fact is that almost always, once I did get away, soon enough I’d end up lonely, confused, and low again, wishing for a woman and a home—anywhere but here. I could not come to terms with the idea that one place, especially not the place where I’d already spent so much time by way of having grown up here—San Francisco—could possibly be the home that I needed.

In leaving home, I was searching for home, and yet unable—or unready—to see anywhere as home.

In early June of 2019 I packed up my apartment, put my things in storage, and drove east, headed for the Sierra Nevada. I have a photo from my parents that shows me lying in the pine duff of Tuolumne Meadows as an infant, perfectly happy and already accustomed at the age of three months to the ethereal alpine atmosphere at nine thousand feet above sea level. Those mountains run so deep in my blood that I have memories of those places even from before I could form memories, and so it’s often no more than to the mountains that I need as a destination when I go. As in fact yet again today, as I write these very words.

Over the course of the last several years and even more-so over the few months prior, I’d left everything from my past behind—my business, the most peaceful and loving home—and relationship—that I’d yet been blessed with, and—more than a year ago already—my lifelong love affair with drink. I was leaving again, but this time was different. I still felt the sense of inevitability, the pull of the road, an echo of my addiction to leaving that makes it perhaps too easy to leave, but now I know that I don’t need to leave, and I’m more comfortable than ever with the idea of making my home here, or somewhere. Much as with alcohol, I changed my relationship with leaving. I am still attached, but no longer addicted.

I made quick tracks across the flat, smogbound, overheated gap of California’s central valley, turned south for Fresno, and then east into the foothills. There, I spent several nights amongst the domes and valleys of a place called Tollhouse, where I joined several fellow pilots to fly our gliders high into the faultless azure sky, craning our necks over our shoulders eastwards toward the snowy peaks of the southern high Sierra. From there I drove north, around the west side of Lake Tahoe past Emerald Bay, north through Susanville, and then west through miles of plantation forest—still beautiful in its scale—to Mount Lassen and the Hat Creek Valley.

My van is smaller than most of the larger ones you might see out on the road, and I like it that way. It’s a fine little land yacht with a lovely custom bamboo bed frame, a solar-powered fridge and a little table that folds out when I need it. Traveling in the van is as simple as: find a meadow and park along the edge, cook some beans, crawl in the rack and sink into sleep, already dreaming of morning coffee. I often sleep better in that little can than at home in my own fine bed, and the freedom—the freedom!—to turn the key and roll on with the road and the wind—often, that is exactly what my body needs.

Movement is part of who I am. I need to move my body, and I need to be free to explore, to roam, to wander—and to find my way. Although we don’t often think of journeymaking as a skill, it feels to me that it’s one of our oldest trades, and a craft that I’m proud to be an expert in. Even though some of my own travel may have been needless and even addictive escape, it’s also true that I’m always ready for adventure, and more capable than most of cooking one up.

More importantly, all that leaving has offered me a certain kind of cleansing, and release. The practices of making ready with clothing and equipment so as to be just ready enough, while also knowing that there may well be something left behind, and also that that something is immaterial—and of the leaving the always larger set of belongings and physical shelter and comfort and static safety of home for the fluid and mobile and much more self contained, much smaller home that is carried with oneself while traveling—train us to have our affairs in order, know what is needed, let go, make do with less, intentionally move into the unknown, and, most of all, offer oneself shelter from within—and these meditations all derive naturally from movement and travel.

Continuing north from Lassen and Shasta, I joined a paragliding competition in the Applegate Valley, in southern Oregon, and then wound my way through the mountains north of there, stopping every day to run in the woods, swim in a creek and then soak up the sun. The Rouge, the Umpqua, the Willamette, the Colombia, and the vast meadows of the Malheur all passed before me and beneath my wheels as I rolled onwards.

A couple of weeks later, I found myself at a place called Priest Hole, a sage and gravel bend in the John Day River in eastern Oregon, on my way to Colorado. The glow of the sunset had faded over the scrub oak and the many-colored mesas and the silent, oily slide of the river, and I was at my little table, listening to the evening birds and writing in my journal.

I was writing the beginnings of what would become this book.

Sitting there inside my little rolling home—so tiny that I can’t even stand up inside—a message came to mind that I’d gotten a few days prior from a woman that I had once been engaged to.

“…isn’t it hard in moments without alcohol?” she wrote. “Who holds you?”

Of course, at one time it had been her that held me, but what became clear right there and then was that in the entire month since I’d left, on the road alone and with no permanent address, not once had the thought of home crossed my mind. I’d passed through—and beyond—my place of often-desperate and always-seeking need—and my answer to her question was, “I hold myself now.”

Now is the time

This is part of my book-length memoir AN ORDINARY DISASTER, one man's proof that despite what may seem like our inability to hear it, and all of our attempts to avoid it, we can all learn to listen to ourselves, and to act upon the inner voice of our self, our sanity and our soul.

Especially if you’ve been following my work with interest, now is the time to become a paying subscriber, to show your support as I move into the next chapter of the book’s journey, and of my journey with it.

Become a paying subscriber

Readers, fellow writers—if you want to support what I’m doing here at my work, now is the time to help spread the word!

Share An Ordinary Disaster

Further reading

I’ve got some questions for you

1. What’s your own relationship with leaving — and with home?

2. What do you feel is the value of travel, and is getting good at it something that has real value?

3. Who holds you?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

I’m glad you’re here! And—this is a reader-supported publication. If you appreciate my work, please consider becoming a paying subscriber. As a full-time working writer, I appreciate every reader—and everyone who chooses to part with five bucks a month to support my writing. Almost all of my Substack remains free, but there are a few things that I make available only to paying subscribers, like my long-form handbook on intuition.

There’s a singular dream of mine that I’ve had for as long as I can remember—a dream that I’ve had at least a thousand times. The details vary with the night, but the dream is always about a chase. The version I remember most vividly is from my twenties, and, as it is in dreams, the image arrives fully-formed. All at once, I find myself swinging through the treetops of a primeval forest so vast that it forms an entire landscape all by itself.

This endless expanse of impossible trees, each even larger than the massive redwoods of California, shapes a fantasy world through which I move like a monkey in a sea of leaves, past treehouses suspended from giant branches and huge flowers overhanging, dripping with wetness and life, precious sunlight streaming down from the canopy far above.

Far below, on an old road gone overgrown and shady, a small humanoid robot lopes along, pacing me as I move through the tree-tops. The machine is following me—not quite hunting, but it feels important that I stay ahead. I ape along from vine to vine and from brown outstretched limb to massive limb, thick and wide as a whale’s back, and then again, below, I catch another glimpse of the square metallic head and glinting electronic eyes turned upwards as they track me. A small red light pulses, seeking.

Already half-erased by florid growth, the dream road below me is like the road that ran from our house in Maine up through the woods to the sloping back field overgrown with wild blueberries. This was the road that I walked, and these were the woods that I ran through as a boy—then of course, not pursued by anything at all. In the dream though, I must move continuously to remain out of reach of my pursuer. I’m breathless and excited by the chase, and while I’ve ever quite been caught by whatever it is that’s tracking me—in this dream, in my haste, I miss a step, my feet slip off a branch, and then I’m falling.

When I was just sixteen, I wrote about this same forest in a youthful homage to the eco-futurist worlds built of words by writers such as Ursula K. Le Guin and Larry Niven, and in a tattered copy of Ernest Callenbach’s delicious—and very unlikely—Ecotopia. In my own story, I wrote of a home high, high up in these otherworldly trees, and, just as in my dream, the entire universe of that world was forest, like a green God all around me.

In other versions of the dream, that forest landscape has instead been a foreign city, a mansion of many rooms, or a jumble of giant colored blocks, and other things have taken the place of the robot: a tiger, a swarm of bees, a group of muscular parkour athletes—but whatever shapes these symbols take, they’re always after me.

I take a Jungian approach to the interpretation of dreams, according to which everything that appears in a dream originates in my own psyche, and also that, of course, there is no one fixed or correct interpretation. Like a spread of tarot cards, the meaning is whatever emerges from the reading of the images in the moment, and will appear differently at different times. Several different meanings can all be true, simultaneously.

Most often, and most of all, this dream feels like an anxious threat. The dream is also an expression of another major theme of this book—the primal importance of physical movement and adventure, outside, in the natural world. The character in the dream—which of course is always me—is always running, leaping, swinging, moving—and he is being pursued, or driven, one could say, not only to escape pursuit, and not only to simply move, but to be going somewhere and doing something.

He’s driven not just to escape, but to reach some goal, to accomplish something. The clock of life is ticking, and the dream is an expression of my basic drive to do something meaningful enough to satisfy what or who is pursuing me—which of course is also just another part of me. As Michael Meade has put it, “We are hunting our fate, even as we are pursued by it,”⁠ and so in this so-often-recurring dream, that part of myself that is my fate is pursuing me, pushing me along so that I may become someone.

I think it also shows, perhaps more than anything else, and just as it was for Le Guin, that for me, the word for world—and for home—is “forest.”

There’s only one other thing that has recurred so often for me as this dream of pursuit—and that is the feeling that I’ve written about so much here: the feeling of I don’t know, that I don’t know what to do, and that I can’t…at least not alone.

Just like this dream that has been with me for decades, that feeling has also come to me a thousand times and more, with its own message of unknowing, blockage, statis, and of terrifying loneliness, mental static, and paralyzing fear.

Now, only now, near the end of this story, that dream is gone—and so is the feeling of not knowing, along with the anxiety, the fear, the running, and the need to escape.

Now is the time

This is part of AN ORDINARY DISASTER, one man's proof that despite what may seem like our inability to hear it, and all of our attempts to avoid it, we can all learn to listen to ourselves, and to act upon the inner voice of our self, our sanity and our soul.

Especially if you’ve been following my work with interest, now is the time to become a paying subscriber, to show your support as I prepare The Final Chapter and move into the next chapter of the book’s journey, and of my journey with it. Paying subscribers will able to order a copy of the book (now, or later) for just the cost of shipping, and, also, and just as importantly, your commitment will show your appreciation for the work I’m doing here, and that we all do together.

Become a paying subscriber

Readers, fellow writers—if you want to support what I’m doing here at my work, now is the time to help spread the word!

Share An Ordinary Disaster

Further reading

• Inner Work: Using Dreams and Active Imagination for Personal Growth by Robert A. Johnson — a manual for Jungian dream interpretation and other inner work.

• Belonging: Remembering Ourselves Home by Toko-pa Turner

• Ecotopia by Ernest Callenbach

• The Integral Trees by Larry Niven

• The Word for World Is Forest by Ursula K. Le Guin

• Michael Meade’s Living Myth podcast — Episode 341 — A True Path in Life

You might also enjoy some of my other writing on subjects mentioned here, such as:

I’ve got some questions for you

1. Do you have any recurring dreams?

2. How do you interpret the meaning of dreams?

3. Is there a word that means “home” for you?

4. What’s your own favorite forest world, fantasy or otherwise?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

By the time I got back home from Manila, the hole in my finger had started to heal—but it was still just that—a hole, ringed in dead, black flesh, and as I’d already known subconsciously when I pushed in the pin to puncture that little blister, the wound would heal, and also: it would be with me forever as a permanent scar.  Maybe I was trying to give myself a mark.

Something had been coming to the surface long before I’d flown off to Hong Kong and the islands of Papua New Guinea. I’d say I didn’t know what it was, but most of the reason why I didn’t know was that I didn’t want to know. I didn’t even want to know that I didn’t even really want to go on that voyage on Discovery—but as I’d done so often before, as a lifelong escape artist, I ignored what I didn’t want to know—and then I went.

While the sailing trip had been much too tame to offer any real stimulation, let alone adventure, I still had some other cards to play that winter in terms of getting out in the world. Barely a week after I’d returned, my girlfriend and I flew back across the Pacific to Japan, where we spent two weeks trekking between ramen stands and sake bars. After that it was back to San Francisco again for just a few days, and then I flew to northern Brazil to work there as a guide on two long distance kitesurfing trips, eventually returning home again by way of a stop in New York for Christmas.

All of that meant that until New Years at least, I was running on a steady infusion of physical exertion and, if not full-on type-two misadventure, there was certainly no shortage of real experience, exploration, and excitement. I love California, and I love San Francisco, and just as much as I love being at home, I absofucking-love-love-love traveling, living and working in foreign countries.

When I finally did return from all of those other places, I climbed the stairs of the apartment that I shared with Kate, happy to be back—and already feeling wary of what I’d find there. I took my bags into the bedroom and laid them open on the oak slat bench that my father built nearly fifty years ago from lumber he felled in the same woods in Maine that I ran through as a small boy. The cat came in to keep me company, rubbing her furry belly and wrapping her soft tail around my ankle before curling up on the bed.

As I removed the evidence of my wandering, I felt all the delicious exoticism and jet-travel euphoria draining away—replaced, minute by minute, by an all-too-familiar and yet still formless dread, a pervasive sadness, and, most of all, that old feeling of not knowing.

There was nothing really wrong with how things were for Kate and me, but now that I was home again, and as long as I was there, I was faced again with what had already been becoming apparent before I’d left. Kate wanted children, and although—yet again—I had been open to the idea when we met, when it came down to the doing of it, man, the truth was that I just didn’t have the heart. I’d been a lonely kid—and an angry teen—and, consciously or not, I’d constructed my life in large part to avoid the commitment, constraints, expenses and challenges that I saw so many of my friends struggle with as parents. As with so many others who have chosen not to have children, I appreciated the time I’d get now and then with other people’s kids—and I knew that I could be a good father—but the idea of being dad on a daily basis well, sometimes it was terrifying, but mostly it just wasn’t what I really wanted—and it wasn’t congruent with how I was living.

Even so, I considered, yet again, the possibility of saying yes. I tried to ‘embrace the one-hundred percent,’ as it came to me at the time. I made it a mantra—and still, before long, it became clear that I’d have to let this woman go, so that she could realize her own dreams that were not my own.

I was also faced with the reality that despite having just returned from three months of travel, I had two more overseas trips coming up on my calendar, the first to Cambodia for a business conference, and then an exploratory trip to to Columbia with a fellow kitesurfing guide. As enticing as those felt, the truth was that when I turned my attention to the reality of leaving again so soon, my chest tightened and my eyes filled with tears.

Even with the divergence of our major life directions present in my mind—and no doubt in hers as well—Kate and I loved each other, and we were happy to take up life together again. After a calm and celebratory New Year’s Eve, in early January we had a little party with some friends where I got very excited about the abundance of good wine. I quickly found myself well aware that I’d become what the Italians call sbronzo, which I suppose translates best as having a heat on—and was left feeling gross and heavy the next day, green cartoon gas bubbles urping from my throat up into the frame above my lumpy, constricted, throbbing head, like Captain Haddock in the old Tintin comics.

She went to LA with some friends the following weekend, leaving me at home by myself. For no particular reason other than because I was bored and alone and felt that I deserved it, or could get away with it, or didn’t really care, even with how I’d felt after the party—and even though I was due to meet a friend visiting from Europe the following morning, I had a bottle of wine and a couple of cocktails with dinner and a movie, by myself, and went to bed already knowing that I’d have to cancel on my out-of-town friend.

I spent the next day loafing at home and feeling sorry for myself—ashamed and embarrassed really—and I was still thinking about it that evening as I sat waiting for Kate to return, again on the sofa in our TV room. I sat there and for once, I couldn’t bear pushing the truth away any longer. I couldn’t bear it for myself—and not in the face of the honest love that I felt for and from this woman. I couldn’t help but feel stronger being with her easy-going goodness, and also that I owed her something more than another hangover story—and so I sat right where I was, and instead of turning away, I turned towards a reckoning.

It took some time to unwind.

The fact was that even with the good life that I shared with her, I was feeling depressed yet again, just as I had been before I’d left to go out around the world the last time—and that along the way—and since returning home—I’d chosen to drink more than I really wanted to on several recent occasions.

I’d been in therapy for years working to resolve the depression, which I’d never really thought all that much about, other than to be subjectively certain that far fewer people are actually depressed than the statistics—or the prescriptions—would have us believe. I’d done some reading on the subject more recently though, and as a result, I’d come to think of depression as what I call a “symptom of not living well”—not a predisposition or a chemical imbalance, but as a protest by the organism against how the ego is forcing us to live. A message from the unconscious. An expression of dis-ease.

I knew that I was in denial about how Kate and I felt about having children—differently, that is—and that living with that dissonance was part of the issue, but that didn’t feel like enough to lay me quite so low. Besides, my feelings of depression had been with me long before my relationship with her began.

I was frustrated that I’d ended up feeling depressed again, and that, as I saw it, I didn’t have a good enough reason to feel that way. At that point in my life I’d already changed just about everything about how I’d been living previously. I was healthier than ever before—trail running several miles and doing yoga and pilates regularly, eating well, learning to play the drums, and still living the high life less than three years after having sold my business. I felt healthier and more creatively alive than ever, and aside from our lack of alignment around having children, my relationship with Kate was otherwise stable, calm, loving, supportive, and fun.

If my unconscious, in the form of ‘depression,’ was trying to tell me that something else about how I was living was untenable, what was it?

It might seem like the answer should have been obvious, but it didn’t become clear until right then and there, as I forced myself to confront the reality of having flaked on my visiting friend, at having overindulged at the party, at having consumed too much alcohol in Japan and on my sailing trip in New Guinea. Seeing myself more clearly than ever before, I was able to receive the message that even though that had been me, that was no longer the person that I wanted to be.

The wound on my finger still hadn’t completely healed, and it tingled and itched as I sat there meditating on my situation, reminding me of my how a momentary lapse of judgement and care—could result in permanent damage. Even my finger was trying to tell me something.

I’d already changed just about everything about how I was living.

Everything, that is—except for my relationship with alcohol.

Thing is, I’d been focused on depression as what I was suffering from, not “drinking.”

I’d never been a really heavy drinker, and by that point I’d already been drinking less, and much less often than I had in earlier life—not so much by way of conscious choice to moderate, but because of other changes that were happening in how I was living. For one, I’d come to enjoy running enough that I often found myself prioritizing that over a third, or even a second glass of wine. I’d also started to become aware of a subtle distaste for having a drink in my hand so often. I wanted my hands free, and I wanted to be more free.

Even so, it had never occurred to me that anything less than catastrophically excessive drinking could result in a long-term effect on the psyche.

I remember my high school psychology teacher telling us that alcohol is a “depressant,” but I always understood that to mean that is was a physiological ‘downer’ in contrast to uppers like cocaine and speed—not that it could cause this thing called “depression.” Perhaps also because depression wasn’t something much talked about in those days anyhow, nobody ever suggested a connection between alcohol and depression as a persistent state of mind—not back in high school, not my friends or lovers over the years, and not in all my years of therapy.

Right at that moment, something came rushing to the surface, and then resolved into clarity like a winter pond suddenly reaching the freezing point and, in an instant, being rendered solid, and transparent, by a layer of black ice.

What if drinking was making me depressed?

Stunned into immobility, I felt the the weight of my body drop away as I stared straight ahead at nothing but the white of the walls. The realization that I’d been so naïve, so immature and ill-advised—and that there could be a real reason that I had spent so much time feeling so fucking horrible for so much of so many years—that realization pinned me to my seat and had me drawing long, deep breaths of shock—and of relief.

It was just a month before my forty-eighth birthday. I wasn’t born depressed, nor with a drinking habit. These two patterns co-evolved, and now it was becoming clear that I could work all I wanted on feeling less depressed, but that I had been ignoring the most important contributing factor. I wasn’t just suffering from yet another mid-grade morning hangover—I was suffering from a whole other type of much larger hangover for all those years. I wasn’t just feeling sick and weak that day—I was feeling the cumulative psychological sickness and weakness of all of those years of imbibing a depressant.

My body had spoken up in recent years about getting more active, about kiting, trail running, swimming in the bay, about selling my business—even about moving out of the city of San Francisco itself—and now my body was finally speaking up about depression and drinking.

Kate returned later that night, but I didn’t tell her of my epiphany right then, as I still hadn’t quite reached the point of taking action on that score. However, one thing that had become clear was that I couldn’t stomach leaving again so soon. As we were going to bed that night, I told her I’d decided to cancel those upcoming trips to Cambodia and Colombia, and I fell into sleep feeling lighter than I had since my return.

Less than a week later, we went to another party, this time for one of my friends from the kitesurfing scene at Crissy Field. Everyone was anxious to hear of our round-the-world travels. The host had sprung for a well-stocked bar, and I went straight for it, pushing past one of our local superhero sailors in my haste to get a drink in my face.

When I turned around, Superman was talking with another friend and his wife J, with whom I shared harmlessly flirtatious friendship. I’d ordered whatever Chip was drinking—tequila and ginger ale—not a bad combination, and it went down so well and in the company of close friends that I kept the five of us parked right there by the bar, and knocked back three more in quick succession. We all seemed to be having a blast, but as I was reaching for drink number four, one arm was around Kate’s shoulders, and the other was reaching for J.

She was always very warm with me—and also, gracious and respectful of our primary relationships. For my part, even more than however much I was attracted to her, she was a sister first, and so when I felt myself using my strength to pull her in, wanting to feel her warmth, I flushed with shame at my greed and released my grip, feeling sure that I’d overstepped. I saw a shadow cross her husband’s face.

I was suddenly overcome with a wave of exhaustion. We’d only been at the party forty-five minutes, but I felt woozy and lame. I turned to Kate and suggested that we leave, right then. My friends waved off my muted apology, and home we went.

The following morning, I shared with Kate something more of what had been on my mind that past week. I said that what had come to me was that “depression is like psychic heartburn”—we get it from being forced to digest things that are “incongruous with our soul.” I walked her through my subtle slip-up with J, the rapid over-drinking that had led up to it—and revisited the night of the other party, where I’d also had too much to drink, too quickly, and not enjoyed the result.

Bless her, because it was Kate that spoke up right then and there to say, “why don’t we take a break from drinking, just for a week.” Almost before she finished her sentence, I rushed to say, “Great idea, let’s do that,” and as I did, I was already thinking ’perhaps indefinitely.’

I’d never made a point of reading anything about alcohol, drinking, or addiction—or perhaps I’d made a point of not reading anything about it—but in that same week I found meaningful substantiation for the connection between depression and drinking in Johann Hari’s Lost Connections, a connection which was further confirmed several weeks later when I picked up a copy of a book called This Naked Mind in a bookstore in Aspen.

Like most people, I hadn’t had any words to describe my relationship with alcohol, aside from “drinking”—and the idea of “stopping” always seemed like it only applied to people who had a much more serious problem. Of course I’d known for many years that drinking wasn’t exactly good for me, but I’d thought all along that my problem was depression, and I’d remained focused on fixing that.

In the meantime, beer, wine and cocktails had been my lifelong companions. They’d taken the place of real friends—and of the wild outdoors that I knew in my youth. Drinking had given my body some real sensation—something that felt like something all of those years, and so for all those reasons and others, time and time again, I’d punted any real examination of my patterns around alcohol.

Even with the warnings I’d experienced—the violent and terrifying anxiety attack in my kitchen, the hit-and-run car crash, and, most recently, the necrotic infection on my finger—I somehow hadn’t gotten a clear message, or gotten it strongly enough. I’d always felt that my relatively moderate drinking wasn’t a real problem.

And perhaps it wasn’t—not all by itself.

Even more than the knowing, it was, again, my body that insisted on a change. My body was refusing to be depressed any longer, it was refusing to allow me to leave home again—and it was telling me that now, after all these years, it was time to change my relationship with alcohol.

For once, I knew something had to change—and I stopped drinking that very same day.

Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, one man's proof that despite what may seem like our inability to hear it, and all of our attempts to avoid it, we can all learn to listen to ourselves, and to act upon the inner voice of our self, our sanity and our soul.

Further reading

• Born to Run by ‘barefoot runner’ Christopher McDougall

• What I Talk About When I Talk About Running by Haruki Murakami

• Stanton Peele, Love and Addiction

• Dr. Adi Jaffe, The Abstinence Myth

• Annie Grace, This Naked Mind — my favorite book on how to change your relationship with alcohol

• Johann Hari, Lost Connections

• Caroline Knapp, Alcohol, A Love Story

• Marc Lewis, The Biology of Desire: Why Addiction Is Not a Disease

Here’s the table on contents for my memoir in progress. You might also enjoy some of my other writing on subjects mentioned here, such as:

or any of the other essays that you can find here:

I’ve got some questions for you

1. Have you experienced depression? If so, what do you feel is the root cause, and why?

2. What’s your own relationship with alcohol and how has that changed over time?

3. How do you know what’s right for you—and how has that changed?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

Flying into Hong Kong in the fall of 2017, I was pinned to the window, hoping to somehow catch a glimpse of the dystopian scene that I remembered when I’d first been there with my dad back in ’83—our 747 swooping low on approach to Kai Tak, diving between rain-spattered skyscrapers flashing huge neon billboards, the low sky crowded with dark, heavy clouds. More than thirty years later though, the old airport was gone, the city had changed, and I was no longer a teenage boy along on a business trip with my father. My fantasy image dissolved on the long taxi ride in from the new airport, and by the time I arrived at my hotel, I was lonely, jet-lagged, and crestfallen, reminded that I was off on what amounted to yet another expensive diversion—and from what I still didn’t quite exactly know.

I spent two days in HK nursing my back, drinking and wandering the humid, grey streets. Eighties Hong Kong had been a city of the future, ahead of much of the rest of the world, teeming with life, the sidewalks packed shoulder-to-shoulder like the camera gear that covered every inch of the walls of the camera shops in Tsim Sha Tsui, but the city of the present seemed like so many others run together by modernity, globalization and aesthetic trends made instantaneously universal by Instagram. I touched the past for moments, hiking the long steps to the misty peak, on the ferry across Victoria Harbor, and in the blocks of Wan Chai where washing still hung from windows above neighborhood markets with baskets of dried fish, but it felt like I was just marking time. I should have taken my stop there for what it was: a chance to visit a place that I’d been once long ago, without any expectation of going back to that time, or of having anything hugely striking somehow revealed.

After two days I flew to Port Moresby, the capital of Papua New Guinea, and then east to a tiny airstrip on the island of Misima to meet the sailing yacht Discovery for the last of a series of deluxe sailing and kitesurfing trips that I’d bought into a few years prior. By the time I stepped board, it had become clear to me that I needed and wanted something much more real and direct in terms of adventure, but I’d paid for the trip long in advance, and it seemed like a shame not to go. I was playing out the tail end of my time as a business owner, having told myself that I had the money and somehow deserved the extravagance in exchange for having worked away at something that I didn’t quite love.

The fact is, I felt like a rich tourist, and not a very bright one—a bit of an asshole really—for having spent so much for a vacation that I didn’t need, and without much chance of coming home with any sort of real story to tell, since the whole thing was planned and run by someone else.

Even so, after the three days of travel it has taken to reach the Louisiade Archipelago, I was about as far as I could possibly get from home, and despite the thick spread of luxury I was as thrilled as always by the radical dislocation and charmed by the raw, remote environment. I’d been on that boat before in Chile, Polynesia, Micronesia and the Marshall Islands, but the atmosphere here was different—perhaps also because of the mass of placid, superheated air that had settled over the islands around the time of my arrival.

As we set off, it seemed to me that the weather was conspiring to punish me for having no serious reason for being there. The sky was a heavy reach of deep blue with only the faintest breath of wind, and the sea, also calm, appeared lavender-turquoise, with low green smudges in the distance. The scene was unbelievably idyllic—and also dangerously lifeless. We drifted slowly from island to island, bartering bags of rice for fresh fruit with the locals and surfing tiny waves kicked up in the coral passes by the feeble tides. It would have been idiotic to imagine any complaint about our situation, but we were there to sail, and the wind was not cooperating.

The immense calm persisted, and by the ninth day, all of us on board were restless and drowsy as we floated in the sun-baked, limpid bowl of a vast atoll. Swimming was the only relief from the overheated, soupy air, and I didn’t hesitate to throw myself over the side whenever I felt my body temperature rising.

I felt an itch the next morning when I woke, and found a small blister rising on my right index finger. Upstairs in the cockpit, I had an early breakfast with the other guests, three Australian dudes in their thirties and an American 4chan type who’d gone bush in Sumatra. Still just after dawn, the heat caused a sort of sea-fog to rise directly from the surface of the water, obscuring everything beyond the rails, and leaving us suspended in a yellow-pink bubble glowing with gauzy sunlight.

As the sun rose higher into the morning sky, the vaporous haze was pierced by the bright calls of seabirds, and then opened enough to reveal the low, verdant tangle of a nearby sandbar covered in mangrove. Purple, blue and yellow fish rose and fed on tiny floating insects. The horizon remained invisible.

After breakfast, a lifetime of anxious habits with my hands drove me below to pierce and drain the blister, even though I knew it was better left alone. At lunch, the ship’s mate said I must have touched a free-floating stinging cell from a jellyfish, and that it would get infected if I couldn’t keep it dry.

I hadn’t noticed anything when it happened. I was tuned out, hypnotized by the stillness and heat—and it was impossible to keep anything dry. Even the air was wet—and what’s more, I was used to relying on my constitution. I put the mate’s warning aside, dove in again, and then slept through the silence of the motionless afternoon.

By the next morning, the pinhole in my finger had expanded into a round, angry wound the size of a pencil eraser, and dots of pink pus stained my sweat-soaked sheets. The mate produced a few capsules of expired Cipro, which I washed down with coffee, then beer in the afternoon. I wasn’t entirely unconcerned by the potential danger of an open sore in the tropics, but the end of the trip was approaching, and I expected that I’d be able to find a proper clinic as soon as I was back on dry land.

Later that evening, the hole in my finger had grown further, with a blobby black-and-white mass forming in the center. My finger pulsed gently as we played rounds of Spades and drank the last of my favorite tequila—Fortaleza reposado—that I’d brought along to stock the ship’s bar.

Two days later, we returned to the tiny, rusty port town from which we would fly back to civilization. My forearm felt tender as I climbed into the dinghy, and I noticed a cluster of evil-looking red streaks climbing past my elbow—a clear sign of septic infection. I drew a sharp breath as the ancient spectre of amputation sifted from the tangle of dark tropical forest crowding the shore. Mostly a threat of the past, but still, those arrows were headed for my heart.

As expected though, I was able to find a clinic shortly after returning to the capital. Removing my bandage for the nurse, I showed her what had now deepened into a shallow, bloody pit, edged in black, necrotic flesh. She wrinkled her nose and handed me fresh packet of Amoxicillin, assuring me that I’d be fine as long as I got it looked at as soon as I was Stateside.

My route home involved an all-day stopover in Manila before my flight onwards to San Francisco. Manila is mostly huge sprawl of grit and smog, but I’d been through there a couple of times, and I was proud of myself for knowing the city well enough to find some charm amidst the chaos instead of waiting it out in the terminal.

After a refreshing vegetarian lunch, I hopped from one patch of shade to another as the early-afternoon sun radiated down into the damp streets of Makati, making my way towards the The Blind Pig. Once I slipped inside, the quiet, shadowy interior was an immediate relief, set off by the crisp uniforms of the bar staff and the carefully arranged bottles and glassware glittering under low-voltage lamps.

The bartender nodded a welcome as I sat myself at one of the vacant tables, alone, and picked up the menu. Stepping over to where I was seated, the waiter couldn’t help but notice the crude bandage on my hand, and cast his gaze downwards with genuine concern.

“Sir, are you injured?” he asked.

Hidden beneath the winding of tape and gauze there was a raw, seeping cavity a centimeter in diameter. I could feel fluid from the infection wanting to drip down the back of my hand.

I lowered my eyes as he continued with solicitous caution. “If you’re taking antibiotics, it would be best not to drink alcohol.”

It was no surprise that he’d guessed—my finger was throbbing, and visibly inflamed—and it wasn’t just that I wanted a drink more than I cared about risking part of my finger. After two weeks away on a trip that I shouldn’t really have taken in the first place, I was languishing, dissipated and desperate yet again for something that felt real and familiar—and as a lifelong drinker, alcohol fit the bill. I was also doing my best to return home with at least something to report from an otherwise uneventful five-star sailing cruise, and, pathetic as it was, the little story about having found a bar in Manila with the exact same name as the place that Julie and I had moved to live next door to, back in Ann Arbor, seemed like some sort of meaningful triumph.

The well-groomed young server stood there politely with his hands clasped as my unconscious fought the same quiet war it had been for years, yet again remaining unacknowledged. I fingered a matchbook on the table in front of me and then looked back up at the waiter, a liar’s weak smile belying what I was about to say. “It’s just a cut,” I assured him. “Make me a tequila old fashioned—and use something good, wouldya?”

Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, one man's proof that despite what may seem like our inability to hear it, and all of our attempts to avoid it, we can all learn to listen to ourselves, and to act upon the inner voice of our self, our sanity and our soul.

Further reading

Here’s the table on contents for my memoir in progress. You might also enjoy some of my other writing on subjects mentioned here, such as:

or any of the other essays that you can find here:

I’ve got some questions for you

1. Have you ever injured yourself through sheer negligence? Do you bear any scars from self-indulgence and sloth?

2. What’s your own relationship with alcohol and how has that changed over time?

3. How do you know what’s right for you—and how has that changed?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

I didn’t start running until my forties. I could never see myself as one of those cringing, tense joggers frowning their awful, sad, tight runner’s frowns—the faces I would laugh at as I rolled by on my skateboard when I was just thirteen, thinking I’ll never be that guy, with my wheels going click-click—clack-clack over the cracks between the concrete sidewalk squares along the streets of San Francisco. I didn’t start until I was living in Potrero Hill with the second woman I proposed to and didn’t marry; she was a runner and helped to get me out the door for my first heaves around the neighborhood. As much as I dreaded the next mile, I could feel something coming alive, step by step—something building up in my legs and my chest that felt better than when I didn’t move.

I didn’t start thinking about running more until I ran across a copy of Born to Run on that boat trip in Chile. Chris McDougall’s great book helped me to understand how as humans, we are uniquely evolved to run, and that the idea that I’d held on to, that I wasn’t the ’running type,’ was just another way of avoiding doing what other people do, of giving myself a way to feel different—and a reason not to do anything.

Growing up the in the city, it’s no surprise that trail running didn’t really occur to me, and running on sidewalks and roads still holds no appeal, so I didn’t really start running regularly, or any distance, until I moved from the city across the Golden Gate bridge to Sausalito, where I could be closer to the trails in the headlands and on Mt. Tam.

It took me forty years to remember how much I love to run—and also to rediscover how my mind and body respond naturally to the terrain. Point me down a paved road and my legs will barely move, but the narrower the trail gets, the more I feel pulled ahead—and when faced with a stretch of winding singletrack, my eyes open, my feet get lighter, and I’m drawn forwards as if by a tractor beam, ready to race ahead, chasing the next patch of sun where it finds its way down through the trees to the fiddleheads, wild nettle and Indian paintbrush along the path.

I never became anything like a distance runner, not even really a serious runner, let alone a marathoner or an ultra guy, but by 2016 I’d gotten to the point beyond could, to where I was running six, seven and eight mile trail runs two or three times a week. I’m not claiming that running a few miles is anything exceptional, but I was really digging it, and it was making a difference.

Still, I wasn’t going out of my way to make things difficult for myself. Runners who claim to like hills must suffer from a lack of trauma. Not me—my favorite type of uphill is a gradual, rolling descent that lets me open up and really fly—and don’t have any problem knowing that I’m getting a little gravity assist. As a lifelong lover of maps, I use all the tools I can to find and design ideal running routes wherever I am, even right here at home. The loop that I ran most often in those years is a perfect seven in China Camp State Park that starts with an easy rolling two to warm up, then climbs steeply for a mile or so before offering a hero’s return for four miles of just-barely-downhill trail that winds through redwood, oak, and madrone forest along a ridge with views of San Pablo Bay.

I’d always thought of myself as an outdoorsperson, and largely thanks to my parents, I’d already become a competent sailor, skier, skateboarder, climber, and backpacker by the time I was in my teens. In my twenties I snowboarded, rode motorcycles and mountain bikes, and did a fair bit of windsurfing before I injured my back. In my thirties I climbed a lot indoors in the gym, did a bit of road cycling and even tried whitewater kayaking before beginning to get heavily into kitesurfing. In my forties, I also took up paragliding, and my passion for wind sports and flying took me all over the world, and even to become an adventure guide in and semi-pro athlete in Brazil.

I love all of those sports, and probably almost all of the others that I haven’t tried—and, all of them are all more complicated than running. As I learned when I did finally become a just-about-average and very middle-aged trail runner, running is the simplest and most effective dynamic, aerobic outdoor sport, and regardless of how much I love to do all sorts of other things—and all the complicated, colorful, and expensive gear involved—running delivers the biggest bang for my buck. All I need are a pair of shoes, shorts and a tee shirt, and I’m good, and the result can be just as meaningful, and even as dramatic, as what comes from sports that involve far more preparation, equipment—and risk.

One day that spring—the year after I’d sold my business—I was out on that same loop in China Camp that I’d returned to so many times. I’d already made the climb up from the lower section, and I was cruising back along one of my favorite parts of the trail higher up, feeling the ease, and fluidity—and power—that comes with moving fast in the outdoors.

The trail there is about two feet wide, just a little more than true singletrack, but still narrow enough that two runners coming from opposite directions have to step aside to let each other by. It was a perfect day for running; low sixties, clear, with a light breeze. The landscape had begun to dry out from one of our short California winters, but it was still early enough in the year that things hadn’t yet all gone to sun-baked dust.

My whole body felt light, and picking my way between rocks, roots, dips, and bumps of the trail felt more like floating—or flying. I was in good form, and proud of myself for being able to run like that at forty-six—at any age really, but especially since I hadn’t done much in the way of real exercise as a younger man.

I’d known that moving well feels good—really, really good—and I had experienced that quite a lot with all of the board- and wind-sports, climbing and hiking that I’d done, but it’s also true that I’d avoided things that felt hard. Running is simple and easy, but also nearly the most difficult in terms of how much energy it requires for a given distance, exceeded only by swimming. I’d been doing a lot of more complicated sports all my life that didn’t ask as much of my body in this very basic way, but I’d finally come around to the simple joy and pleasure of running—even if it is still hard to do.

Cruising along there, wide-eyed and exuberant, just enjoying myself in the outdoors, the sun filtered green and gold through the purple-skinned madrones as I rounded a bend to the right, a wide, shallow reach of water visible between the trees as the trail bent around the crown of a ridge before dipping back towards the shade. Having regained my wind after the steep climb, I was running well, head lifted, back straight, abs tight, breathing through my nose, my quads churning as I focused on the smaller muscles around my knees and ankles to keep the joints stable.

Just then, in the very next moment, as my feet continued to find their own way along, I found myself aware of my entire body as if from a short distance away, observing myself in slow motion. I watched myself move like water, each foot landing just where it needed to go—moving without conscious thought, but also not without thought at all.

Still as if from a point about six feet above and to the right, my mind’s eye snapped a single still frame as I was suspended in mid-stride, both feet in the air, my eyes forwards toward the stand of small redwoods in the next bend—and along with that freeze-frame image, a clear message appeared: “If my body can do that, then I can do that.”

My heart caught in my chest, and I pulled up right there in the middle of the trail. Tears streamed down my face as I heaved deep breaths of oxygenated air. After a minute of just breathing, I wiped away the tears and sweat, and my vision became crystalline-clear as I looked out across the water at the hills that framed the foot of the Napa Valley. It was precisely then that I realized how this thing often called “intuition” really works, at least for me—because that’s what I was doing as I moved along the trail. I was moving with awareness, but without thinking. I’d gotten a glimpse of myself responding to the terrain, not instinctively—intuitively. I could interject with conscious action as necessary, but for the most part there was no need to decide anything—certainly not the precise location of each footstep, which would of course be impossible anyhow, because the feet have already moved by the time the brain has registered the question of where to put them next.

For much of my life, when I went looking where I thought I’d find me, what I found instead was a hole that wouldn’t ever heal. I’d spent a lot of my twenties and thirties wondering not just “who am I?” but also “how could I not know?”—leaving me feeling like I’d missed out on what Ram Dass calls “somebody training.”It may well be that this was yet another rediscovery of the obvious, but as Maggie Nelson writes in On Freedom, there is a “fertile kinship between freedom and anxiety,” and, just as she did, “I had to learn it anew myself.”

As I leaned against an old wooden fence and took in a few more lungfuls of air, my heart rate moderating, I felt an electric wave of relief and elation surge through my entire body. I saw that just as I had come to trust my body to move down the trail without thinking about every single step, I could trust my self to just move more, in life. I saw how intuition could work for me, in my body. The old saying tells us to “trust your gut”—but that never really worked for me. It wasn’t in my gut—it was in my legs.

Running is an elemental practice in listening to where the body wants to go. We were all born to run, and when we do, the body has the chance to get out ahead of the conscious mind. We can’t think as fast as our feet, and so we get to watch and see where the body takes us. There’s a word for all of the low-level physical sensations of the inside of our bodies, the sore-stretch feeling of strength in the muscles, heavy-scratchy tiredness behind the eyes, the grey ache of the heart, the twisting pang of something not quite right in the belly. These are all forms of interoception—the “awareness of the inner state of our body”, and they all form the underlying foundation for what lies above, which is intuition—the result of our unconscious taking in the sensations in the body and, still without our conscious involvement, directing movement—which could be of body or mind—in response to that information.

Consciousness is not just a sport of the mind—full consciousness is a bodily function, and, as I’ve often heard said, the body is our “vehicle for the soul.” Even with all the time I’d spent prior to that day in so many different physical activities, I hadn’t made the connection between physical movement and having my full capacity available to navigate my own life with something other than agonizingly conscious decisions to guide me. After all that struggling with not knowing, here was the beginning of a real relationship with something that spoke clearly—and that gave direction—from a place that actually felt like it was part of me—inside. While it’s often said that insight arrives in moments of stillness, for me it happens much more often in moments of motion. I hadn’t thought much about “intuition” as this sort of inner voice at that point—other than in feeling that it was missing—but I’ve since come to see that intuition lies at the intersection of physical and psychological movement, and that it’s movement more than the awe at nature’s great temples that provokes the actual working and available aliveness of the senses. Surely, John Muir found inspiration in the scale and grandeur of Yosemite, just as Jacques Cousteau did in the depths, and Shackleton did in Antarctica, but my great appreciation for the infinite glory of the physical world, within and without, came along by way of a just-more-than-ordinary trail in suburban in Marin County, California.

That was where the alchemy happened, the transformation, the evolution from “fuck everything” to I’m in love with everything began. That is where I made the concrete connection between what had been an abstract idea of knowing myself and what seemed like a childish fantasy of “just” trusting that things would go well, and having a real sense of how to find my way—and my feet on the ground actually finding my way. In the middle lies the reality that just as the body with its senses will find its way to a good place, and in a good way—also, the mind, in our deep psyche, and in our emotional self, will tend towards finding a good way, a way of balance and trust and of truth, if we are taught and if we learn how to do so. We are not born with this ability fully intact. It must be nurtured, brought to light, and practiced. Otherwise, we will tend as I did towards confusion and bleak horizons, towards losing ourselves.

I straightened up, stretching my back and chest and legs and arms, feeling awake and alive, ready to move, and I remembered being in the woods back in Maine as a child. Little-boy me, jumping over fallen logs, dodging dangling ferns and buzzing bees, my small feet landing on rotting mushrooms and soft patches of bright-green moss, springing me back into the air, pushing me forward.

That child inside wakes up on trails like this. Another pulse of current jolted through my body, an awakening—of the child inside me, and also of my own full-grown self, an adult man, one and the same, reunited—and then I was gone like lightning, breathing hard, running free, flying through the trees.

Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, one man's proof that despite what may seem like our inability to hear it, and all of our attempts to avoid it, we can all learn to listen to ourselves, and to act upon the inner voice of our self, our sanity and our soul.

Further reading

• Born to Run by ‘barefoot runner’ Christopher McDougall

• Run or Die by ultra- and sky-runner Kilian Jornet

• Running Man by ultra-ultra-runner Charlie Engle

• On Freedom: Four Songs of Care and Constraint by Maggie Nelson

• What I Talk About When I Talk About Running by Haruki Murakami

• The Extended Mind: The Power of Thinking Outside the Brain by Annie Murphy Paul

• Polishing the Mirror: How to Live from Your Spiritual Heart by Ram Dass, as well as this video: Sacred in the Everyday.

• my podcast interview with Charlie Engle

• The film Running The Sahara, about Charlie’s epic mega-run across the Sahara

• My athlete profile on Strava

Here’s the table on contents for my memoir in progress. You might also enjoy some of my other writing on subjects mentioned here, such as:

or any of the other essays that you can find here:

I’ve got some questions for you

1. Are you a runner? How has the physical activity of running affected you, psychologically and emotionally?

2. What’s your own relationship with intuition and how has that changed over time?

3. What is your sense of self based on? Where does it live within you?

4. Where’s your favorite place to run?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

At nine am on the morning of March 5, 2015, I was standing outside the hangar of a small airstrip in Cloverdale, California, my few employees gathered around me. The hills were a lush spring green, and the day had begun clear and bright, the air still crisp but warming quickly in the sun. We all wore bulky maroon flight suits and four-point harnesses over our street clothes as we listened to the final words from the skydiving instructor. The briefing complete, we counted off in pairs, and two of us walked towards the plane for the first ride up. I could feel my phone in my pocket, and just then, before I climbed in, it vibrated silently with an alert.

I’d been waiting for an important message from my counter-party’s lead attorney, so as my right-hand man Rob and I paused and turned for a pre-flight photo, I pulled out my phone, opened my email, and with a few quick taps of my finger, made the last electronic signature that finalized the sale of my business. As the photographer’s shutter clicked away, the screen refreshed with a big green check mark. Gratified, elated, and excited to share the news—but not just yet—I folded myself through the door of the plane and settled in for the climb up to 12,000 feet.

Twelve minutes later, I was in free-fall. I’d started flying myself with paragliders the year before, and so I wasn’t totally unfamiliar with the feeling of being in the air, but skydiving is very different than free flight, and until that day, I hadn’t ever had the opportunity to jump out of a perfectly good airplane. It seemed like the perfect way to celebrate another successful conference—and the much bigger news that I’d soon be announcing to everyone else.

Here’s the thing though—even at 120mph, strapped to the front of a skydiving instructor, I was already thinking about the question that I knew would immediately follow my return to Earth.

I’d been working on selling the company for at least the past three years by this point, increasingly consumed with turning my little conference business into a well-oiled and well-documented machine—and I’d succeeded. Our events were more successful than ever, and at the same time I’d removed myself from daily operations enough that my acquirers had no problem with the fact that just two days later, I’d be disappearing over the horizon on another remote sailing trip, entirely off the grid and unreachable in the vast reaches between the remote atolls of the Marshall Islands.

The deal was done—and the ground was approaching rapidly. My pilot pulled the chute, and as he steered towards the landing, I readied myself for the question—and the related decision—that I anticipated with increasing anxiety. I knew that I as soon as we landed, or as soon as I told my staff that the sale was complete, and certainly as soon as I made that announcement more widely, I would be faced with the question of “what are you going to do now?”

This was the question I’d already been asked by some of the people that I’d been able to share the pending deal with. It was natural enough,and I understood their curiosity—but even thinking about the question made me grimace and shake my head, and I resented that I would be pressed for an answer, especially so soon after signing the contact.

Aside from skipping right past such an important moment, the question seemed to include the assumption that I somehow already had something else up my sleeve, as if I could have had the time or energy to figure out what that might be while I was doing everything had been required to get the company sold in the first place.

I certainly hadn’t.

After swooping back and forth a few times, we came in and flared for a gentle touchdown. The jump had been a rush, but the brief thrill ride was overshadowed by larger wheels turning in the background. I had just sold the business that I’d built myself, from scratch, over the past fifteen years! As much as I’d loved the experience of being an entrepreneur, I was overjoyed to have found a way to successfully hand the company over to an acquirer with a solid reputation—and, most of all, to be free of the whole thing myself. There’s more to tell at another time in the story of the business, but one thing that most folks don’t know or imagine about producing conferences as a business is that it’s like going back to play high-stakes poker, over and over again each time. You’re essentially “all in” with each event, and as soon as one is complete, you’re on to the next one. With a dozen or so major events each year, it’s a continuous cycle that is gratifying—and also exhausting and incredibly nerve-wracking.

Another problem with the impending question of what to do next was that much more than whatever I turned my attention to next, I was aching to finally have the opportunity to be someone other than the ‘conference guy’—so it wasn’t just that I had to figure out what to do. I had to figure out who I wanted to be—and how to become that person.

A good problem to have, sure, but now that I was back on the ground, this question was going to be impossible to avoid. My identity had been tied so tightly for so long to my business, and to being a business owner, that the logical next step would have been to start another business. I could see the possibility of that happening, and I certainly felt capable of it—but at a deeper level I felt exactly as Tim Krieder put it in I Wrote This Book Because I Love You: “We’ve all arrived at those moments when we look up from our lives and ask: Why am I this person I would rather not be? Where exactly did things go wrong?”

I gotta say, the “what next” question kindof just made me angry, because it poked at the truth beneath the surface. I had in many ways spent a lot of time being someone that I didn’t want to be—and that I still didn’t know who I did want to be. If I had known what next, then I would probably would have had a much better sense of what to do with myself in the first place, and I wouldn’t have ended up drifting into something so incredibly mundane—conferences, about advertising of all things—for so many long years.

Nevermind that I had actually had been able to dig myself out from that hole by doing what so few manage to do in selling the company—I still didn’t know myself well enough to know what to do next, and I could see how my perceived lack of direction could easily eclipse what I had only just accomplished.

Over the course of that morning, as the rest of my employees had their rides up to 12k and their free-fall back to the LZ, and then as we drove to the little wine-country town of Sonoma for a celebratory lunch, I began to realize just how much anxiety I had around decisions, and that I often found myself trying very hard to make a decision, feeling stuck, going back and forth, not knowing and frustrated to find myself facing, yet again, a version of the question that had vexed me since I was mid-teens: “who am I—and how could I not know?”

This might sound like nothing more than a very first-world problem that I should have perhaps considered myself fortunate enough to so-called suffer from, but I wasn’t so much tired of making decisions as I was tired of the feeling of not being able to make decisions, and this anxious cycle was part of my individual recipe for depression—trying to decide, and repeatedly re-experiencing that feeling of not knowing. The principle of neuropsychology that’s known as Hebb’s Law—“what fires together wires together”—describes how that by repeatedly traveling that path of not knowing, I was responding to, and then also reinforcing a pattern of thinking in which I was disconnected from myself, each repetition of which took me further away from any foundation of knowing, and also making it more likely that I ‘wouldn’t know’ again in the future.

I already knew that, somehow, I’d been practicing confusion for much of my life, and I’d always thought that the only way to unwind the knot of confusion was to think through a situation and decide. It became clear to me that morning that grinding away like this, trying to decide, often just resulted in a negative feedback loop of further confusion. I needed another way.

Setting myself the task of selling my business and achieving the result cemented a greater solidity and clarity in me. Over time, and also in the moments of the culminating result, I felt grounding effect of the accumulation of evidence that following the messages that I got from the deeper parts of my self did lead me in the right direction—when I managed to listen. It’s fair to say that I’d also earned a certain measure of freedom, not just by way of handing off the business to someone else, but because I’d earned some real money in the sale.

As we were seated in the restaurant for lunch, I got ready to tell the group what else I’d been up to while we were all jumping out of an plane that morning. By then, one thing I was clear on was that I wasn’t going to feel compelled to respond to anyone else’s question about my own future plans, and also that I wasn’t going to feel aimless or ashamed for not having an answer. I didn’t have an answer, but also, I wasn’t going to have “I don’t know” as my only answer, as had been the case so often in the past.

As with many other things along the way for me, the realization that I didn’t necessarily have to decide crystallized as one of those magic phrases that I’ve carried with me ever since.

The phrase that emerged: “Decide Nothing” would be my answer to “what next?”—and when those two words came together, they hit me in the chest with a flood of warm relief. Now, I’m certainly not the first person to get knocked upside the head with the idea that deciding might be not just a necessary pain in the ass but in fact just not really all that necessary. I’ve read Michael Singer’s The Surrender Experiment, as well as what Nassim Taleb sums up in Antifragile that “we are largely better at doing than we are at thinking,” but prior to getting this message myself, I hadn’t seen for myself the possibility of breaking out of the downward spiral of the endless decision loop.

Deciding can be exhausting, not much fun, and, very often, simply doesn’t work. There are plenty of folks who argue rather coherently that we don’t have much free will at all—that, as Sam Harris writes, “The intention to do one thing and not another does not originate in consciousness—rather, it appears in consciousness,” and so, no wonder that it causes us a lot of pain trying to insist on exercising our perhaps-imagined freedom to choose, or decide.

I had the chance to test out my brand-new axiom when I talked with an old friend the next morning. Just as I expected, he asked me exactly the question that I had been dreading—but that I was now ready for.

“So,” he said, “what are you going to do next, now that you’ve sold the business?”

“What’s next is I’m going exploring,” I replied. “And I’m not deciding anything for at least a year.”

From then onwards, and for quite some time, whenever I noticed the feeling of being stuck in decision-making, or even the feeling of a decision trying to get close to me, I would think of that phrase—“Decide Nothing”—and steer in the other direction. All of that feeling lost, anxious and confused, all of that spiraling down, leading me further and further into a desperate sense of no-self—those were symptoms that were trying to tell me that, by trying so hard to decide, and getting stuck there so often, I had ’let more important things remain unconscious.’ It was time to find out what those important things were, and I had to get comfortable with leaving space for that to emerge.

In just the following couple of years, I went on kitesurfing expeditions in the Marshall Islands, Micronesia, Brazil, Zanzibar, Cape Town, Maui, and the Philippines, upriver by ferry on the Amazon, paragliding in central Mexico, and trekking in the highlands of Tanzania and across the Lençóis Maranhenses, along with a lot of trail running right at home in the mountains of California. New friends in Brazil invited me to join them in making an adventure travel documentary, and to guide kitesurfing trips there—all of which I did while learning Brazilian Portuguese on the fly. Throughout this entire time I was also keeping up my commitment to the acquirer of the business I’d sold, and, in doing so, earned a million-dollar bonus payment that they delivered with their earnest congratulations.

All of this wasn’t ‘just travel,’ and of course I was at home quite a lot too, but I did find that I felt free in a new way to set off in whatever direction felt right, near or far, without much consideration to how or when I’d return. Sometimes I felt like going, and at other times I got the message to stay. I didn’t always read myself right, but I was learning to do so, and for me, movement is a big of how to do that, whether it’s the physical movement of outdoor sports or the larger-scale movement around the state, or the planet.

Instead of augering in on ”what next?,“ I’d begun to “eat the question”—to transform the question into a quest, not for the answer, but for what the question means. The answer, for the time being, turned out to be “nothing”—and doing that freed me to move away from who I had been, into the potential of who I could become—away from the black, and into the gold.

Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, one man's proof that despite what may seem like our inability to hear it, and all of our attempts to avoid it, we can all learn to listen to ourselves, and to act upon the inner voice of our self, our sanity and our soul.

Further reading

Tim Kreider, I Wrote This Book Because I Love You

Nassim Nicholas Taleb, Antifragile: Things That Gain From Disorder

Sam Harris, Free Will

Harry A. Wilmer, Practical Jung: Nuts and Bolts of Jungian Psychotherapy

Here’s the table on contents for my memoir in progress. You might also enjoy some of my other writing on subjects mentioned here, such as:

or any of the other essays that you can find here:

I’ve got some questions for you

1. Have you ever felt compelled to know what’s next, without knowing the answer?

2. What’s your own relationship with intuition and how has that changed over time?

3. How do you feel about decision-making?

4. Have you ever started, run, owned, or sold a business?

5. What’s a favorite story from your own life—especially one that you’re a little bit afraid to tell?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

By the time I had that daydream about my work being “sexy,” I was just about to give up on the whole thing. Much of the world was still feeling the effects of the so-called Global Financial Crisis of the late aughts. Time were tough for my little business too, and for a while there I was thinking about just walking away, but after ten years of hard work, I really wanted to have something to show for myself. Thanks in part to EO, I was coming to know an increasing number of other people who had managed to sell their own small companies, and so I began to see that that could at least be possible for me too.

Getting OPS off the ground with this new theme gave me some encouragement, and even though I had no idea of exactly how to get there, I decided to set myself the clear goal of selling the business. I didn’t know for sure whether or not I could actually get it done, or how long it would take, but from there on out, that was what I was aiming for.

Three things became clear. For one, I had to clean up my accounting, so I hired a real accounting firm to replace the stripper who’d been doing my bookkeeping on the side. Second, I had to start spreading the word that I was interested in selling, and trying to meet potential buyers. To that end, I started taking meetings with everyone I could find—but the thing that made the big difference in the end was coming across a conference that was in many ways much like my own, but instead of being about online advertising, it was about the business of conferences.

The most important, and least obvious thing was coming to understand that I needed to show that the business didn’t need me. If someone was going to buy the company, they’d most likely not want to take me along with it—I wouldn’t want to keep working on it anyhow—and in taking me out of the picture, they’d convert whatever I was paying myself as the owner into profit. This contradicted the conventional wisdom that as a business owner you need to be showing everyone how much time you’re putting in making a superhuman effort, but it made sense to me right away.

I began to offload work from myself to others, and to focus more and more of my energy on finding a possible buyer. It took some time, but by 2013 I’d found someone who was interested in buying the company—and who had the money. I’d cleaned things up, and the business was running well enough that I was able to start taking time off—which was exactly what they wanted to see—everything running smoothly, without the owner’s close involvement.

By the end of 2013, things were really heating up. I was getting into real negotiations with this potential acquirer, and at the same time I’d been elected as the next president of the San Francisco chapter of EO, a board position that I’d been working towards for some time.

I’d also just signed up for a five-year membership on my friend Gavin’s boat Discovery, which he had set up with a crew and an itinerary hitting some of the best—and most remote—kitesurfing spots in the entire world.

Just as the new year rolled around, I got a last-minute message from Gavin saying that he had a piece of communications equipment that he needed to get to the boat, which was currently in Chile. He offered up a spare crew berth for a ten day trip in the Chiloé Archipelago in exchange for someone to courier the package down to Puerto Montt, nearly two hours by air south of Santiago.

I didn’t take me more than thirty seconds to shoot him a quick reply saying, “I’m your guy,” and then I jumped on the computer see how I could get there. I had to be in Oahu by the 14^th of January for a meeting related to my upcoming board position with EO, but the boat was due to return to port the morning of the 13^th. If I made all my connections, I could fly from there to Santiago, Dallas, and San Francisco, swap my bags, and then onwards to Honolulu—and make it to the hotel there in time for dinner on the 14^th. Game on! I booked the flights.

Two days later, a large box arrived at my flat, just in time for me to jump in a cab to SFO. I checked it in along with my kite gear for the long haul down to Santiago, arriving early the morning of January 3. The whole thing had come together pretty quickly, and so it wasn’t until I walked off the plane in Santiago that I remembered that I’d have to go through customs coming into Chile—and that I didn’t even know exactly what was in that box.

There wasn’t much else to do. I just got in line, and when my turn came up, the friendly customs guy glanced at my bags and was about to wave me on…but then saw the conspicuously heavy-duty box roll down the conveyor towards me. Now I was starting to sweat. The box was at least two feet on a side, and still bearing the manufacturer’s markings,

“¿Es suyo?” Was it mine?

It sure was.

Looking at the box, and then back at me, the official asked, “¿Y esto, que es?”

“Equipo de comunicaciones,” I replied. “Usado. Por un barco.”

I was thinking that “used communications equipment” would be enough to get me through.

The customs official’s eyes twinkled.

He and another guy lifted the box up on the table there and sliced it open. As they went through the carefully-packed contents, I saw that it was a small system that provides an internet connection via satellite link, of the sort that’s often used on small yachts. Gavin’s boat was a deluxe operation, and some of the guests were used to being able to stay in touch at all times. My guess was that the existing system must have gone on the blink and needed replacement, stat, for one of the clients on the upcoming trip.

The equipment in the box looked expensive, and it certainly didn’t look “used.”

We had a bit more of a conversation, at the end of which the official explained very politely that I would have to pay something close to three thousand dollars in import duty unless, well, it wasn’t quite clear.

I couldn’t reach Gavin, nor the skipper on board Discovery, and so the box disappeared into the impound cage, and I was handed a little paper receipt.

The guy was just doing his job. In fact, they had been super cool with me and my makeshift Spanish, which was about sixty percent there, but also enough to tell that they weren’t trying to rip me off. In fact, it was one of those cases where, as has often been the case, I got along with random strangers in foreign languages better than Americans speaking English. It was an unfortunate situation, but everyone was in a good mood.

“OK amigos,” I said, “Yo vuelvo hasta poco”—“yo” still coming out pronounced as “sho” because I’d learned a lot of my Spanish from an Argentine who was living in Madrid.

I had the sense that the customs guy had hinted at what would get me out of the jam, but the language barrier and my own lack of preparedness left me mostly in the dark. Momentarily at loose ends, I went upstairs to find out how long I had before the last flight to Puerto Montt. I’d already missed the morning flight I had been scheduled to catch, but I could see that there were at least three more over the course of the day, and that the last one was at something like 5pm. I had several hours to solve the puzzle.

I went off to the side of the check-in hall and sat down on the floor, momentarily at loose ends. Gavin hadn’t given me any further details before leaving. Both of us were in a hurry, and I figured part of the deal was that he trusted me to sort it out—and I wanted to meet the challenge.

Sitting there staring at the white walls of Arturo Merino Benítez Airport, halfway around the world from anywhere, on my way to meet a boat I’d never been on and a bunch of people I’d never met, and stuck in customs limbo, help from outside didn’t seem to be forthcoming.

I was alone—and I was hungry. Leaving my bags were they lay for a few minutes, I grabbed a sandwich from a nearby counter, and sat back down to eat. Once I had something in my stomach, I went back to mulling over the problem. I could have been dejected, frustrated, and stressed but instead, I felt relaxed and confident that I would find a way to get that box out of customs though sheer force of will. What could have been problem became an opportunity.

The weight on my chest lifted, and I stood up and looked around, away from the main hall. I could see down a long white hallway full of administrative offices. I thought, maybe there’s something in here—and within a couple of minutes I came across a paper sign on one of the doors that said something about shipping and invoicing… aha! perhaps a freight forwarder? Another term I remembered from my mother’s work.

I knocked on the door, and, minor miracle, I heard someone stand up inside, and then open the door. Sure enough, it was some sort of shipping agency! Excited, I made my case as well as I could to the kind gentleman who’d opened up for me, and he was curious—and perhaps bored—enough to be willing to lend a hand.

At first it seemed like all he could do was confirm that I’d have to pay the duty to import the satellite gear, but over the course of the next few hours, I kept at it, insisting that there must be some other way. Although he hadn’t given me any guidance about how to get it through customs, the one thing Gavin had made clear was that he wasn’t going to pay to get this thing in the country.

“Es un barco de vela,” I said—a sailboat. The equipment was for the boat—and the boat wasn’t staying in Chile. “El barco no se queda en Chile.”

“Se va después de unas semanas.” I was trying to tell him that the boat was just passing through—that it was going to leave Chile, and I wasn’t really importing the equipment, because it would leave the country with the boat.

The shipping-office guy’s face lit up a bit. “¿El barco no se queda in Chile?” He was asking me to confirm that the boat wasn’t staying in Chile.

“Exactamente,” I said.

He squinted back at me.

“¿El barco… Es un yate?”

I felt my temperature rise. Now were were getting closer. It wasn’t just a “boat…”

“Claro que si! Un yate, preciso.”

He opened his eyes wide for emphasis, and said back to me something to the effect of, “why didn’t you tell me it was a yacht?”

Apparently, the subtle difference between a “boat” and a “yacht,” was very meaningful in this case, but I hadn’t known the Spanish word for yacht until that I’d learned it from him, right then.

“ok ok ok!” he said, very excited now. “Todo bien—es un yate in transito!”

And there were the magic words: Yacht in transit.

Now, as my new friend explained, I just had to prove it to customs.

After another hour or two hanging out with Miguel Yanez in his little office, doing my best to stay cool, I finally managed to get ahold of the captain, who had been running around doing last-minute provisioning. Once he understood what I needed, within half an hour a fax rolled off of Miguel’s machine. I piled my surfboard and kite bags back on a trolley and rolled back down to the customs office again, feeling triumphant. I was relieved to see that my guy from the morning shift was still there. He waved and smiled a happy welcome, asking me if I had any news.

“¿Hay noticias?“

The words came tumbling out of my mouth. “Es un yate in transito, amigo! Yate in transito! Perfecto, no?”

I handed him the sheet of paper. He gave it a once-over, and then, looked up, smiled, and nodded. He’d been on my side from the start, but I had to solve the riddle myself—and I did, all in a foreign language, and thanks to a sense of confidence that was still settling into my bones. It certainly wasn’t a life-or-death situation, but this small victory—and the fact that I’d ended up there in the first place, and was about to embark upon a once-in-a-lifetime bit of adventure sailing—felt like a real validation.

The friendly official reached for one of his stamps, inked it up, and ka-chunk—I was cleared! The whole crew was there watching, and they laughed and clapped for me as they retrieved my box and lifted it back up onto the stainless-steel customs desk.

An hour later, the sun was already low over the Pacific, casting a golden light on the conical volcanic peak of Villarrica as I flew south to meet the boat in Puerto Montt. I’ll never forget how I felt on that plane. It wasn’t just the accomplishment of solving the problem, but the warm glow that came from following the voice within. I was finally starting to feel like I was making the right moves for me.

Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, one man's proof that despite what may seem like our inability to hear it, and all of our attempts to avoid it, we can all learn to listen to ourselves, and to act upon the inner voice of our self, our sanity and our soul.

Further reading

Here’s the table on contents for my memoir in progress. You might also enjoy some of my other work, such as:

or any of the other essays that you can find here:

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

Not all that long after crashing my car, I experienced another, very different sort of collision in my world as a new creative energy came to the fore—and as so often in the past, it was by way of another girlfriend. This time the result wasn’t a disaster but an epiphany, followed by a life-changing success.

Kat was an artist that I’d met in a roundabout way through my conference business; we were planning to hold one of our events in New Orleans, and she had set up shop there in the wake of Hurricane Katrina, buying several ruined properties on a shot-out block in the Lower Eighth, and heading up a loose collective of artists and musicians whose mission—described with a mischievous wink—was “life is art.” A platinum blonde with an otherworldly look, space-blue eyes and unshakable poise, Kat had grown up at the cultural intersection of California aerospace skunkworks and early psychedelic intelligentsia, and we developed a relationship as we shuttled between San Francisco, New Orleans, New York and Europe that was romantic at times, but first of all, creative and economic.

I’d once been called a snob for admitting that I wanted more artists as friends; the fact was and still is that I admire the freely creative more than anything else, and Kat was a force of that kind of nature, born free and actually living a life that was so far from what I knew that I couldn’t really begin to imagine it—and so, it’s true that that was a big part of what attracted me to her world. It’s also true that, as she saw things, the entire purpose of money was for the making of art, and so she was unabashed in her pursuit and consumption of funding, however it might be secured—and her personal relationships often had a financial component, as did our own. While I was certainly familiar with the traditional masculine role of covering dinner, plane tickets, and even the rent, it was a bit of a leap for me to digest her requests for five- and ten-thousand dollar checks to back her creative projects.

I eventually saw her logic. Her argument was: you seem to have extra money, I can use it, so why not slide some my way? She didn’t hesitate to play the coquette in making her pitch, and I did write some checks, which, along with the fact that we were intimate with one another, and had also in certain respects become business partners, made for a complicated relationship indeed.

Kat was not just some gallery girl. She’d trained as an architect, and had real skills in getting things done, as well as an incredibly powerful charisma that always attracted volunteers of all sorts. Men and women both were constantly turning up at her door ready to do her bidding, and often with no expectation of pay. They just wanted to be around her—just as I did, and I suspect that I wasn’t the only one paying for privilege, one way or another. I suppose there was a sliding scale.

She’d made a bit of a name for herself around town post-Katrina, enough to open doors beyond the art-school world that came through to gawk at her ramshackle installations. When word got around that a group of young club promoters were aiming to open a sort of members-only lounge on St. Charles Avenue in a unlikely historic structure that had been reconstructed from parts salvaged from the Eiffel Tower in Paris, she angled hard for the gig—and, after a few meetings during which we cooked up an entirely imaginary budget and agreed to an equally unlikely contract—she landed it.

Her clients thought they were getting an art director, project manager, and draftsperson all rolled into one; she giggled and assured them of her chops—but she saw the whole thing as a performance. They had a budget, a schedule, and the full intention of opening a banging new venue. To her, it was yet another opportunity to transform their geld into… pretty much whatever came to her pretty little mind.

They handed over their blueprints, and she pulled out her little black book. A couple of weeks later, a pack of her most talented acolytes descended in response to the lure of paid work—not that she’d necessarily promised anything specific. As more and more of these wild-haired, powerful young women arrived, it became clear that the brick shell of a bakery where she lived was too bare, and too edgy, to accommodate them all. The solution, of course, was to move the whole lot of them to the job site!

It’s fair to say that the clients and investors were at least momentarily taken aback to find her living there, but this is the kind of thing that can happen nowhere else but New Orleans—especially in the years following the storm. And after all, how else was this ragtag team to discern the subtle energies of the place well enough to determine what needed doing?

Visiting between my own business trips for my ongoing series of conferences, I arrived again at one point after they had been occupying the place for some weeks. Occupying a quarter of a city block, the building is an octagonal structure of steel and glass forming a single interior space more than a hundred feet across and thirty feet high, all suspended fifteen feet or so above the ground. It looked strange sitting among the gingerbreaded antebellum mansions of the surrounding Garden district. Like the original Tower in Paris, it might have seemed futuristic at the time of its original construction in the late 1800’s, but at this point the building had the appearance of an ungainly iron-age spaceship that had suffered a mechanical failure on the launch pad and now sat idle. The paint was peeling, and rust streaked down the pilings into the sticky, disused asphalt parking lot below.

Kat and six or seven of her friends were sleeping and working there, sharing a single rundown bathroom and a heavily-used industrial kitchen. There were no bathing facilities, and the AC came and went with the summer storms. I pitched in however I could, bringing in cases of wine, cooking big, cheap dinners out of whatever was on hand, and, after weeks of makeshift showers with a garden hose in the parking lot, digging an old bathtub out of Kat’s garden and plumbing it, at her request, smack in the middle of the space that we all shared. The women studied Jung’s Red Book, organized photo shoots and hammered away at various projects what were curious and sometimes beautiful, but also mostly of no practical use in the context of a functioning restaurant.

The heat did its best to steam us all into submission and sloth, but we weren’t slacking. We we working hard to finish something that could at least be claimed to meet the terms of the contact that Kat had signed—and, it was all part of the performance, which they all took even more seriously.

One morning as we rushed to meet the deadline for an early-opening party, the atmosphere was crackling with the accumulated tension of all of us living there together in a pile. By ten o’clock the air inside what was effectively a giant Victorian hothouse had already crossed a threshold that we knew well. We’d be sweating until well after dark, and the space was a clamor of visiting workers, sawdust, the hum and chatter of power tools, and a dozen simultaneous conversations, the angled panes reflecting blinding arcs of sunlight in every direction. I was weary from the night before, the heat—and also of my peculiar status.

Kat was the queen of the whole show, which gave me a certain cachet as her man, but I was alone amidst a coven of whispering, sensual women who knew that I was partially underwriting their experiment. Did that grant me more power, or less? To me, it felt like less, as if I was the client, as opposed to the patron.

What’s more, by that point, Kat and I weren’t having sex. We were still sharing a bed, but the relationship had shifted. I was there to support her project, but also because I knew that I was learning something important. My position had become a combination of favored concubine, eunuch assistant, and student assistant. It was emasculating, unsatisfying and unsustainable, but it was also a fascinating, dynamic and very unique environment, and I knew that it was a moment for me that wouldn’t be repeated.

Later that morning, as the sun neared its blazing noontime zenith, I searched the space for somewhere quiet and cool to rest. I found refuge in what one of her collaborators called the Superconductor, described as an “orgone accumulator” in the form of a large tent framed in chicken wire and covered in a thousand bolts of florid silk. I took the pseudo-science of this so-called orgone energy as yet another conceptual reference; either way, it made a perfect spot for a nap.

I ducked through one of the openings in the fabric and crawled deep inside, finding myself in a womb-like cavern suffused with a soft glow filtering through the layers of colorful cloth. The insistent din of activity receded as I stretched out, cocooned, and fell quickly into dreaming.

As the only man chosen—or who had dared—to join their all-female tribe, I had been keenly aware of the sexual energy in the room, day after day—and that all of that energy was subsumed into the creative vortex. Art took precedence over everything. Perhaps I was oblivious, but it seemed to me that sex was everywhere but the physical act; instead, erotic energy was bunkered by night and then burned as psychosexual fuel in the daytime—and now, I was asleep inside a homebuilt orgasmatron.

I lay on my back, suffused in a honeyed warmth that I hadn’t felt in weeks. No wonder my unconscious mind drifted from its usual dreamtime patterns of hurried pursuit and attempts at escape to an expansive vision of orgiastic pleasure, populated by the same group of comely witches that I was living and working with.

After an hour, I woke with a snap—fully awake, wholly refreshed, and with no tension whatsoever in my body. Everything had drained away—except for a curious phrase which scrolled clearly across my interior visual field in the last moments before I rose: “OPS is sexy.”

I couldn’t help but laugh. I’d followed yet another woman—and for once, not on an alcohol and sex-fueled bender but in response to my creative intuition—this time to New Orleans, becoming part of her brilliantly zany, Warholian ’factory,’ and then finally climbed right up into the birthing chamber itself, where all of the repressed sexual energy had been alchemized, reduced, and spat out again—as nothing more or less than the word “sex” itself.

Sex was in the air, but nobody was having sex. The whole thing was already a sort of cosmic joke, all the more for the fact that nobody but me would have understood what “OPS” was, and that of course it was the farthest thing from “sexy,” or even just something other than unknown and forgettable.

OPS was the name I’d come up with for a new event that I was planning to introduce as an adjunct to my original AdMonsters conferences, in an effort for further expand my business. Short for “operations,” or really, online advertising operations, I’m sure that this incredibly obscure niche within the world of digital media—or, for that matter, any conference at all—had ever occurred to anyone as anything like alluring.

Perhaps though, as my dream was suggesting, the opposite could somehow also be true.

The fact was that at the time, almost every web site from the New York Times to Google depended on advertising for almost all of their income, and because of the unbelievably byzantine, multi-layered software systems that were required to run these sites, no money could be made without the constant efforts of these almost always anonymous ops teams.

That was true—but the truth is rarely enough to get anyone excited. After ten years of serving this core audience as a tribe unto themselves, I’d already determined that it was time to bring them out into the light, but I hadn’t been clear on how to transform the public perception of “ops.“

The orgone tent had just dreamed me up the perfect solution. Just by invoking the word, it became clear that these nerds in the basement could be seen as pretty damn sexy after all. In actuality, they were not just central but essential, and without them the machinery of the entire online media landscape would grind to a halt. As ridiculous as it sounded, “OPS” was sexy—and in part, just because I had dreamed it.

Later that summer, I hired one of Kat’s entourage to fabricate a mirrored podium with a dramatically glowing bright-blue neon OPS sign to on stage, and kicked off the first of these new conferences with an awkward but heartfelt skit explaining what had come to me in my dream. It may have been laughable—but you know what, it worked. The new conference was a success—and, just as importantly, the idea that their work was sexier than anyone had thought took off, and the roles of not just ad ops, but all kinds of “ops” are now seen as a crucial part of the landscape of how digital companies do their business.

Those words had a real impact. I’d conjured up my own little spell—and although in the large scheme of things, the idea that this ops thing is anything like cool is still a hard sell, it’s also true that ten years down the road, some people in that industry were still using the phrase “ops is sexy”—and along with what it did to open the doors on that little world, that simple message did a lot to point me and my business in the direction of a truly life-changing milestone that I achieved not all that long afterwards.

That momentary revelation was concrete evidence that my own creative energy was coming to the surface, into my daily life, and even into my own business. Much like the attendees at my conferences, I began to see that the work that I’d been so alienated from for so long could exciting, stimulating, worth putting my heart into, and even something to be proud of.

An orgone-infused daydream helped to make my work alive for me again—and it helped to make me alive again. Something really had rubbed off, and I would never be the same because of it.

Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, one man's proof that despite what may seem like our inability to hear it, and all of our attempts to avoid it, we can all learn to listen to ourselves, and to act upon the inner voice of our self, our sanity and our soul.

Further reading

Here’s the table on contents for the memoir. You might also enjoy some of my other work, such as:

or any of the other essays that you can find here:

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

When I was growing up, Ocean Beach wore a permanent shroud of blowing grey fog. I only remember going there at night to crouch around a fire of splintered pallets and pull off a bottle of Old Crow—never in the daytime. There’s way less fog these days, and the sun is no longer a stranger to the far west side of San Francisco. Only a few hard men went out to surf in the old days, but now it’s a playground, and when the wind blows, the surfers are replaced by those of us who use kites to pull ourselves into the waves.

The change in the weather has made it far more attractive, but OB still demands respect. Swells roll straight in from thousands of miles of open ocean onto sandbars that shift constantly with the strong currents pushing in and out of the bay, and a couple of hours in the water there felt like a battle—one that I chose, but that still always carried a threat.

One summer evening back in the heart of my kitesurfing years, I hauled myself out of the water there, drained, almost stumbling from the cold and exertion—and euphoric, suffused with the electric glimmer of having kept myself alive in the elements. As I stripped off my wetsuit, I could already feel the pull from the bar at the Chalet, right across the Great Highway. In those days I always wanted a beer after being in the ocean, not just to slake my thirst, but to bring myself back down to earth after the thrashing myself in the double-overhead surf and twenty-five mile-an-hour wind. I wanted soothing, and shelter, and something to swallow that wasn’t salt water—and I needed to keep the ball rolling, from one kind of stimulation to the next.

I ran into a few friends at the bar, and after an hour or so, three pints plus a shot of tequila had made for the perfect amateur athlete’s speedball. Adrenaline and alcohol, probably the oldest one-two there is, and I was awash in what felt like the thrill of victory; free to be right there on that Tuesday afternoon, wind-blown and salt-crusted, buzzing with aliveness and surrounded by my friends and fellow watermen.

Some had families; not me, but still, I knew when to call it. We were celebrating, not drowning ourselves, and I stopped short of a full heat-on, for sure. A couple of minutes later I was cruising up Fulton Street away from the beach, my toes still half numb from the ocean, enjoying the heat coming through from the driver’s seat onto my back, happy as I’d ever been.

Happy—but not content. I was carrying too much energy to just go home and sit there alone. I thought for a minute, fumbling with the tangle of cables in the center console and steering with my knee until I got the headset plugged into my phone, as it occurred to me to share some of my newfound lust for life with my old Thursday night drinking partner. I often wished that my phone would ring more often, and I thought, well, maybe he’s thinking the same thing. I think of this now as if you want something, give it away—and at the moment, I thought just call—and so I did.

As I listened to his phone ring, I had my eyes on the vehicles packed in one after another along the edge of Golden Gate park to my right: several cars, a converted short bus, two more cars, and pickup, another car, and then a white van.

My friend picked up. While I was used to oscillating between excitement and flat-out funk, as long as I’d known him, this guy was almost always in neutral at best, and—no surprise—his overall mood hadn’t improved with a decade as a defense lawyer. I was casually repeating the same suggestion on him that I’d made several times in the past—that shifting his skills into a private-eye operation might well make for a less dreary day-to-day, and he was nonplussed yet again, as I rolled up on the white van, 15 over the limit, hugging the left side of the lane.

Fulton is two lanes each direction through there, but it shouldn’t be. It’s narrow, with no separation between the traffic going either direction, and packed with parked cars on both sides. It was clear that plenty hadn’t moved for some time; people were living right there, half in traffic, half in the juniper woods growing the old dunes.

I don’t know whether I would have blown over, but there was no doubt that I’d had a few drinks, and I was salt-water drowsy on top of that. My reflexes certainly weren’t tip top.

I was running the gauntlet, and I almost made it. Almost.

Just as I was cruising by the white van, the door swung wide open, jutting out in front my car.

My lawyer friend heard the whole thing over the phone—the sound of metal on metal, exploding safety glass, and then me, yelling “Mother–fucker! Fuck! Fuck!” but he was imperturbable as always, super dry, and so all I got back was, “um, what happened?”

I was in some minor shock—still rolling up the boulevard, and I hadn’t slowed down. My heart was hammering as I looked right and left, trying to assess the damage.

There was a pile of shattered auto glass in the passenger seat, and more in my lap. The right side mirror was dangling off its mount.

“This fucking van!” I said. “The guy threw his door open right in front of me! I swerved, but not fast enough. I got glass all over me. Motherfucker!”

“Was there a person? Did you hit someone?”

I hadn’t seen anyone; I just figured there was a guy in the van.

“No. I didn’t even see an arm—just the door swinging out,” I said.

There was silence on the other end of the line as I brushed glass onto the floor. I was already in an awkward position at best, at least four blocks away from where I’d hit the van, and I still hadn’t stopped. I glanced in the rear-view; nobody was behind me. Maybe nobody had even seen what had happened.

I don’t know if I would’ve blown over, but I didn’t have time to stop to think, and I didn’t think about stopping. It wasn’t that I didn’t want to deal with the consequences; I grew up avoiding the police, and it was automatic. I wasn’t getting done for a DUI—not me. I kept going.

Only a few seconds had passed when my friend spoke up with the critical question.

“Did you stop?” he asked.

“No,” I said—and it was too late to turn around. I knew I had to run.

“I turned into the park on Eighth. I don’t think anyone saw me.”

Now the guy-who-wasn’t-a-PI spoke with more energy. “Drive home,” he said, the words coming clear and quick. “Use back streets. Put the car in the garage, and take it in tomorrow—not your regular body shop. Pay cash.”

“OK. Thanks man. Sorry. Later.”

We hung up, and I yanked the headset out of my ears. I was in a half panic, expecting that I might get pulled over any second, forced to clear action by the feeling that I had no alternative but to go through with the path I’d unconsciously chosen.

I knew the slow way home—wind through the park, over 17^th and then down through the Mission. I didn’t know what the car looked like, but it was already getting dark, and I just tried to play it cool, even though I’m sure my pulse was in the 180’s as I worked my way across the city.

I didn’t know until I pulled into my garage that the impact with the door of the white van had pretty much peeled off the right side of my car. The passenger door was intact, but the two rear body panels on that side were entirely gone—sheared off and left in a pile of parts on the street.

I took my time getting rid of the broken glass with my neighbor’s Shop-Vac, wondering the whole time if somehow my vehicle could be traced. Of course the body panels could be identified, but for some reason I felt confident that something I had in common with whoever was living in his white van along the park there was that neither of us wanted the police up in our business.

Somehow I managed to get to sleep. First thing in the morning I dashed around the corner to a no-name body shop and asked them to patch things up, off the books. They took my cash, no questions asked, and two days later the car was good as new.

I got away with it. Another narrow escape, and I knew it damn well.

Of course I knew what would have been the right thing to do. Stop the car. Turn around. Go back and see what had actually happened. Call the police, wait for them to show up.

None of those things even came to mind as I drove away from the scene.

Somehow, I found myself as someone who’d done a hit and run—and suddenly I could see how a split-second move, an unconscious, selfish impulse could result in real disaster. I was still nowhere near making any major changes in my own life, but I could see that this crash was a message, much like the anxiety attack, or whatever it was, that I’d had in my kitchen a couple of years before.

I didn’t know exactly what the deeper message was—but one thing I was sure of was that I didn’t want either of those things to ever happen again, and one was easy enough to be sure of. I’d been drinking and driving since I had started driving, and I’d always gotten away with it, even though I knew that couldn’t last. It didn’t occur to me to stop drinking, but after my own little taste of true crime that afternoon, I did stop drinking and driving.

Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, one man's proof that despite what may seem like our inability to hear it, and all of our attempts to avoid it, we can all learn to listen to ourselves, and to act upon the inner voice of our self, our sanity and our soul.

Further reading

Here’s the table on contents for the memoir. You might also enjoy some of my other work, such as:

or any of the other essays that you can find here:

What does this bring up for you?

1. Ever felt like you got away with something? Like you deserved to get away with something?

2. What did you learn from that experience?

3. What’s your own relationship with adrenaline? with alcohol? How are they inter-related?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

I did most of my air travel in the days when you still got a paper stub for your boarding pass. I was always on a plane. Minneapolis, New York, Boston, Amsterdam, Cabo, Montreal, Boulder, Portland, and New Orleans, London, Milan, Lisbon, Madrid, and New York, always New York City. It did sometimes occur to me to save them but, man, if you don’t save them all, what’s the point, right?—and so, one by one, they went in the can, but I sure do wish I’d collected all of those little fuckers. There would have been hundreds, and if I had hung on to them, no doubt they’d help me remember something more from all those trips.

When I do scan for memories, the first thing that sticks out is that leaving was always hard. Especially if I was alone, packing for a trip often brought me to tears, feeling crushed by a loneliness that came to a head as I put socks and underwear into a bag yet again, no-one to say goodbye to, nobody at the other end. The sadness would pass as soon as I left the house though, and in the cab to the airport I’d be back in my groove, relaxed and excited, cruising to the gate, and then that delicious rush of the plane’s engines pushing me back in my seat.

It had always been true that the only things that really relaxed me were sex, exercise and alcohol or other escapes like travel—I was getting far too little of the second and way too much of the third. I’d always had a strong feeling for the shape of the world, and so no wonder I loved to jet off so often, but the truth was that I was dying to get back outside more, to get my hands and feet on the earth, to feel the wind and the sun, to grapple with things—not just stare out the window of a jet at thirty-eight thousand feet.

As good as my own conferences were as conferences, they were still…just conferences—and they were still about…fucking advertising…hard to fucking believe, but I was learning to live with it—and I was bored stiff sitting in a windowless meeting room doing my part to keep things interesting for the participants, mostly looking forward to hitting the bar. One thing I did do with the conferences was to set aside a half day of the three-plus day agenda for outdoor activities. We’d book a local guide to lead everyone hiking, cycling, rafting, climbing, or sailing—whatever made sense, depending on where we were.

Rock climbing, sailing and backpacking had been in my blood at a young age, and I still felt at home in the mountains and on the water, but all those years of city living meant that I had a lot more actual experience in bars and restaurants than I did out in the blue and green. My love of the outdoors was trying to come back to the surface, and these little bits of planned group activity were my way of remembering what I could, at the time, and sharing it with others.

When I wasn’t on the road with my conferences, I was at home in San Francisco, and kitesurfing was becoming more and more of a passion for me. Many more doors would open for me by way of adventure sports in the years to come, but it was kiting that really got me out in the world again. Every outdoor sport has its own sweet spot in terms of geographic and climatic conditions, and as you get into whatever it is you’re into, you tend to start scanning the globe—or Google Maps—for places that seem like they would be ideal. Just as divers look for reefs and wrecks and trail runners scout for singletrack, kiters look for warm water, strong wind, and waves—and on the northern coast of Brazil there is a stretch of coast that runs for more than a thousand miles, perfectly aligned with the north-east Atlantic trades and lined the entire way with soft, golden sand, tropical river mouths, and humble fishing villages, a few of which have grown into well-known destinations for wind-sports enthusiasts over the years.

I’d made a few sailing trips to places like Baja, Sardinia, and Venezuela back when I was windsurfing, but I didn’t hear about Brazil until I became a regular at Crissy Field, right in my home town. Summer is the heart of the sailing season here, and it’s widely known that’s summer isn’t the warmest or sunniest time of the year in San Francisco. After coming off the water we’d all gather in the grassy parking area, dripping with cold salt water and shivering in the fog, and talk about places we could go where we wouldn’t have to wear a wetsuit.

One magic name kept coming up—Jericoacoara, ”Jeri” for short. Nothing to do with the ancient city of Jericho, but that didn’t prevent the alliteration from adding to its mystique. Jeri really is in the middle of nowhere, a tiny little beach town four or five hours drive from the nearest airport, its streets just unpaved paths of beach sand, and in the sailing season the wind blew hard day and night. After hearing that name whispered however many hundred times, and since I’d already earned my stripes in the expert-level sailing conditions on the Bay, I was ready for a trip to Jeri at the end of my first full year as a kitesurfer.

That first time I went to Brazil hit me in the best possible way. Kitesurfing isn’t a sport that’s going to get you in shape all by itself, but it had already gotten me feeling more alive than I had been in years, and now I was out exploring with a purpose, with people who were there for the love of the sport—and in the kind of place that’s remote enough to be proud of, just for having gotten there.

I usually did my best to avoid the subject, but one day on the beach in some even smaller fish camp to the east of Jeri, I got to talking with another American kiter guy about business. My conferences were doing better than ever, but I was feeling more and more disconnected from what I’d created—the people who showed up at the conferences were all there to meet each other, not me, and I was feeling alone yet again, even though I’d created the whole thing myself, and, needless to say, putting on conferences is a lot like throwing parties for a living—so I should have been having a lot more fun.

Pretty common situation really, as entrepreneurs often end up creating a product to serve some need that they had in a previous career, and then shift to creating that product instead of doing whatever it was they were doing before, leaving behind their former peers in the process. As we wound down from a long day on the water, my new friend David told me about a group that sounded like my own conference in a lot of ways—a network of professional peers organized around the principles of community, mutual support, and growth—except that it was for small business owners instead of people who worked in online publishing and advertising. There’s that word again.

Like most self-taught entrepreneurs, I’d been so deep into getting my business up and running that it had never crossed my mind that something like what I had put so much energy into creating for others might exist for myself—but one thing I had learned after what were already several years in the conference business, was that in fact there was a conference for just about everything.

A few weeks later back in San Francisco, David invited me to a meeting of this slightly mysterious group that he referred to as “EO”, and while I didn’t really recognize anyone there as my kind of people, in a way that was reassuring because one thing that was very clear to me was that I didn’t know anyone else at that point in my life who had started a business on their own. I did know a few tech entrepreneurs who had raised VC money to fund their software “startup” dreams, but nobody like me who had actually started something from scratch, and had gotten to the point where it was something of a success. I was looking for something different from what I already knew, not for more of the same—and for once, I was actually looking to join something instead of just doing it myself. Although I’d only just begun to realize this, it was starting to become clear to me that I’d spent most of my life saying “no” to just about everything, especially to groups led by other people, and that if I insisted on rejecting everything, that I wouldn’t ever have the opportunity to learn anything from anyone else.

Within a year of joining EO, I found myself part of a global community of more than ten thousand small business owners, all very different but all sharing a key set of common experiences, and all with businesses making at least $1M a year in revenue—still tiny by most standards, but big enough to mean these weren’t just solo operators. Along with the kitesurfing community that I was by then a real part of, I’d found new and solid ground in EO, and I remained a member of that group for most of the ten years to come, and the support that I got from being part of that organization played a huge part in the increasing success of my own business, and, in fact, in my own personal growth.

I was learning how join up. I was learning how to be part of something—and I was learning, little by little, how to listen to myself, and how good it felt when something did bubble up from inside, and when I had the presence of mind to follow that voice, instead of being stuck in “in don’t know.” The terrifying panic attack that I’d had not so long ago had left a powerful impression on me, but the bright flashes of those sickening and dangerous images came less and less frequently as I began to move more to my own rhythm in the world. For the most part I was still unaware that I was changing my patterns—it hadn’t surfaced, or gone deep enough yet, but I was changing, even though it was also true that I was very much still trying to figure out more of just who I was.

I was still conflicted about everything. Most of all I wanted freedom, and I loved when my business started doing well enough for a lineup of heavy checks to show up in the mail on a regular basis, and that on average I only had to work about half time, but I still hated that the whole thing was about advertising, and that aside from that all-too-familiar subject matter, the business itself was so obscure that it always took at least fifteen minutes to explain to anyone exactly how producing conferences amounted to a business at all. Most people just didn’t get it. I was tired of explaining, and although it was very much my own creation, I had a hard time drawing a through line from any of my deeper interests to the company that I was putting so much energy into.

I thought—or at least I had thought—that I wanted to get married and start a family, but clearly, I didn’t really want that enough make anything like a clear, honest, or intentional move towards that kind of future. I wanted more connection, and I was becoming more aware of at least some of my patterns, in particular how I kept seeking out disconnected, edgy sex, and at the same time getting over-attached to whoever I happened to be seeing at the time—but I still didn’t get why nothing seemed to stick very long.

I wanted to feel less depressed—and I still wanted someone else figure out how to do that for me. I wanted to feel healthier and more fit, but I was still out of shape, overweight, and suffering from chronic weakness and pain in my back. Back and forth between my flat in San Francisco, terminal three at SFO, and wherever that time tunnel took me, I zigged and zagged a jagged and often haggard—but less insane edge. JFK, Frankfurt, São Paolo, Sydney—they were not all the same, not at all, and I had a place to come back to—but my memories of all these very different places blur together, and what remains clear was that I still wasn’t all that sure about what I wanted.

I still felt like I lacked a foundation. Identity was a concept with no ground. Like so many others explorers I suppose, I was looking for the edge without knowing where or why, going away from the empty known more than toward anything else in particular, just looking, no, “no, thanks,” I’d said, “just looking,” just looking for something to light me up, something to pull me along, something to call my own, something that felt like me. At least when I was at home, I was still going to therapy two or three times a week, and my fear—or my chief complaint—was that I didn’t know why I didn’t know more about myself, about who “I” was. I was making progress, but I still didn’t feel solid. I felt like my name led to a list of places. There had to be a person there—but who was he?

Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, the book-length memoir about a man learning to listen to himself, and the price I paid until I learned how to do that, serialized right here on Substack with a new chapter published every week.

You can find everything from the memoir that I’ve published so far right here.

DECIDE NOTHING is a reader-supported publication. To receive new posts and support my work, please consider becoming a free or paid subscriber.

Further reading

Here’s the table on contents for the memoir. You might also enjoy some of my other work, such as

or any of the other essays that you can find here

What does this bring up for you?

1. Have you ever started a business of your own?

2. What’s your experience with the endless fascination of travel?

3. What’s your experience with joining groups versus doing things on your own?

4. Where is the foundation of your own identity?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

Much as with depression, I never used to really get what people meant by anxiety. In retrospect, I felt both of these things a lot, but at the time I didn’t feel that my own experience connected to those terms, in large part because I didn’t want to identify with some sort of general condition. I still don’t. I don’t say that I “had depression,” or that I “am anxious,” but that I felt depressed, or that I feel anxious. Why would I want to identify myself semi-permanently with what should be a transitory psychological state? I still think that’s right, although for a long time it also served keep me at a distance from what was often my actual experience of recurring depression and acute anxiety.

By the middle of 2006 it had been more than a year since I split with Jenna, and just two years since I dropped out of grad school and returned to San Francisco. I was living alone again, working away at my now just-more-than-nascent business, scrambling between dates and girlfriends, and although I had started to take better care of myself in some basic ways, things were still very much getting worse for me on the inside. Thanks to my friend Peter, I did start seeing a therapist—and was soon seeing her two or even three times as week—but again, nobody explained how it was supposed to work, and I was too naïve and needful to think of asking. I just showed up, usually feeling desperate and alone, and left feeling a bit less desperate, still alone, went about my business for a day or two, and then found my way back to her office again. All of that inner work did eventually make a huge impact on me, but it was a long, long road, with some major incidents along the way, and if I’d thought to look into such things, I might well have been better served by someone a bit less of the traditional Freudian variety, but again, I didn’t.

The fact is that on one level, I was in a lot of psychological pain and well aware of how much I needed help, and on another I continually discounted what I was experiencing as not all that serious, and not really that acute or very urgent. I didn’t see myself on a downward spiral, and I still don’t really know if I was. I may already have been moving slowly upwards, or, really, in both directions at once, sometimes feeling better—and sometimes still descending further into toxic hellspace. That’s also part of the reason why I didn’t want to identity myself as “depressed,” or “anxious” or whatever, because if I “was” depressed, then how could I also feel great sometimes? The reality is that it’s just more complicated than a single word can encompass, and that, certainly for me, a word is like a spell, and using a word like “depression” is an invocation of a place that I didn’t want to be in, or to embody.

However, there was one morning when it became very clear to me that things were really not OK for me, and that I had to work harder to change course.

Ten-thirty on a Tuesday, and I was still bleary and sour from whatever I’d had to drink with dinner the night before, in no way cured by two cups of overstrong coffee.

My work for the morning was already done. With nothing in particular to do, I was pacing the kitchen, hoping for the phone to ring. As was often the case, I might have been glad to be free of demands on my time, but I felt just the opposite. Earlier that same morning I’d been crying in the shower. I was so desperate for something to relieve my deep, deep feeling of being alone, and it felt like that was just never going to change.

There was only so much space to go back and forth in there in my flat, and I began to feel boxed in by my mounting unease. A very familiar feeling began to approach on the horizon and then to rise up within me, a feeling of dread and loss and a scattered searching for something unknown—and a question, also very familiar by then.

The question began to flash in front of me with a neon insistence.

What do I do? What do I do with the rest of the day? What do I do with the next hour? What do I do with the next five minutes?

It’s just that I don’t know what to do about feeling so alone; that feeling is so pervasive that it erases everything else and all other possibility so that I am left feeling that I literally don’t know what to do with myself in the next moment. I’ve become unmoored, first drifting, and then spinning, overcome with not knowing or not being able to see my way even into the next minute, everything obscured by sadness, aloneness, and desperation.

When I think about that now it seems clear that that was true, in that nothing of what I was doing in the habits and patterns of life was going to deliver an answer, or relief. It was a demand for something different, a demand for change—but at the time I don’t know what to do eclipsed everything else. It blotted out the sun and made my world dark.

Sensing the approach of something else, something terrible and also familiar that I’d seen in glimpses and put out of mind like a bad dream or a ghost, was pacing faster between the kitchen and living room, up and down the hall, looking for something to hold on to. By then, in that moment, all I could think of was finding an anchor, some comfort, something that would remind me that there was another hour, day, week on the other side of this desperate not knowingness, but I couldn’t see it.

I don’t know, I don’t know, I don’t know beat into me like a drum, growing louder and louder by the second. I still had almost two hours before my therapy appointment. I needed seeming to eat. Returning to the kitchen, I pulled out a loaf of bread, carved off a slice, and dropped it in the toaster, pushing the handle down until it clicked into place.

The toast gave me something to aim for, something in the future. I could just about see as far as the two minutes it would take for the toast to pop. If I could get that far, then maybe I could make it another two minutes.

A threat was dancing at the edge of my sight, and I began to recognize the shapes I’d seen hints of from time to time in recent years. Clearly malevolent, I’d always been able to push them away before, but now, with the the timer ticking away as I stood there tense and immobile, leaning against the counter for support—a maelstrom hit me, winding around me like a sheet, blinding me, and spinning me up into a white wave of confusion.

The jagged forms inside my head had leaked out into the world. My vision was taken over by a horrific rent in the barrier that normally contains the unconscious, and a spinning, spitting demon force threatened to engulf me. In this state, I saw myself from the above and to the right, looking down at my open mouth and lips as they were slashed by a cloud of whirling razor blades, leaving my face a lacerated mess of blood, flesh and broken teeth.

An cacophony of discordant bells and blaring horns surrounded me, along with a high-velocity buzz-saw whine that grew to an insane clatter. It was then that it seemed that I could feel sharp metal between my teeth, slicing into my gums—and with the blood and blades came something even worse. It was a small relief that I couldn’t smell or taste it, but I could see that it was shit. Filth smeared in with the blood, the razors cutting into me, everything mixed together in a terrifying, polluted, catastrophic mess. A foul incarnation of damage and fear and shame, and it wanted to destroy me.

It wanted to destroy me, in the sense that it was trying to tell me that I was destroying myself. The message of this waking nightmare was as clear as day—it’s was telling me that it—that is, I—could not longer live this way, that something had to change, and that wishing for someone else to change things for me would remain the fruitless, desperate hope that it had always been.

I don’t really know what to call what I experienced—a panic attack, a nervous breakdown, a psychotic break. It wasn’t so much a literal hallucination as a outburst of psychic energy that forced its way upwards from my unconscious so strongly that it took over my senses for a short while. It doesn’t really matter what to call it. It was frightening—and I knew that it was a manifestation of something deeper. I couldn’t fully digest it at the time, but it was clear that it was a message, not an unhinging into further damage.

Gripping the edge of the sink, my heart pounding, I gasped for air, filling my lungs as I started to become aware of my surroundings again. Sweat dripped from my arm- and elbow-pits. My ribs and chest felt as if they were splayed wide open, letting the cold, foggy air coming in from the deck blow right through me.

I turn to look at the cheap plastic toaster full of glowing electric fire, my gaze following the black wire to where it’s plugged in between jars of coffee, beans, and spices. Pots hang on the wall behind the small gas stove, a relic from another era pushed in between cheap IKEA cabinetry and wide-planked softwood floors. On one wall hangs the painting I bought in Paris a few years prior. The other three walls remain white and empty.

The smell of hot bread arrived just before the toast popped up, just two minutes after I’d pushed it in.

I was still unsteady and weak as my arms moved shakily to paint the toast with almond butter. I knew it would feel good to eat. The clamor in my head was subsiding, my senses returning to normal.

* * *

Five minutes later, sitting at the kitchen table eating my toast, it occured to me that I really did need more help. Nobody else could change things for me, but I needed more of my people to know what was going on for me. I needed to let it out, so that it wasn’t just inside me. I needed to begin to spell it out.

My old friend Anni had just moved back to San Francisco after several years in art school out on the east coast. We ran with the same crowd in our teens, never really close, and then run into each other online as soon as she was in town again.

I opened my computer and pulled up her profile on Nerve, which was a very mid-aughts combination of sex-positive online dating and R- to X-rated writing that made a lot of people curious, but never really took off in a big way.

My heart rate had slowed from the whirlwind attack, and now it was increasing again at the prospect of sexual connection.

I typed words into the little box on the screen:

I just kicked my ex-fiancé out of my apartment, so I thought I’d see what turns up on Nerve. Busted! Nice to see you here.

Anni must have been staring at her own screen on the other end, because her reply came back almost instantaneously.

You fucker. I love you.

Feeling a wash of relief, I hurried to write back.

Wanna get drunk and screw? You could help me exorcize hellbitch juju.

More glowing words appeared in front of me.

I’ll come over later. We can break things. Seriously, what’s your address?

* * *

I don’t know what we broke that night when she came over, and I didn’t tell her or anyone else what happened to me that morning for many years, but I did let her in on how lonely and lost I was feeling. She showed me that I could tell someone that, and that they would hear me. Anni was in her own fragile place at the time, and still, she looked after me. She called me, she checked in on me, she invited me in. We helped each other, I think.

Anni showed me that someone was watching, and she was the first woman in my life who became not just a lover and a friend, but a sister.

That vision never returned, and although it’s message wasn’t entirely clear at the time, I could see it for what it was—a cry for help, and a stern warning.

Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, the book-length memoir about a man learning to listen to himself, and the price I paid until I learned how to do that, serialized right here on Substack with a new chapter published every week.

You can find everything from the memoir that I’ve published so far right here.

DECIDE NOTHING is a reader-supported publication. To receive new posts and support my work, please consider becoming a free or paid subscriber.

Further reading

Here’s the table on contents for the memoir. You might also enjoy some of my other work, such as

or any of the other essays that you can find here

What does this bring up for you?

1. Have you ever experienced a panic attack, a nervous breakdown, a psychotic break, a waking nightmare, or anything like what I describe in this chapter?

2. What has been your own experience with “anxiety” and “depression,” and coming to terms with those terms?

3. Have you ever gotten a warning from your own unconscious that was too strong to ignore?

4. Has a friend shown up for you somehow in a new way?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

Jenna had her issues, but I can’t lay much blame with her. I cooked us up quite a mess, and although it took less than a year to unwind, start to finish, I was thrashed. I knew that I’d made a serious, damaging mistake—a whole series of them, really, and I was deeply ashamed about all of that, as well as hugely depleted from having put so much energy into the relationship. Attempting to commit to and ’work on’ something that was really better seen as a work of a fiction was tragically heartbreaking—and ludicrous—and also infinitely more taxing than whatever work might have been required in a relationship built on some actual foundation in the present.

No wonder I was wrecked. I’d been hammering myself into an impossible shape, and the only possible result was frustration, heartache, confusion, anger, resentment, and breakage.

It’s sure as shit that I was well and truly broken up about having to admit that the engagement was a total sham, but things weren’t all bad on my end. Not at all. There was some good that came out of the debris.

For one, as anxious as I’d been to leave the City before going to grad school, and as committed as I still was to leaving San Francisco as frequently as possible, it had become clear to me that I did actually want to spend more time at home, and to get to know people there better. It wasn’t lost on me that my burgeoning business was all about creating community for other people, and that at the same time I wasn’t really part of that community, and with all of my constant coming and going in my twenties, I often felt like a stranger in my native city. I was someone with lots of acquaintances but few close friends, and with a tenuous, conflicted connection to a place that I loved deeply, and was constantly trying to escape. When I left for Wisconsin I had no particular plans to return, and I wasn’t aware of having chosen to bail because I missed being in California, but the feeling of home is deadly attractive.

Even if I’d ended up there unconsciously, at least I was at home, and once I was back in San Francisco, I forgot my life in Madison as quickly as I’d left. I’m still reluctant to use the word “roots,” but I did resolve to focus at least some of my energy on where I was from. For the first time in my life, I knew I needed more stability. Traveling was already a skill that I’d accumulated in depth, but I saw that the greater challenge was to stay, and what I needed to do, even if I didn’t see it as permanent.

The place that I was now living in by myself was in Potrero Hill—considered by many the most ”San Francisco” of all its quarters, a hard-working village-within-the-city of class-A Victorians on solid bedrock, close enough but not crowded up against the shoreline of the Bay, and home to sailing captains, stevedores, railmen, brewers and butchers, Potrero was set well apart from and not at all like the dressier Telegraph, Russian and Nob hills north of Market Street.

The Hill never really developed much of its own downtown aside from two blocks of 18^th Street, with a couple of restaurants, Farley’s famous coffee shop, and one bar—Blooms, a standard neighborhood dive until you find your way past the pool table to the one lone booth in back with a window that gives onto a million-dollar view of the entire southern city. The wide streets, most named for states, make for an unhurried pace as well as beautiful light, and homes on the hill are often sheltered from the famous San Francisco fog by Twin Peaks, lying to the west. Potrero Hill feels unfussy, timeworn, and egalitarian, and yet far more spacious and urbane than the tight blocks of Bernal Heights, the next hilltop ‘hood to the south.

By the time Jenna and I split, I’d also sold the house in front of the bus stop that nearly drove me over the edge, but that was only a few blocks away in the Inner Mission, and I could walk down to my old neighborhood by using the pedestrian bridge which crossed Highway 101 near 18^th street. Although I’d never been there when I lived just around the corner, once I was on my own again I rediscovered a huge indoor climbing gym called Mission Cliffs, and began to go here often for exercise and some minimum of social interaction.

Especially in the grey, wet, lonely winter that followed the end of our ill-fated engagement, the vibrant, colorful scene at the climbing gym was a welcome relief, and although I was beleaguered and depressed, hungover and overweight, I loved the feeling of climbing again, and I appreciated that I could show up solo and the front desk staff would make a friendly PA to hook me up with a belay partner. While the fantasy of course was that this might deliver up a lithe female wall-rat in tight shorts, with her phone number at the ready, the reality was that women could undoubtedly sense the angst and desperation radiating from where I stood in the waiting area without even looking in that direction. I never did meet any women there, and in fact I only really met one person that I ever stayed in touch with, but he ended up becoming a very close friend.

Nearly ten years older than me, Peter was handsome and self-assured, and offered a reasonable, welcoming, un-macho presence. He didn’t quite have the stature or the booming voice to be senatorial, but he did have an impressive educational pedigree, along with intelligence, vulnerable honesty, and a remarkable Yankee lineage that connected him directly to the founding fathers. Like me, he was depressively organized, prone to misunderstandings with women, and also liked his wine, although he lacked my compulsive and unhealthy attachment to over-drinking.

He was also the first therapist or psychologist I’d ever met on a social basis, and I was both very much in need of his counsel, and also just dead curious about what it was like to be someone who did that work. I was fascinated, really, to the point of being enamoured with his professional self, and what’s more, we got along as climbing partners.

This new friend and I began to meet once or twice a week for lengthy climbing sessions, often followed by dinner at one of the latest crop of new-school Cal-Ital restaurants that had popped up in the Mission in recent years. Peter was the first full-grown man that I’d made friends with as an adult outside the context of my business life, and also not entirely based around consuming alcohol, and the fact that this guy liked me enough to keep showing for gym and dinner dates did a lot to bolster my self-worth. The climbing was good for me too, and especially since I was the bolder and more agile of the two of us, my ego got a stroke along with the workout. I admit to having sometimes complained that his company was a bit of a downer, but that’s also part of why we got along, and what we had in common. It was also Peter that finally helped me to find a real therapist, one that I ended up seeing for the following several years and, in the process, finally cracked something of my shell.

Along with Peter, I began to form some other real friendships in those years as well. Although I very thankfully failed to commit well enough to lock myself into marriage, part of the actual commitment that I did make following the disaster with Jenna was not only to stick around in San Francisco and stay in the same house without moving for a while, but also to deepen my relationships with some of my old friends.

In particular, I began to ring up my old buddy John, a guy I’d first met in my first year at Lowell High. I was a underaged freshman of just thirteen, and even though he was a senior, somehow we hit it off well enough that he became my entrée into the entire San Francisco house party scene that became, for better and for worse, the main social world of my teens. We’d been friends for ages, but also never really had much of a conversation. I knew he was capable, and that I’d just never bothered to go there.

John had a certain way of holding his body, perhaps informed by his family’s history as circus performers but that reminds me more of classical sculpture, his torso turned slightly, chest open, and arms lifted in a Greek orator’s pose, his long hair draped over his thick shoulders and down his back. He’d graduated with a major in archaeology and spend serious time on digs in Israel and on native American sites here in California, but then dropped his graduate work in favor of becoming a DJ in the nineties house music scene in London. Already shrinking in height and growing more round in his late thirties, John had become a Michelin-class home chef, brewer and winemaker, crushing grapes gleaned from name-brand Sonoma vineyards in a spare bathtub on the back porch. I once smuggled him a dozen or so oranges from a trip to southern Spain, and he repaid me a month later with a jar of handmade marmalade, and we continue to share a love of inventive cooking, bacchanalian dinner parties, and elaborate dinners.

There was a Thanksgiving in there that we co-hosted that he and I embarked upon not so much for the guests as for the pleasure of working together in my little kitchen for hours and hours, opening and drinking bottle after bottle of wine while challenging ourselves to come up with yet another dish that we could somehow compose and manage to cook off, all on my 24” vintage Wedgewood. Pushed along by adrenaline and plenty of fine juice from the Sicily and the Loire, we managed to stuff the turkey in the tiny oven, perfectly roast it, and lay everything out on the table for our dozen-or-so guests—and then, with our work complete, collapse—the both of us, right there at the table, faces in our plates. Our guests enjoyed the holiday, I was carried off to bed by yet another dear friend and lover, and the night was not forgotten.

These old and new friends, John and Peter, were two of the first men that I felt really had some idea of who I was and what I was struggling with. I’m sure that in part because I finally felt free enough to be open enough so that they could see more of me, but it’s also because they’re both caring, insightful and generous people. I was grateful then, and even moreso now, for their friendship, attention and companionship in those years. Both played a key role in reopening the possibility for me of close relationships with other men, something that would become more and more important to me in later years. Both were and are brothers that I had little of growing up—benevolent and if not quite affectionate, at least steady in their presence in my life.

Being significantly older than I, Peter also felt like an uncle and even something of a father, which in turn helped me to begin to gradually reopen a connection with my own father.

In addition to finally beginning to have some real friends, the little niche that I’d carved out with my conferences over the course of the first half of the 2000’s was slowly turning into a real business. It was still tiny by most standards, but I was able to pay myself a salary in the low six figures and began to hire my first employees as we produced a half-dozen or so events each year, not just in the U.S. but in Europe as well. By 2008 we were pulling in over a million a year in revenue—an undeniable milestone that also signified something with some staying power.

I loved a lot of things about it—working for myself, being able to make decisions on my own, creating a great experience for other people, and flying off to the various locations that I chose for the conferences on a regular basis—and at the same time, I was very conflicted about it, because I couldn’t escape the fact that the conference was all about… of all things, advertising. Even so, it netted out as hugely positive, with the benefit along the way that by this point I had no trouble paying my bills, and plenty of spending money.

Despite my lack of social success at Mission Cliffs, it also wasn’t all that long at all before I began to meet other women—and not entirely online for a change. I met someone at a backyard BBQ who was impressed enough with the salad that I brought to give me her number, and another at Burning Man who fulfilled my teenage fantasy of being lucky enough to be chosen, if only for a short while, by the prettiest girl in high school—and then blew right past even that great wonder by offering to cut my hair, topless, on my back deck. That right there is a subtle and delicious sensual pleasure that I will never forget.

My ruinous run-in with attempting something even seemingly serious gave me the latitude to stay strictly in the realm of the casual for a while, and I had a string of delightful girlfriends who, as they passed from acquaintances to lovers to friends, would return to my place on the Hill there for parties again and again, filling the room to overflowing with their sweet female presence and showering me with their beauty, love and charm.

The climbing gym was good for me, but I longed to feel more adventurous, to move more outside. I had the outdoors in my blood from an early age, and Peter tried to get me into other sports that he enjoyed—cycling, and whitewater kayaking, but neither really grabbed me. I’d been a sailor and a skateboarder all my life, then hurt myself windsurfing and had to hang that up, but the climbing and bike riding had made me a bit stronger, and so when I finally caught a glimpse of some kitesurfers making turns on the swells outside the Golden Gate one late summer day in 2007, I felt able and inspired enough to give it a shot.

All of the sailing I’d done, along with a lot of snowboarding and even a little surfing made the idea of holding a sail—or a kite—while standing on a board make sense to my body straight away. I took some lessons from a mellow young guy whose friends at the beach called him (of course) “Hollywood,” and by the early summer of the following year, I was able to go out at Crissy Field, the double-diamond expert local spot right on the northern city-front, with a direct line upwind to my beloved Golden Gate.

Despite its slightly silly-sounding name and the reputation that it unfortunately acquired for becoming popular with the burgeoning class of so-called tech bros, kitesurfing felt very real, very elemental, and very much a version of sailing to me, and San Francisco is city made for sailing. Since I worked for myself, I was able to head across town to Crissy whenever the wind was up and the sun was out, and my frequent attendance at this new aquatic church was a major healing force.

Until then, I hadn’t ever developed a ongoing practice of outdoor exercise that was anything more than sporadic, but after I started kiting I was out there almost every day. I formed a deep relationship with the sport in way that had never happened for me in the past, and part of that was with the people. As I became a regular at the beach, I gained a whole new circle of friends that I knew and respected based solely on our mutual love of the sport. Many of us didn’t know what each other did for a living, or even each others’ last names for many years, as focused as we were on hauling ass across the fifty-two degree water of the Pacific as it mashed up between the headlands, pulled along by wind howling in through the Gate from the west.

That environment, the exposure, and the elements reawakened, enlivened, and strengthened my constitution. I felt stronger, capable, and free in a way that I hadn’t in a long, long time, if ever, and the feeling of being able to roam the bay under my own power gave me a feeling of physical confidence and creative power that carried over into many other aspects of my life.

I often still felt desperate, and therapy often felt like a torturous standoff, doctor and patient both silently waiting for who would break first. Of course it had to be me, and over time, I did, layer by layer. I was still drinking too much and too often, and as my business grew I was traveling again more and more—and I certainly wasn’t moving towards any sort of steady relationship, but still, something of a center was beginning to form.

Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, the book-length memoir about a man learning to listen to himself, and the price I paid until I learned how to do that, serialized right here on Substack with a new chapter published every week.

You can find everything from the memoir that I’ve published so far right here.

DECIDE NOTHING is a reader-supported publication. To receive new posts and support my work, please consider becoming a free or paid subscriber.

Further reading

Here’s the table on contents for the memoir. You might also enjoy some of my other work, such as

or any of the other essays that you can find here

What does this bring up for you?

1. Have you ever made a major life error—and how did you recover from it? What did you learn?

2. How have physicality, fitness, and sports played a role in your life, and in your psychological and emotional well-being?

3. If you are a man, when did you start to form deeper friendships with other men?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

Three-quarters of my way through the masters program in Urban Planning at UW Madison, I had the chance for a quick trip back to San Francisco. Along with my coursework, I had an R.A. job on campus sixteen hours a week and the beginnings of a conference business up and running, but when a quick consulting gig popped up, I was happy to jump on a plane for a free trip back home, not to mention the extra cash.

Knowing that I’d be in town for a few days, I did what I’d often do in those days and dropped a note to someone that I felt would be open to getting together. Jenna was a woman that I’d dated for a while in my twenties after meeting in the sweaty downstairs disco basement of a joint called Nickies on lower Haight.

Along with that Swedish chick that I pulled from Vesuvio, Jenna was one of the few women that I’d ever met in a bar. I was always pretty useless at meeting people that way, but there were a few, and in this case I’m proud to say that I remember her saying that it was my dancing that prompted her to give me her number that first night.

I flew out on a Thursday and we met for dinner on Friday. I hadn’t seen her in some areas and when she showed up, I was floored again by this striking, strong woman—still something of Marlene Dietrich meets Bettie Page, now grown into herself, with lithe, athletic sheen to her skin.

When we’d split before it was copacetic, and at this point we both had a few years of real adult life under our belts. I think we were both impressed with each other. She’d been doing triathlons and had what sounded like something of a career going, and my story sounded pretty good too, between grad school and the business I’d started. I didn’t get home until after midnight, and I was feverish with excitement.

The very next day, I found myself walking around Hayes Valley with my buddy Rich on one of those warm, bright days of late spring that always reminds me how much of a maritime city San Francisco really is. The sun was out, and I was enjoying the fresh sea air rolling down the hill from Alamo Square as I cruised happily down the sunny side of street, on my way to one of my favorite little shops where I’d become acquainted with the owner.

Scanning down the block, my eyes connected with a familiar set of curves. Long, wavy chestnut hair, jeans tucked into motorcycle boots, a saucy set of lips set below eyes just a little bit too close together. I’d just seen her the night before, and it took me less than a second to see that is was Jenna again.

Her eyes crossed my path as I watched her swinging down the block, and a wide smile broke across her face like a wave.

We’d left dinner the night before without any plans to be in touch, but as a visitor to San Francisco for a change, my heart swelled at a familiar face on the street, and it sure seemed like something sweetly meant to be when we bumped into each other like that.

* * *

Back in Madison, I was a year and a half in, and the only part of the question of what I might do once I was finished there that had become clear was that I wasn’t at all cut out for a job as a city planner. I’d figured that planning might be a way to put my interest in urban geography to work in a practical way, but after sitting in on just one of those interminable public planning review meetings, I’d had enough.

Bureaucracy sure ain’t my thing. I’d been looking at my other options, and at the same time, the series of conferences that I’d started in ’99 had begun to spin off a little income without even too much work on my part. In the meantime, my life on the ground there was A-player grad student by day, and dirty as dirt got by night.

Although I’d gone out to Madison in partnership with yet another girlfriend, we split not long after we landed there. Reverting from vanilla boyfriend to sex-focused boozehound, I set up my usual shop on the usual sites, and before too long I managed to meet the one female person in town with similarly straightforward obsessions.

Lola was just like me—an over-sexed, dedicated drinker with a day job that kept the lights on, but who lived mostly at the keyboard, and more at night than out in the daytime world. She was a bit of a writer, and had a Tumblr site where she posted anonymous accounts of her exploits in the sexual underworld. I was actually doing a little bit of the same—blogging, it was called in those days—and we connected immediately over our love of peanut butter Captain Crunch, Maker’s Mark, kinky sex, and our mutual willingness to put some of our experiences out into the ether.

I’d escaped the street noise and domestic chaos of where I’d been living in San Francisco, and Lola and I got a nice little thing going, which really did help, but I hadn’t escaped the growing unease and disarray of my mental and emotional state. By this point, I was aware that I felt some sort of “depressed,” that is, certainly down more than up, and now with Lola as a steady drinking and sex partner, I was always sleep-deprived and hung over, which just made things worse, week after week.

After a night with her I’d roll out of bed with just enough time to french-press a large cup of over-strong coffee, my head not so much splitting as melting in sickly, slow green fire, push myself into the shower, and then, rejuvenated enough to greet the day, jump on my Vespa to ride across town to campus. I already stood out enough as one of the few people in the program over thirty, and I’m sure my outfit of cut-off, rough Ben Davis work pants, bleary, bloodshot eyes and a whiff of sex and hard alcohol from the night before only reinforced the impression that I was perhaps better left alone.

I sort of had it going in all directions all at once. Work and grad school were going pretty well, I was teaching sailing at the club on the lake, I had a steady girlfriend and I was even going to yoga some afternoons—and, I was drinking and up late every night either with Lola or online, and seeing a campus shrink, none of which was enough to compensate for the hole in my heart that kept getting larger.

To top it all off, just before going to San Francisco I’d been up to northern Wisconsin for an idyllic weekend with my grad-school friend Jamie and her two young kids. Jamie was like a sister from the start, and it was always platonic between us—and we were close from the start, and still are. One day she and I took her son and daughter—both still small enough for me to pick both of them up together, one in each arm—on the ferry to the Apostle Islands, a tiny, verdant archipelago extending out into Lake Superior. It must have been a weekday. On the way back, we found ourselves as the only passengers on the old square ferry as it cruised slowly back towards the town of Bayfield in the brilliant late-spring sunshine. I led the kids up the steep stairs to the open door of the pilothouse, where the captain beckoned us inside. Minutes later, first the five-year old girl and then the three-year old boy took their turn at the helm of the hundred-ton ferry boat as both of us adults encouraged them to look back at the wake to see how they were actually steering the thing back and forth. It was just a moment, but that was a powerful glimpse into of what being a husband and father might be like, and a very dramatic contrast to the manic, unsettled pace of my daily life.

* * *

All of that’s to say that running into Jenna that Saturday back in San Francisco felt incredibly serendipitous. I was hungry for an out—and to prove that I could join the ranks of men who’d found a good woman willing to be their wife. Even though I was more and more comfortable in the sexual underworld, at the same time I wanted to know, and to show that I was not a bad man but a good man—and as far as I knew, to do that, I had to “commit,” which seemed to be shorthand for signing up to do what you really didn’t seem to want to do, but sort of knew that you “had” to do. I was also desperate for connection, for stability, for normalcy, for being part of something, for family, even.

That was beneath the surface though. What I felt in the moment was excitement, gratitude—and not a little bit of magic—and I have to say, she seemed pretty happy to see me too. We only had a few minutes together there on the sidewalk, but I was used to making things happen, and so before she slipped away, I suggested we that have dinner again while I was still around—and why not that very night?

She said yes, and I was walking on air as Rich and I continued our tour of the City. Passing Tiffany’s downtown on Grant Street an hour or so later, I was hit with a crazy idea—and by the time that we met for dinner, I knew what I was going to do.

Jenna and I met for dinner in a place that I chose because it was in a part of town where I’d always wanted to live. Potrero Hill was certainly not the fanciest but one of the oldest and most characteristic neighborhoods of the City, with views of the skyscrapers in the financial district, out to the cargo anchorage south of the Bay Bridge, and across to port of Oakland. We sat together as old friends, feeling the warmth of connection rekindled as I worked up my nerve.

I was determined, and I knew from not only my working life but also from my many interactions with women that there was a certain sorcery in that conviction. After paying the tab, we walked up the hill to take in the view, and I knew that while what I had in mind would be surprising, she wouldn’t reject me. As we stood on the quiet corner of Carolina and Southern Heights, taking in the view and reminiscing about our love of San Francisco, I came out with what had come to mind earlier that afternoon.

“Here’s what I’m thinking, Jenna.” I took a breath, not in hesitation, but because I could feel the weight of the incantation that I was about to speak.

“You and I should get married.”

“What? Wait. Are you serious?”

She was shocked—and delighted. She laughed gently, already digesting the possibility.

“What about your masters?”

“I’m not gonna be a planner. My business is doing well enough that I can come back here, we can get a place right on the Hill, and I’ll be happy, together, with you.”

She was thinking, but I could tell the spell was working.

“You really think we should?”

I already had my stake in the ground. “Yes, I do. That’s what I want to do. That’s what we should do.”

She called me the next morning and I went by her place on my way to the airport. She accepted my proposal, and better than ever at doing, and still completely cut off from feeling, I went back to Madison, packed up my apartment, flew off to Europe for one of my conferences and then back to San Francisco, found an apartment for the two of us, and within a matter of less than six weeks we were shacked up together three blocks from where we’d had dinner, as if that had been the plan all along.

The truth of it? I’d say that I have no idea, but that isn’t true either. The truth was that, just like my parents had when I was a kid, we both avoided the truth even when it was staring us in the face. After all, Jenna and I had been together for at least a year in our mid-twenties and ended it cleanly because it was obvious that we didn’t have enough gas back then—so why would we now?

The truth of it was right there for us to see from the start, but we insisted on ignoring it. The truth of it was also right in front of me during a short encounter that occurred on my trip to in Europe before returning to join her in San Francisco.

I flew to Tallinn, a stunningly preserved medieval merchant city guarding the eastern reaches of the Baltic Sea as it stretches eastwards towards the Russian city of St Petersburg. It was the summer of 2004, and I’d chosen the location because Estonia had just joined the still-nascent European Union and I wanted to see the place before it was swamped with British weekend stag-and-hen partiers, and to bring our business there as a sort of congratulations to the Estonian people.

The conference went off well, even through this was only the second or third one that I’d organized overseas. On the final night, I went out to celebrate with a few of the participants, themselves all young Londoners who were already savvy to the party potential of this attractive place that was just an hour’s flight from the UK. Along with being inexpensive, like many Eastern-European countries Estonia was also known for attractive women, and the subject was on my mind as we finished dinner and stumbled out into the streets, lit by the glow of the late night mid-summer sun hanging just barely below the horizon. Not wanting to be observed in my pursuit of flesh, I made a point of losing my companions and before long found my way into the vast cave of a strip club.

I was half drunk, and my usual backstop of a tab of Tramadol blurred my perception in a way that I enjoyed at the time. I wandered through a dark maze packed with bodies, a small theater, a balcony, many doorways, lights and shadows. Growing weary, I ended up by myself in a dark downstairs booth, drawing the curtain closed behind me.

Despite my fervent interest in sex of all sorts, I hadn’t been someone who pursued dancers, strippers or prostitutes, and along with my state of inebriation—and very much aware that I’d just announced to everyone back home that I was going to be moving back to San Francisco and getting married—and that the woman who was effectively my fiancé was waiting for me there while I jetted off to Europe, and already having sensed the unreality of what I was getting myself into at home, I was in a wretched state of denial, and already beginning to despair at my dilemma. I didn’t know what I wanted. I thought I wanted to get married—and I also wanted to at least see what had been advertised on the posters outside the club.

A hand appeared and pulled back the curtain, revealing an arm, shoulder, breasts, and then the body of a young woman, who smiled and slipped into the booth with me. She couldn’t have been more than nineteen, and there couldn’t have been more contrast between us as we arranged our limbs in the tiny stall, pretending it was all natural enough that she was sober, slim, and entirely naked, and I was bleary, bloated, and spilling out of the suit that I’d bought just a few days before on the same block in San Francisco where I’d run into Jenna.

I just sat there goggle-eyed and immobile.

I’m sure it wasn’t the first time the person tangled around me had gathered that a client of hers felt conflicted. Finally, she broke the awkward silence and asked, “what do you want to do?”

I didn’t even know what might have been allowed, and I was too drunk for sex anyhow, but my situation back at home was so much on my mind that I thought she was somehow referring to that.

“I’m getting married,” I said, “I just want to look.”

She recoiled to create space between our bodies and turned her eyes back at me. They flashed unearthly neon blue, her skin glowing radioactive in the UV light—and then she shook her head, palmed the cash the I offered, and slipped out through the curtain, leaving me there in the dark.

* * *

Jenna and I were both very clearly hoping for a Hail Mary into family life. We knew it wasn’t meant to be—we just couldn’t bear to admit it. The week after my trip to Europe, I was back with her in San Francisco in her little Presidio apartment, and to her great credit she did come out and ask, “Do you really think we should do this? We don’t have to go through with it, if you have any doubts.”

I did very much have doubts, and I knew what she meant was really something more like ‘I wish I had the courage to tell you that I have some very serious doubts here. In fact, all I really know is ‘no,’ but I’m afraid to say that, and so I want you to say it,’ but I didn’t have the balls to do anything but insist that we carry on, just as I had when I first proposed.

She also told me that she was taking antidepressants, and asked how I felt about that. What could I possibly say, other than “no problem, of course?” I’d considered doing the same myself that same year, and I was still unclear enough on my own depression and how I felt about pharmaceutical intervention that I swept right by the whole subject, even though it should have been a major red flag.

I should have turned around, closed the door and split back to Wisconsin to finish my bid at grad school. Instead, I said, “Don’t worry, it’s gonna be great,” even though I knew even then, without a shadow of a doubt, that it was going to be about as great as when someone says “This won’t hurt a bit,” right before they land a right hook to your jaw—and that when someone says “don’t worry,” that’s often reason enough to do just that.

The feeling of home is deadly attractive. I doubled down, dropped out, and ran for what seemed like home—and less than a year later it was over, she was gone, and I was alone again.

It wasn’t losing her that hurt so much. We never really had all that much of a good time together unless we were drinking anyhow, and even then, lemme just say, I’m sure it had a lot to do with me as well, but this girl, she seemed cold, sharp, and hard. She had her reasons, but that didn’t help. We were both depressed, and I can only conclude that she must have been feeling as hopeless as I did, because why else would she have agreed to such a dumb-ass moonshot?

What fucked me up about Jenna was losing the story—or how the story changed from a happy, romantic accident that included the ridiculous fantasy of getting married and having a happy little family together to the reality of the fact that I’d been desperate enough to betray myself again, dropped everything for an illusion and a lie, really, and chucked it in together all the while knowing better—and then suffered through a full year of very painful dissonance, including the pathetic joke of several couples therapy sessions which only served to emphasize how deeply committed we were to deceiving ourselves.

I remain convinced that the only way to make a real mistake in life is to knowingly contradict your intuition, and that’s exactly what I did, yet again.

Even though we were both complicit, I felt at fault since the whole damn thing had been my idea in the first place. I ended up minus not just a diamond and a check to help her get back on her feet, but also with a big stain on my mostly-imaginary vision of myself as a husband with a wife and family. I was a fool, the proposal was an error, and the engagement was a wreck.

That story, the real story, hurt bad and it hurt for a long time. Somehow I’d managed to fail to commit on both ends, having quit my masters program and then also this dead-end engagement—and even just the fact that I’d have to admit to having been engaged and not married for the rest of my life seemed like a pretty shitty card to have dealt myself. Once again I’d gone purposefully into the zone of confusion, and once again I’d given up my own path for someone else’s, and my reality for some invention I cooked up somewhere else, with someone that I already knew that I didn’t love enough.

I couldn’t believe that I’d been down so much of the same road before, with Julie in Ann Arbor and Seattle—and at the same time I knew exactly how it had happened. I’d lied to myself and everyone around me, and again I’d persisted in trying to force things into a configuration that I could see very clearly it was not going to take the shape of.

We both felt like shit, and I was wracked with remorse and shame.

Other than empty congratulations, nobody said a word to me when I announced that I was going to drop out and move back to San Francisco to get engaged to an ex. Nobody asked me anything, or questioned me, or suggested that I think about it, or wait, or reconsider. Nobody said a word.

So much for grad school.

Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, the book-length memoir about a man learning to listen to himself, and the price I paid until I learned how to do that, serialized right here on Substack with a new chapter published every week.

You can find everything from the memoir that I’ve published so far right here.

DECIDE NOTHING is a reader-supported publication. To receive new posts and support my work, please consider becoming a free or paid subscriber.

Further reading

Here’s the table on contents for the memoir. You might also enjoy some of my other work, such as

or any of the other essays that you can find here

What does this bring up for you?

1. Have you ever made an actual life error? I’d love to hear your story! And, how did you recover from it? What did you learn?

2. What is your own relationship with your intuition?

3. What’s your own experience with marriage, and the pursuit of normal?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

A ceaseless hum of outdoor noise filters in through the old plaster walls as I sit at my desk—the same graffitied tilt-top from my high school room on Church Street. Nominally, I’m working from home while I recover from back surgery for a blown disc that I suffered six weeks prior over the Y2K New Year, just before my thirtieth birthday. In reality, I’m marking time with no specific end in sight, trolling the web and feeling a nice buzz from the Tramadol that I take for the pain the surgery was supposed to alleviate.

My laptop is open and I’ve been sitting there for a couple of hours already, flipping back and forth every few seconds between bank statements and my email, hoping for a message from someone else out in the ether who happens to be searching for a particular kind of sex on a weekday morning, when the bus comes by downstairs. The monster machine grinds to a stop at the corner right outside with a squealing complaint from the brakes and a gargantuan, exhausted fart as it squats to swallow a load of passengers, all the while emitting an interminable series of high pitched safety beeps. Finally the doors judder open and there’s silence for a few seconds before the bus roars to life again and lumbers away, funneling diesel exhaust from the angled stainless steel stack directly upwards towards my home office window.

Just as the sound of the bus is finally receding, I watch wide-eyed as a wheezing, humpbacked Sunset Scavenger garbage truck bangs up in front of the apartments across the street, trailing a stream of dribbling waste from its rear jaws. Leaving the rig running, the driver jumps out and skips up the steps into the building, the rain cap on the exhaust stack clattering along over the idling diesel like the muppet drummer Animal bashing on his kit.

I hit command-R a few times in quick succession, as if that might conjure something to appear in my inbox, but it remains empty as the trash truck sits there clattering. I picture the driver inside having lunch with his wife, maybe some leftover enchiladas and a Coke—but I’m all by myself, and I’m gripping the sides of the desk like a life preserver, wishing for some quiet.

How could I have been so naïve as to not have noticed the city bus stop literally right outside the front door before buying my first home? You’d think I would have seen the signs—or the riders who I often find patiently waiting on what is now my very own front stoop. The fact is, I’d made a mental note some years prior to never again make the mistake of living on a busy street and yet in my haste to take advantage of what seemed a timely opportunity, I’d forgotten my own advice to myself and ended up precisely where I didn’t want to be.

My buddy Ted and bought the building together the year before, just before I went in for surgery. A gifted songwriter and natural front-man, I loved the way he seemed able to be himself without thinking about it, but Ted was also prone to mania and anger—and this handsome, charismatic, rock-star of a guy was a super-magnet for bad luck. At this point he was raising an infant daughter in the downstairs flat, picking up bit parts when he could, and driving a cab for cash. Neither of us were made guys by any means, but this was before even the first tech boom, and a two-up B-class post-earthquake Edwardian in the lower Mission didn’t cost anywhere near a million yet—in fact, I think we bought it for about $550,000—not bad for two full flats with a good coffee shop around the corner.

Ted wasn’t exactly my ideal partner, but he was an old friend and when he came to me with what appeared to be a deal, I felt like it was finally time to buy into a piece of my home town. We didn’t have idea know how naive we were though, and we were being led by the nose by an unscrupulous realtor ‘friend’ of his who didn’t say jack about how we might deal with the half-dozen existing tenants.

When it came time for us to move in, they were all cool except for one random dude who decided to make it his mission to try to extract that maximum from his fortunate circumstance. We were in the right—and we weren’t aiming to “evict” anyone, but we did want to live in the house we’d just bought—but our attorney fucked up the paperwork and we ended up getting sued, and lost. This guy was squatting in what was to be my flat, so I had to wait for this all to be resolved before I could even move in.

The trashman’s probably having his siesta. I’m sitting there, heavy breathing and staring at a jumble of figures on my screen when it dawns on me that Ted has already missed a couple of his half of the mortgage payments. Six months into our deal, and our joint account is headed towards the red zone—and just then, a Harley with open pipes slow-rolls through the four-way and then blasts down the block in second, setting off an overlapping cacophony of novelty car alarms with the synthesized siren sounds of a hundred cheap plastic toy space pistols.

My mouth hangs open in frozen disbelief as yet another wave of sonic chaos crashes over me. I’ve got a place of my own for real, but at the moment it feels like it might have been a mistake. I try to shake it off, but I’m short of breath, and my heart is beating triple-time. I’m starting to feel a familiar, desperate feeling—the feeling that I don’t know what I’m going to do, or how I can do anything, really, when something else happens—something outside of my normal experience, something ill and seemingly ill-willed.

I feel my skin go cold as this loathsome and terrible something tries to force itself into my perception. It doesn’t make any sense, but yet I can’t avoid a glimpse of a fearful sharp-edged whirring. I blink my eyes and see like bright flashes within a filthy cloud that swells with threat. It’s coming from inside me, and it’s also clear that it’s trying to get out into the air of the room around me as I sit there at my desk.

Whatever’s rising from the unhappy depths, I’m damn sure I don’t want to see any more of what it is, and I gather my will to shove it back down into my unconscious.

As soon as it subsides, the brief buzz of the unhinged is replaced by the glowing coal of the inflamed nerve in my back pressing against my chair. Scanning the room for relief, my eyes land for a moment on my favorite pin-up calendar. One girl for each month, their signatures scrawled in Sharpie over images of them making sexy eyes in dirty welding gear under the sign for a local metal shop: Complete Fabrications.

None of those girls are calling me. I’ve seen a therapist a couple of times, but I have no idea how it’s supposed to work, or how or when it might help. Nobody explains anything.

I take a couple of deep breaths, doing my best to ignore the cluster of filthy house-pigeons that gabble on the windowsill, which is covered in bird shit and a pall of black particulate dust. The noise leaking in from the street seems to back off for a moment, and something bubbles to the surface of the sea of static in my head. Holding back tears and willing my heartbeat back towards normal, I turn back to my computer and pull up my bookmark for the grad school at UW Madison—the leafy, sedate, lakeside state capital of Wisconsin, and begin to fill in the application.

Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, the book-length memoir about a man learning to listen to himself, and the price I paid until I learned how to do that, serialized right here on Substack with a new chapter published every week.

You can find everything from the memoir that I’ve published so far right here.

DECIDE NOTHING is a reader-supported publication. To receive new posts and support my work, please consider becoming a free or paid subscriber.

Further reading

Here’s the table on contents for the memoir. You might also enjoy some of my other work, such as

or any of the other essays that you can find here

What does this bring up for you?

1. Have you ever had to make a desperate exit? I’d love to hear your story!

2. What’s your own experience with mental health, anxiety, and instability?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!

When I look back at those last years of the nineties, it feels like a blur, and a binge. I was working the back half of what had unexpectedly become a first career in what had already started to be called “tech,” and it was starting to be clear to me that I wanted out. It was also true that I was still just in my twenties, and I wasn’t clear on much else, and I figured that I’d make the most of the ride while I could, especially since it was pretty clear that nobody was looking very closely at what I was doing. I liked feeling that I was getting away with something, and I took advantage of the ability to do so whenever I could, medium-wave surfing my corporate expense account with an constant excess of business travel, restaurant dining, drunken sex, and hotel high life, all of which felt like something while remaining entirely unfulfilling.

Strong cocktails were my drug of choice—Manhattans, at the time, in keeping with my frequent trips to New York, where  I made sure to schedule morning meetings for no earlier than ten or eleven, so that I had plenty of time to clear my head with a double espresso from my favorite little East Village Brazilian coffee window, or, if I wasn’t already running behind, a lingering breakfast at Cafe Mogador.

I’d been hired in October of ’96 to write code and manage the team of programmers who built everything that the digital side of Wired created—a slew of high-design ‘content’ sites including magazine-quality features on everything from travel and cocktails to health and romance, a full-fledged daily news site, as well as HotBot, which along with sites like Yahoo, Altavista, Lycos, and Infoseek, was one of the most successful search engines before Google came along.

Keep in mind that this was still early days for the web, before any kind of app store, and although now we all subscribe to and pay for all sorts of things online—and anyone looking back from the present would likely assume this would have always been the case—the fact is that at that point, nobody wanted to pay for anything online, and it was impossible to do so.

As we were developing these sites in ’97, ’98 and ’99, I know that we talked about the idea of charging users directly to access what we were building, but the idea was quickly and categorically abandoned as both technically insurmountable and also fundamentally opposed to the ethos of the early web, which is often summed up by something that granddaddy Stewart Brand said in a 1984 conversation with Steve Wozniak, the co-founder of Apple. Brand—now in his eighties and one of my neighbors here in Sausalito—is credited as having said that ‘information wants to be free’—pretty catchy, and also vague enough to mean almost anything at all.

It turns out that what Brand actually said was slightly different—that “information almost wants to be free,” and what he was getting at was that information was already tending towards being almost free, because the cost of distributing information via the internet was decreasing so fast that it was approaching zero. Said another way, the incremental cost of showing a web site to one more person is… just about nothing.

What he wasn’t saying was anything about the cost of creating web sites, nor about the value of information—neither of which, of course, are anything close to nothing. Computers and the internet do make it cheaper for more people to access—and create—information, but this truth got compounded along with Brand’s catch-phrase into what became the zeitgeist of those early days—the idea that, very broadly, everything on the web—even in the form of the highly articulated web sites that many of us were building, which of course required thousands of hours of work on the part of designers, software developers, journalists and many others—somehow ”wanted” to be “free,” and that users—that is, viewers, that is, people  like you and me—thought those sites should actually be free to access, forever, without any payment at all.

The history and consequences of this rather tragic misdirection have been spelled out in much greater detail by many others, most notably researcher and writer Jaron Lanier, who details precisely how the whole clusterfuck evolved into the present-day phenomenon of surveillance capitalism, wherein we trade for the rather pathetically false offer of “free” access to whatever-whatever.com the willy-nilly accumulation of mountains of data about our purchases, our relationships, our bodies, and every other aspect of our selves for sale to advertisers who use that data to try to sell us things we would otherwise never discover any need or desire for.

Back in the day, what happened was that since we wished for information to appear to be ”free,” we had to find someone other than the consumer to pay for it to be created. Unlike those of us who thought we’d cooked up something entirely new, advertisers knew exactly how to take advantage of this new flavor of what was to them a very familiar media business model. They were ready to pay, and they did so happily, especially knowing that lacking any form of direct payment or subscriptions, they would have all the leverage as the only underwriters of our work as publishers. The result for me was that although I went to work at Wired because it seemed like a cutting edge place to be with a lot of intelligent people and interesting technical challenges, I ended up working in advertising—a word that I still have a hard time saying without making an ugly face or feeling an painful twist in my stomach.

If I’d been paying any attention at all to myself and my own values, I would have felt the disconnect much more strongly, but I wasn’t, and so I didn’t gave much thought to the fact that my income was increasingly derived from something that, at the very least, I didn’t have any affinity for. In fact, if I’d been more in touch with what I really thought, even then I would have said that I hated advertising, but I didn’t slow down long enough see the big picture. I needed to make a living, and I’d ended up a new niche that I could occupy without much competition. I’m sure I share the experience with many thousands of other folks who took tech jobs because they were intellectually stimulating, only to realize much later how that was outweighed by the degree to which they were even more spiritually compromising.

We’d deluded ourselves with this fantasy of ”free.” It sure sounded sweet, but it was a lie from the start, and, ever the pioneer, Wired was the first to pollute their high-design creations with over-bright ad “banners”—online billboards blinking their messages, all doing their damnedest to redirect your attention from whatever it was that you were really there for in the first place. For the most part, I had my head so deep in programming and servers and gigabytes of logs and reports that I didn’t allow myself to consider how much I was put off by all of that shit—and again, there still really wasn’t any alternative, because—believe it or not—nobody had figured out how to do online subscriptions yet. Back in the beginning, we’d ruled out direct micro-payments because every credit card charge incurs a fee of something like twenty-five cents, but it’s still a mystery to me why someone didn’t come up with the idea of subscriptions at that point. It sure would have saved us all a lot of pain.

As final proof that I’d ended up in a direction that didn’t agree with me, I turned down two job offers in those years that I worked hard to negotiate, and that would have been interesting, and incredibly lucrative. Part of me still wants to kick the rest of myself for turning down the money, but at least I knew enough at some unconscious level not to go even further down that road. I may have been into some rather seamy stuff myself, but that all happened behind closed doors. As has become all too clear since then, large-scale programmatic advertising has done far more damage to society—a much dirtier business really, even than smut.

The truth is that even as I’d found myself inside and part of the fascinating machine of early tech wonders, the whole thing was already starting to make me sick, but I wasn’t listening to these messages. Instead, I felt uneasy, and confused. I cooked up those opportunities, and then turned them down. I earned a big promotion, and then realized that I didn’t want that either. I wanted out, but I didn’t know what else to do. If only I’d combined my interests in geography and software to create something like… Google Maps—but that didn’t occur to me.

What I did have, however, was a strong inclination to seek out other people with whom I had something in common, and also to strike out for relatively empty territory. I wanted to be known, and to be known for being different. As the early cohort of digital media companies of that era began to grow larger—CNet, Yahoo, Excite, AltaVista, The New York Times—I began to discover that there were other people who were doing similar work at the fast-paced, toxic leading edge of online advertising technology.

I went to a couple of conferences—and saw very quickly how downright terrible they were. The rules and regs of industry trade associations were never my thing, and neither were trade shows focused on advertising, which were, very predictably, super gross. I remember showing up for something called Ad Tech at the Moscone Center in San Francisco around that time, and I lasted about forty-five minutes before I felt like I had to puke. It was packed—and to this day, I cannot for the life of me understand why anyone would want to subject themselves to such a greasy free-for-all of soulless sales-floor hustle. Empty-eyed men in ill-fitting khakis roamed the aisles of pipe-and-drape booths, the whole scene freckled here-and-there with women in leotards printed with company logos half-heartedly putting themselves through the motions of R-rated pole dancer routines in front of small clusters of clones in the same pleated beige pants.

Jesus Fucking Christ.

There was one conference that I went to that was totally different, however. WebMonsters was a semi-secret group of tech wizards with a silly name and a very serious mission. You had to be jumped in by an existing member to join, and the ethos much more like an academic conference. Everyone there was nominally a competitor, but came together in the spirit of mutual assistance, solving deep technical problems, and building the internet at large.

It took me only a little while after that experience to realize that I could use that same model to start a group of my own with a focus that matched my own work more closely. Anyone who’s been indoctrinated in the lingo of 21st century entrepreneurship will have heard—and it’s true—that the best reason for starting a business is to ‘solve your own problem’—that is, to fulfill a need or desire that you discover within yourself, for which the solution doesn’t already exist.

I didn’t learn that axiom until years later, but that is in fact exactly what I did. Over the next several months I managed to pull together the first meeting of what would become this thing called AdMonsters. Strangely enough, and very much contrary to the idea that you have to have a ‘business plan’ when you start a business, I hadn’t even thought of what I was doing as a business at that point. I just wanted to meet and talk with other people who were doing the kind of work that I was, and I wanted to do that in a context that was interesting, engaging, and actually worthwhile on a personal as well as a professional basis. I wanted it to be fun, and possibly even cool—instead of the sick-to-my-stomach feeling of alienation that stuck to me for days after going to other conferences.

I was still working at Wired when we pulled off the first meeting. Although at the very beginning I was just one of several co-organizers, somehow I emerged as the leader once we were there together, and the group coalesced around the ethos that crystallized years later as “focus, quality, community.“ We were all competitors, but only five or ten percent of what we did was proprietary, and because everyone in the room had the same role in managing this emerging “ad operations” function within one still-nascent digital media company or another—a role that most other people had little to no understanding of, or sympathy for, we all felt a huge sense of relief and gratitude in suddenly being part of a group of other people that got what we did for a living. It felt like community, because it was, and my focus on serving that community, and on honesty, openness, and mutual benefit became the foundation that carried the business forward for the next fifteen years.

Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, the book-length memoir about a man learning to listen to himself, and the price I paid until I learned how to do that, serialized right here on Substack with a new chapter published every week.

You can find everything from the memoir that I’ve published so far right here.

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Further reading

Here’s the table on contents for the memoir. You might also enjoy some of my other work, such as

or any of the other essays that you can find here

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