Chapter 17 — Learning that I didn't have to do it all myself
Chapter 17 — Learning that I didn't have to do it all myself
An Ordinary Disaster — chapter 17 — Joining Up
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.
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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
What does this bring up for you?
Have you ever started a business of your own?
What’s your experience with the endless fascination of travel?
What’s your experience with joining groups versus doing things on your own?
Where is the foundation of your own identity?
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