Chapter 15 — Saved by a climbing gym, two real friends, kitesurfing, and a half-naked haircut.

An Ordinary Disaster — chapter 15 — Meeting the Mentor

The F250 that I owned at the time on a road trip to Baja. Note the bumper sticker.

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.

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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?

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?

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