Appreciating the uniquely delicious feeling of the last time

Extreme sports, sailing, intuition, fear, closing chapters consciously, and creating a relationship with death

A few months ago I was in the water out beyond the Golden Gate bridge, as I have been at least several hundred times over the past forty-plus years. I often call it all “sailing” for simplicity’s sake, but that day I was wing-foiling, riding a hand-built racing hydrofoil outside the Gate at over twenty miles per hour, gripping the sail directly in my hands and surfing the incoming ocean swell, jacked up against five knots of outbound ebb-tide current in the zone locals here call Himalayas.

I could feel every ethereal thread of a crisp northwest wind lashing down over the Marin headlands, its muscular sway and thrust compressed by the rocky gap spanned by the bridge to meet me there and press itself against the wing-like sail. Racing across the water I was aware of my tiny form set against the massive scale of the bridge, my hands miraculously able to tap into the mighty force of the wind, itself of an infinite scale even larger than any human construction.

Once launched from the beach at Crissy Field, I made my way upwind towards the bridge, dressed for heavy weather and well prepared by years of practice. I knew exactly where I was going—and yet, given the undeniable strength of the conditions in the water here, there’s no way to know exactly what I was getting myself into, or how I’d feel once I got there. Two thirds of the way across the bay I flashed past a triumphant sea lion with a salmon clamped between its jaws, my own teeth clenched against the elements as I worked to keep my feet planted on my board, the wind doing its best to tear me loose and send me sprawling with the sea life. One glance at the fresh orange flesh of the torn-open fish, and I returned my eyes to my goal, the nexus of the sailor’s world here in San Francisco Bay—the roiling center span of the Golden Gate.

Just a mile or so from the sunny green stretch of bayside lawn where we prepare our gear, the water beneath the bridge on a new-moon falling tide is a mess of saltwater rapids more than a mile wide—a million million tons of water pouring from all of California out into the sea—and on that late-March day with the wind blowing snot and the air and water both still below fifty-five degrees, I was shivering and half of my fingers were numb as I made my final tack upwind into the center of the channel. Going hand-to-hand with the elements and immersed in the most direct, powerful and dynamic states of nature, feeling the shape of the wind and waves in my muscles and skin, and hearing the whistling wind-song of the great bridge above as the river of tide froths white against the piers, navigating this tumbling of infinity in real time—and right here at home, close enough to turn and see the streets where I grew up—that’s exactly what I was there for.

I was in my element—and, then, after twenty minutes of survival sailing, as I felt another gust try to strip the sail from my cold and grasping hands, watching the land slide away sideways as the outgoing tide pulled me seawards, I noticed a feeling in my chest and belly, trying to make itself heard.

What I felt right then was not just cold and fatigue. I felt was fear—and I felt something else too.

It wasn’t so much the actual danger—although there was that, certainly. What I couldn’t ignore was an intense tension in my body, a tightness in my face and skull, and a tiredness that forced me to consider right then and there as I skimmed across the surface of the wind-blasted water—why was I there at all? Why do this to myself? and why do I do this to myself?

I know the answer. I do things like this because I can. I go out alone, in the strongest conditions and in one of the most challenging sailing venues in the world to feel my heart full in my throat, my pulse strong and my eyes wide and to feel my body move in instantaneous, continuous response to the relentless and ever-changing motion of this environment, so alive itself that to be immersed in that aliveness does, by force, make me feel that I too am alive.

When I’m out there I know exactly how that sea lion feels with a salmon in his mouth.

So feeling alive is why, and feeling alive is a good reason—and also, in that moment of frigid, thrumming aliveness, it became clear to me again and in a new and deeper way that it is my choice to be there, and that at some point I will choose not to got out there any longer.

At some point I will choose to make one day my last day out under the Golden Gate, just as I’ve already chosen my last time with many other things. I sold my motorcycles when I turned forty, and I gave away my last skateboard not long after that. I sold the business that I started in 2000 fifteen years later, in 2015, and I’ve never returned to that world. In early 2018 I chose to radically change my relationship with alcohol, and I won’t ever drink to excess again, or with any frequency or regularity. I spent thousands of hours over the past ten years becoming a competent cross-country paraglider pilot, and then one day last year, flying at six thousand feet above Mount Vaca here in the San Francisco Bay Area, I chose to go land, packed my glider, and made that my last day of paragliding.

This awareness of the last time has been growing in me lately. I felt it again just yesterday as I walked again towards the beach with my kite-foiling gear. It was a midsummer day on San Francisco Bay, and the fog hung low and grey, leaving a gap between the clouds and water lit silver and wan in the partial sunlight. Despite the gloom, the regular crowd of fellow sailors was on the scene, some already out in the water, some still chatting together by their cars and vans. I was wearing my trusty 4/3 wetsuit, a white hard-shell helmet that fits closely around my cheekbones, and a lightweight neoprene harness wrapped around my waist. The physical sensation of my tight and supportive superhero costume bolstered my confidence as I eyed the whitecapped surface of the Bay.

Crossing the beach as I approached the shore, I felt a clear and strong premonition that if I continued out into the water, that something would break. I’ve never had the experience before of asking my intuition a follow-up question, but this time I was actually able to pause and ask—would I break something of my equipment, or my own body? The clear answer was: broken gear—and at the moment that felt like enough for me to proceed. I reached the water line and walked in slowly, feeling the cold water permeate my suit, and soon I was flying across the water out near the bridge as usual.

An hour or so later I was riding back downwind, lining up the mark that would lead me to the beach, and I got thrown by a piece of chop, lost my balance, and fell forwards, planting my left knee square in the middle of my board. I heard a crunch, and came up to see that I had bashed several large cracks through the carbon-and-epoxy deck, leaving the inner core of foam exposed to the salt water.

My still-almost-new custom wingfoil board with its striped race-car paint job was ruined in an instant. My big yellow toy was broken! Momentarily dejected, I rode for another twenty minutes or so before returning to the beach. I felt sad and dumb and ashamed for having damaged a piece of very expensive gear that I had only just gotten from the shaper after a five-month wait—and I was disappointed in myself for not having acted on such a very clear premonition. Most importantly though, I felt relieved knowing I wouldn’t have to go out there anytime soon—at least not until I repaired that board.

As much as I love being out there, I felt relieved that I wouldn’t have to go back out in the water anytime soon. I felt relieved for not having to rig up and suit up and push off into the water. I felt relieved of the time and effort and the sand and cold, the sharp rocks on the path, and the risk of stepping in dog shit between parked cars. I felt relieved that I had only broken my board, and not my knee or leg or some other part of my no-longer-young body.

All of that—and—I felt relieved of the have to—the feeling that had pushed me to go out even when I’d been told very clearly that I was about to break something. I felt relieved of the pull that I feel when I hear the wind blowing in through the Gate on a sunny day. I felt relieved, if only temporarily, that I would have more time for other things some afternoons. It’s hard not to follow the urge to do something so powerfully elemental, and so rare, and so beautiful, in such a magnificent place, but I know from my experience with other things—and especially with addictions—when the thirst becomes a compulsion, it’s time for something to shift.

I had a laugh with my friends back on the beach, looking sideways at the beautiful board that I’d just crushed and split open, and then I packed up and drove home. I’ve had other close calls out there recently, and it could have just as easily been an injury instead of an equipment failure. My body was telling me to change my habit.

Outdoor sports have given me so much over the years. As it nets out, all of these sports, including this particular sport of wing-foiling, have given me a huge amount of energy, and I’m sure that this type of sailing still has more to give me. But right then, in the moment, I felt relief—and an awareness that the last time for something is approaching yet again. I’m still not ready to give up this sort of sailing, but I know this message well enough to pay close attention. The intuitive premonition that I had—and the subsequent fall, and the damage—was a reminder to only go out when I really want to, and also that the last time is coming. It may even already be close at hand.

We’re used to the idea that goodbyes are supposed to be sad, or at best, bittersweet. I’ve been paying attention to these last times though, and when I look back at my last hangover, my last time twisting the throttle on a motorcycle to push it past 100 on some back road north of the City, or the last time alone in my paraglider high up in the sky, I look back with love and reverence and respect and joy, and with no regret. I have no wistful desire to fly or ride or drink in that way again. I would love to fly in some other way, to ride bicycles or some sort of electric who-knows-what, or even to start another, very different business, but I have no desire to go back to past versions of myself.

It’s not just that I don’t want to go back. I have no desire to overstay my time in any particular chapter of my life. The feeling of turning the page at the right time is like knowing when to leave the party. You had a good time. Split before it gets ugly. Quit while you’re ahead. Move on down the road. Make space for something new. Let the message in about what’s coming next for you. It’s good-bye for a reason, after all.

I’ve come to love these moments of moving on, and as much as I resist the idea of giving up that feeling of holding the wind in my hands—or giving up the set of hot new bright-red sails that I just bought—I know from all of these experiences that it feels good to give up the holding on to something when it’s started to have a grip on me.

Many of these things that I’ve done to fight my way alive, to prove that I exist by going to the edges of the world and shoving myself up against them—many of these things I have gradually come to need and want to do less. I don’t need to have more of those experiences to have had them, or for them to remain part of me. I don’t need to keep practicing those parts of myself to be myself.

I want to press myself more into the center now, more into warmth, more into the sun. I have felt the edges and they are part of me, and I don’t need quite so much sharpness any longer. I want more soft glow. I’m making more space for slow. Giving up some of this gripping is allowing myself to be alive in other ways, to get older, to be mortal. My first-hand experience with strong substances and compulsive behaviors has given me an awareness of what addiction feels like, and so now whenever I begin to recognize those same feelings elsewhere in my life, I pause and consider whether something needs to change. Toko-Pa Turner wrote that “simply seeing a pattern is often enough to make it change. Once something is brought to consciousness, it can no longer operate covertly.”⁠ The opportunity then is to ask, how will I choose to respond to this pattern that I’m now aware of?

Giving something up feels a lot like freedom, and just as much as I’ve enjoyed the doing of something, in its time, I can enjoy the renouncing of it as well, when it’s time for that. As Peg O’Connor, author of Higher and Friendly Powers said in an podcast with Carl Erik Fisher, “When you renounce something, you put it down, and you say ‘this no longer has a hold on me; I no longer have an obligation to it…’ Renouncing something is an incredible kind of agency.”⁠ The moment of that last and final time that I do something has come to feel like a gift, or a plaque that I can hang on my wall and point to—a lifetime achievement award. Choosing to renounce is a conscious look towards the end—an acknowledgment and even, I’d say, a celebration—of death. Not to cut things short, but to say, I see you coming.

Every story has an end, and the final words are as important as the first.

To return to the moment where I began—what I saw right then, as a I flew down the face of a ten foot Pacific wave stacked up from the west and tilting ever-earthwards, is that I don’t need quite so much to scare myself alive. Looking back through the Gate towards the towers of the City, just hanging on by my toes—I felt my abs tighten and my back straighten up. My head lifted as I filled my chest with sea air, and I saw the last time coming.

a shot video shot by my friend Ben Anderson of me wing foiling on the wake of container ship NYK Orion as she comes in through San Francisco Bay ⬆️

Love reading?

You might enjoy some of my other writing on the subjects of sports, sailing, the body, fear, and death — in particular, how I was saved by a climbing gym, two real friends, kitesurfing, and a half-naked haircut, why I no nonger use psychedelics, a guerrilla mission to scale San Francisco’s most iconic landmark, why I no longer cringe at being called a "kitesurfer,” and how physical fitness supports my creativity and my work as a writer.

…stick around — I’ve got some questions for you…

1. Is there anything that find yourself doing that you also sometimes find yourself aware of not wanting to do any longer?

2. Are there any chapters of your life that you’ve chosen to close intentionally?

3. Are there any ways in which you are consciously creating a relationship with death?

4. What are some of the sports or activities that have been most important and enlightening for you, in your own life?

And finally, please let me know that you enjoyed this piece by clicking that cute little heart down below

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