Sailing is unlike almost any other activity, in that one does not come into sailing with apprehension and slowly graduate to comfort with experience. Just the opposite. Sailors who are really good, know everything about boats, and have thousands of hours at sea are continually and unshakably terrified while on the ocean. Not because they don't know what they're doing, but because they know the ocean so well as to fear it deeply, regardless of how conditions may initially appear. Novices, on the other hand, usually proceed with an affect which is considerably more blithe. As Brian Toss once said, there are only three types of sea-faring sailors — dead, novices, and pessimists. I knew this, but not well enough.

My friend Fritz and I had recently come into a small 15' hobie cat. We didn't really have a place to keep it, so we resolved to try anchoring it out. The idea being that we'd see whether we could set up a semi-permanent anchor mooring close to shore to keep it on, and then just paddle a windsurfing board out there every time we wanted to sail it. In the mean time we'd parked it, on top of a trailer, in a random Bayview side-street.

After work one day, we both hurried down to the boat launch with plans to get the hobiecat anchored out. We had two anchors, and the strategy was for me to sail the hobiecat out with one anchor, while Fritz would row the Sea Louse out with the other anchor. The sun was about an hour away from setting, and it seemed a little windy, but we were really only traveling 200 yards over to drop the anchor, and the wind didn't seem that terrible.

I sailed off the dock, around the pier, and into view of the anchor spot. As soon as I came out from behind the protection of the pier, I was hit with the full force of the wind, and realized for the first time that it was probably blowing a strong 20 to 25 knots. The hobiecat was incredibly light, and was moving amazingly fast, but was also fairly difficult to maneuver in those conditions. I immediately realized that the wind was too strong for our operation, and decided to head back to intercept Fritz.

I had mis-rigged part of the hobiecat, and as a result it took me a while to get it turned around. Before I could head back, Fritz came rowing around the pier, was suddenly hit by the entire strength of the wind, and was blown out into the bay. I sailed past him and suggested that we should just head back, but he was having trouble rowing steadily, and after a few more passes, it was clear that he wasn't making much headway. I began to get worried that the sun would set, that he'd get blown out into the bay in the dark, and that nobody would be able to find him since he didn't have a light.

The wind was howling relentlessly, and the sun was already nudging below the horizon. Seeing that things were beginning to get serious, I tacked over with the intention of picking Fritz up and either towing or abandoning the Sea Louse. As I was shifting my weight over from the tack, a huge gust of wind hit the boat and instantly capsized it. The suddenness of it was unbelievable, as if I was on a tiny model made of paper which someone had simply flicked with their finger; I didn't even have time to register that it was happening. I landed in the water, felt the shock of intense cold run through my system, and gasped as I clambered onto one of the overturned hulls. The wind was blowing so hard that it effectively pinned the boat down, preventing me from righting it, and eventually turtling it completely.

In disbelief, I took stock of where this simple operation — moving a small boat 200 yards — had left me. My phone was dead from the initial water impact, I could see Fritz way off in the distance but didn't know if he could see me, there were no other boats out on the water, no other people on shore, and the last bit of twilight was beginning to fade. I had a life jacket, but was wearing soaked cotton clothing and had no light or radio. Even if there had been anyone around, yelling would have been useless, as the wind would have immediately scattered my cries.

I looked in the direction I was being blown, with the vague hope that I'd end up somewhere reasonable. I wasn't drifting across towards the Oakland side of the bay, but both out and down towards the south. I tried to do the math. I was pretty wet, and in those temperatures, knew that it wouldn't be long before that started to effect my ability to function. I didn't know if or when Fritz would call for help, if he'd even make it back himself, or whether anyone would find me in the dark.

The severity (and stupidity) of my situation was not lost on me. Like anyone, I'd occasionally seen stories about people who drowned in the bay, or succumbed to hypothermia on a local hike. I had always wondered how those kinds of things had been possible, and I realized that this was exactly how it happened. A series of small mistakes and bad decisions left the people in those stories exactly where I was: drifting through freezing water in the dark. I knew very well that in 50 degree water I had 30 to 60 minutes before I lost consciousness from hypothermia.

There was a pier a few thousand yards upwind of me. I looked back downwind, and again contemplated the absolute inky darkness of my current trajectory. How long would I make it before hypothermia? Probably not long enough, it occurred to me. Should I try swimming to the pier? Every second I hesitated brought me slightly further from it. I noticed that I'd already started shivering.

Time passed, and it became clear that there were no other boats on the water, much less a boat that would actually see me. I decided swimming to the pier was the last option that I had any agency over. My only other option was to float with my partially submerged vessel and hope that someone found me before hypothermia did, but my hope of that had largely faded with the sunset. I reasoned that if I tried swimming for it, but didn't make it and became separated from the boat, I'd be well on my way to dead within minutes for sure. So as a precaution, I resolved to swim directly upwind from the boat, such that I'd have a better chance of floating back downwind to be reunited with it.

The bay is ice cold, and even though I was partially submerged, sliding all the way off the hull of the boat was so overwhelmingly frigid that it knocked the wind out of me. I started swimming upwind towards the lights of the pier, still wearing my life jacket and all of my clothing. The wind-waves kept hitting me in the face, and I swallowed a lot of water. I'm a strong swimmer and grew up swimming competitively, but it's only possible to swim through the cold for so long before your body shuts down. After 20 minutes, my boat was quite a ways downwind of me, but the pier didn't appear much closer.

I took stock again. The same wind which had capsized my boat was still whipping over the water. The cold had sapped my strength, I was having difficulty continuing to move my arms, and I realized that I wasn't going to make it to the pier. Floating alone in the dark, with the icy waves washing over my head in that utterly relentless way that is specific to the ocean, I felt the hypothermia really start to set in, and realized that I was probably going to die. I was mostly overwhelmed by the sheer stupidity of it. After all the impossible single-handed passages I had made, all of the freight trains that I'd ridden through freezing nights, all the times that I'd found myself in dangerous situations, been shot at, or embarked on obviously dangerous projects, it seemed absurd that I was going to drown a mere 3,000 yards away from the shore; the final result of what should have been a simple 10 minute operation.

There was also the slowness of it. It wasn't as if I had been shot with a bullet or hit by a bus, suddenly dead. This was something completely different: a slow, inevitable, and extremely lonely series of events that I was being dragged through over the course of an hour. It was strange to think that these were all moments which nobody else would ever know about. I shuddered with the thought of Jim Gray or Joshua Slocum, both people I admired who were lost at sea, and realized that they each must have had their moments like this one. All alone with the inhospitable and uncaring ocean, slowly undergoing the realization that this was it.

The pier clearly out of my reach and the hypothermia clock ticking, I decided to try making it back to the boat. Although I'd been swimming directly upwind, the boat was some ways off from directly downwind of me. I realized that the underwater sail was probably catching the current from the ebbing tide, moving it horizontally away from me. As I swam and drifted back towards it, it became clear that I would very likely end up missing it. I knew that if I got blown downwind of it, I'd never be able to reach it again, and that this was my last chance to catch it.

Strangely, I could feel myself drawn towards the temptation of giving up, even though I knew failure meant certain death. In hindsight, I think it's because the act of giving up feels so similar to the sensation of success, at least in a superficially immediate way. I had been imagining making it to the pier, and had pictured the sense of release that I'd experience when collapsing on dry land. Giving up bears a deceptive resemblance, in that it offers a similar sense of release which comes with letting go and ceasing to try. I had to remind myself that they're not the same.

I looked again at my trajectory in relation to the boat, and realized that it was now or never. I knew that my life was at stake, and that I had to summon every ounce of my strength in order to make one final sprint towards the boat. I gave it everything I had, moving my arms in the general form that I knew one made while swimming, even though I could no longer feel them or sense that they were actually propelling me through the water. I looked up just as I was drifting past the stern of the boat, reached out at the very last second, and barely caught hold of a small bit of line that was trailing off the submerged rudder.

I pulled myself onto the hull again, almost vomited, and noticed that I was starting to get tunnel vision, presumably on the path to blacking out completely. My body was shivering hard, but I knew that I was slightly better off with the boat than I was floating freely. I realized that now, without a doubt, there was nothing else I could do. I continued to marvel at and be frustrated by the stupidity of it all. I wondered how long it would be before I blacked out, and how much longer before my heart would stop.

Time passed, and even though my thoughts were now coming slowly, I started trying to work through questions of how I should position myself such that I wouldn't be face down in the water when I blacked out. I tied a line around my wrist so that I would stay with the boat wreckage once I was no longer conscious.

My vision was hazy, but through the darkness, I saw the mast-head light for a moored tugboat flash on. Then its running lights came on. I knew that I was probably invisible, but this was the first other vessel I had seen during the whole time I'd been out, and suddenly it felt like I had a chance again. Even though they were upwind of me, I screamed as loudly as I could, which turned out to be not much more than a dull moan. I tried to wave my unresponsive arms. They started heading in my direction, and I summoned everything I had in order to lift my arms up, knowing that they could easily just pass right by me or even run me over without ever even noticing.

Against all odds, they happened to see me.

Getting me out of the water was another 15 minute process, since I was nearly-dead weight and wasn't much use. When they'd finally gotten a rope under my arms and were pulling me up the side of the boat, I got wedged in the row of tires that typically line a tug. All I needed to do was put my leg out and push off from the side of the boat's hull, but I couldn't do it.

I was so far gone that I never really saw the name of the boat or the faces of my rescuers. I only remember the floor of the engine room, where they carried me to be near the heat of the engine. Eventually I ended up in a hospital, where I was heated until I stopped shaking and regained full consciousness. When they brought me in my core temperature was so low that the digital thermometers wouldn't register it.

And now I'm fine, with only a few bruises and some rope burn. But the past few days have been colored by the knowledge that I shouldn't be alive. There was absolutely no reason for that tug to have seen me, and just dumb luck that it was there at all. It's strange to think that I really should have died out there, and that all of this should be happening without me. I don't know what I'll do now, but I do know that I have re-learned my fear of the ocean, and that there's no such thing as a "short trip."

(Fritz made it back without incident, had no idea that I was in trouble, and was hours away from calling anyone.)