This Is It

I was probably five or six years old the first time I thought I was going to die.

The exact context of what happened is fuzzy, as I was just a little kid, but I know I was at a friend’s house, and I know this friend had a pool in their backyard, and I know that one of the other kids swam up behind me and pulled me under just as I was trying to get out of the pool.

It was a playful, joking act. The kind of thing little boys do to each other all the time. But he had taken a deep breath before he submerged and I had not. After a handful of seconds I was stuck underwater, staring at the unreachable rim of the pool, completely out of breath. I flailed and scrambled but I had no air left, and my energy was sapped. I was well and truly screwed.

I remember clearly having what felt at the time like a very adult thought: This is it. This is how it ends. This is how I die.

It wasn’t the kind of thing I suspected I’d have to worry about for a while—or perhaps ever, since I was a kid and the concept of actual physical consequences for things wasn’t fully baked into my conception of the world.

At the last moment, as dark spots crept inward from the corners of my eyes, I popped back up to the surface like a cork. I scrambled up to the side of the pool and cried, looked for an adult to whom I could complain. And then swiftly forgot all about it. Most of it, anyway: that moment of uncomfortable clarity stuck with me, as did the newfound, death-inclusive worldview that it inspired.

I’ve been fortunate in the years since those halcyon days of swimming pools and roughhousing and forgettable contexts. There have been a few brushes with tragedy here and there, but nothing truly traumatic. Nothing personally debilitating or life-altering in a hugely negative way.

I have had reason to think those same words again, though in very different circumstances.

I started up my first business when I was in college, and there was a solid amount of fanfare surrounding its arrival in the local business ecosystem. The initial launch event felt like a milestone, to me, because it represented an extreme push into the unknown. I was testing the far expanses of my abilities, and my shuffling in what felt like the right direction somehow resulted in a product that didn’t totally suck and wasn’t widely reviled.

In retrospect, that same event now stands out as a high-point before a fall. The business hit its crescendo early, and I didn’t know enough or have enough experience to recognize it. My own ignorance of many things led to its collapse, that failure marked by an immensely hyped and wildly unsuccessful second event.

The night of that first event, though, when everything seemed to be going so well, and when I still had no inkling of what might come next, I thought those same words. “This is it.” This is a turning point of some kind. This is something important worth remembering. This could be a moment I look back on as the start of something wonderful.

That did turn out to be the case, in a way, though not in the sense I originally intended. That failure was an important moment of growth for me. It helped me recognize the value of many things I had taken for granted, and gave me the opportunity to stand back up under my own steam after taking a gut-punch.

There’s one more moment in which those words came to mind that, again, served as something of a turning point in my life.

Years after that failed experiment I was living in LA. I was on my third business, and this one was doing really well; way better than I could have hoped for, actually, considering the competition I was facing at the time in that market.

I had a client who had become something of a mentor to me, and who was offering me an opportunity to come into the fold—to work for him, to run some of his business interests, to make gobs of money, to have a certain kind of lifestyle.

I remember standing there in his office, looking around at the trappings of wealth with which he surrounded himself, thinking about all the people I’d met who worked for him and all the wealth-trappings they possessed and flaunted.

I also thought about how much stress I was dealing with pretty much all the time while working for him: the payoff was high, but the expectations and potential to mess things up were also amplified. Everyday things like getting stuck in traffic and struggling to get sleep and neglecting the gym for the third night in a row were wearing at me, physically and psychologically. Being stressed all the time was stressing me out.

“This is it,” I thought. I can see my future. I can see it all rolled out in front of me like a red carpet. A huge opportunity of the kind I’ve been hoping for since I got into business, became an entrepreneur. The big payoff. The next three decades or so, set in stone; chiseled into ridiculously expensive marble.

I remember the look that client gave me when I thanked him but turned him down. It was unthinkable that I would say no. It was such a sure thing, a gold-paved path.

That decision turned out to be perhaps the best one I ever made. It’s no coincidence that it was also one of the most difficult. There’s still a part of me that wonders how things might be different had I vastly more monetary wealth than time: the opposite of what I chose.

Part of what I love about my lifestyle today is that, although there are periodic whispers of that first story—moments where I wonder if I’ve stumbled into something dangerous, or even fatal—I experience plenty of the second: opportunities to challenge myself and face difficulties, emerging stronger on the other side.

And in the eight years since I started traveling, since that pivotable moment in LA, I’ve yet to be faced with a predictable future, one in which my entire story is visible, knowable, and set in stone.

This is a less traditional and often less comfortable path. But it’s also anything I choose to make of it.