Jumping into the void

a personal update

The Wanderer by Tanja Vetter

If you’ve talked to me in the past few years you’ve probably heard me say something like, man, I wish I had more time to read and write and meditate and understand the mind. Today I made this a reality: I quit my tech job after working there for three years with nothing lined up but free time.

It was a good run. I met incredible people, worked on things that I thought were useful. But eventually I got bored. And the stuff I was doing outside of work felt more and more interesting. That was the stuff that was really keeping me going—I didn’t wake up every day with a burning enthusiasm to ship code and attend stand-ups. So, that’s over now. I’m taking a few months away from the tech world to see where the little loves I’ve cultivated might take me.

I’ve never done something like this before. After high school it was always classes, internships, interviews, master’s, scrambling from one stepping stone to the next. Nowadays I meet all these people younger than me who are doing gap years or foregoing college altogether, carving out their own path, and I think: what a fucking awesome thing to do.

So I’m taking my belated gap year, I’m “dropping out” of the tech career ladder. At some point you run out of excuses (save more money, figure out immigration stuff, also these layoffs, also the uncertainty, and what if you just spiral, or what if you fail, blah blah blah). By the end it felt less like a decision and more like an inevitability: I am going to die one day, so I should not be spending hours and days and weeks and years doing things I don’t love to do. Agency—it’s a thing, you should look into it.

Having friends who are on a similar path helps. I’ve followed along on several “I’m quitting my job!” journeys now and it seems like a great use of time, whatever ends up coming of it. But I am also preparing for many moments of awkwardness and self-doubt. Parties: “What do you do?” “I’m…between things.” People generally find this exciting and cool, but you also hear the occasional “you’re doing WHAT? In THIS economy??”

Yes, in this economy. Yes, I don’t exactly have a plan—I have lots of ideas, but I have no idea where I will be in a year. Maybe I will be writing like a maniac, or trying to find some way to break into academia, or maybe I’ll just be at some other tech job.¹

In the past few months it’s dawned on me that the biggest impediment to my own success is my tendency to underestimate myself. It’s a fabulous coping mechanism: don’t set super high expectations, especially not in public, and you won’t have to deal with the sting of disappointment and embarrassment. I don’t even let myself imagine grand dreams of what’s possible for me, because once you’ve imagined it, supposedly, everything else will feel lame in comparison.

But that is not how the mind works. First of all, the mind doesn’t truly care about “success”; it just wants to feel loved and then it mistakenly assumes that that is what “success” will bring. Second, whether or not your life feels “lame” is really a matter of how earnestly you pay attention to the world, rather than how much “success” you’ve achieved. In other words: “success”, in the conventional sense, can be completely decoupled from your happiness, and so can failure.

So last night I dropped the resistance to having big dreams. I allowed myself to imagine: what are the most insane versions of success ahead of me? Publish a book? Not insane enough. Publish multiple best selling books? Nope, still timid. Publish the most widely read book of all time? Now we’re talking, let’s do that. Solve the hard problem of consciousness? Nice. Transform the social fabric of New York, America, and the world? On it. And attain Enlightenment while I’m at it? Perfect. Now, whatever happens, no matter how much I achieve, I will never be able to say “this is truly beyond my wildest dreams”. Instead I will say, with total contentment: “this is sick, thanks guys, but also my dreams were wilder than this, just sayin”.

It would be nice if the confidence and ambition could come to me more effortlessly. A lot of people describe me as calm and composed, but when I look at my own mind I see the complete opposite. If only I felt a deep self-assurance, no impulse to compare and feel jealous, no impulse to keep asking: am I doing this right, am I on the right path? But alas, that’s not where we are, and I’m not gonna let the doubts stop me from trying. I imagine that confidence comes, at least in part, from just doing things you would do if you were confident.

That’s really what I’m doing here: I’m acting as if I’m sure this is gonna work out, as if I, with whatever combination of talents and tenacity I have, actually have a great shot at making it all work, finding some path in the world that sustains me and also allows me to sink into what I love. Failure is an obvious possibility. But I can say I’m quite okay no matter what happens. Because—and I say this with the utmost seriousness—who gives a shit, really. I’m just some guy, trying to do his thing, just like everyone else who has ever lived.

1. A close friend said: “I wouldn’t be surprised if at the end of all this you decide your calling is web3.” Lol. Anything is possible I guess!