On proving yourself

11 April 2022
11 Apr 2022
New York, NY
6 mins

Since I began my research and prototyping sabbatical four months ago, I’ve had a lot of time to reflect on all of the factors that help me decide what I work on, and how. One of the things I’ve realized is that I used to be driven very much by a need I felt to prove myself – prove to myself that I could accomplish certain things I saw other people doing, and prove to other people that I met some certain standard I felt that I had to meet to be “interesting”.

Like any bright-eyed engineer fresh to the Valley, I wanted to start a company. I wanted lots of followers on Twitter. I wanted to be on the front page of Hacker News and Product Hunt. I wanted to have given a talk at a conference. I wanted friends who told me about all the cool, secret things big companies were working on, and friends who had money to angel invest or stories from when they were early at the unicorn startup du jour. It’s the stereotype, and it’s the butt of many, many great jokes on Twitter about the tech culture, but that only reveals to me just how pervasive this kind of — I don’t know, mindset? — is in the corner of the world I (and perhaps you) occupy. In short, there is always an in-group, and in the Valley, the climb to the in-group is steep.

I think I wanted these things because it seemed like successful people in tech, especially from engineering backgrounds, often followed these similar paths marked by these similar waypoints. In my mind, it naturally followed that if I could somehow unlock access to these rare emblems of skill and rigor and prestige for myself, the rest would soon follow.

A few years have passed since I wafted along the crests of waves of these feelings. These days, I find myself in a dramatically different working environment. I wake up every day, and get to begin my day by working on problems that are intellectually and creatively fascinating to me. I end many days thinking about conversations that I have with some of the smartest people in my field about what’s next. I do this work on my own schedule, free from fears of running hopelessly out of money or being stranded unemployable. I’ve also accomplished many of the things I chased after in those early years in tech. I’ve repeatably hit the top of the big orange site. I’ve launched projects that people have told me creatively and intellectually inspire them, and that hundreds of thousands of people use. I have the kinds of friends and network that I really wanted myself to have a few short years ago. Some of those earlier goals, like starting a venture-backed startup, have lost their glow a bit, but they’re still accessible to me, if I were to reach for them.

This was a gradual change that took place quietly in the background of my awareness. The first couple of times I was on Hacker News, this blog went from a tiny readership I could almost name off individually, to one of a hundred thousand people. After that summer, I remember distinctly thinking, “What if I never outdo this?” And I think that was the first time I became very conscious of how much this need to keep proving myself drove what I worked on, and how I pursued it. I wanted my work to remain relevant, and I wanted the dopamine rush of feeling like I was making cool and interesting things recognized by the community. It felt like I had taken the first couple solid steps climbing this ladder, and the fear that I would slip on the next rung and fall grew over time, until slowly I managed to convince myself that these weren’t isolated episodes of success, and that perhaps it could be true that people paid attention to my work simply because it was good.

The cliche response to this desire to prove yourself is probably something like “you don’t need to prove anything to the world; find your own passions and pursue them fearlessly.” But to me, that feels disingenuous. There’s no doubt chasing and ultimately reaching these waypoints dramatically improved my understanding and image of myself, my self-confidence, my career, the people I know and get to work with, and the way I imagine my future paths today. It would be hypocritical for me to say that it’s foolish to want to prove yourself, because feeling like you are qualified and worthy deeply influences how you do what you do, and if your work is a large part of your life, as it is mine, then it also deeply impacts how you see yourself, which then impacts all of the other corners of your personal life. It’s important to feel that what you create is meaningful, and in a noisy Internet, that requires getting attention. Getting attention – walking out into the metaphorical main streets of the net and yelling “look at this thing I made!” – feels pretty weird unless you’ve been playing the game for a while.

So, I don’t think you should just push these feelings away, if you feel like I used to. But feeling this way can still be uncomfortable, because it’s hard to know how to square these desires to be known and wanted and respected with our desires to work on whatever we want, however we want.

When I look back at my projects and writings that made the biggest impact in my career, they are never the ones that I built for the express purpose of accomplishing one of the many checkpoints I was naively chasing. Instead, they’re almost always borne out of me following through on what’s personally interesting to me: personal knowledge tools and search engines, programming languages and compilers, putting AI to work for creative humans. Of course, there is always the last 10% of the work of submitting a post to a forum or applying to give a talk. But I didn’t work on projects like Monocle or Ink hoping that this would be the project that would get lots of attention from people I respected. There were other projects I approached that way, and perhaps others are better than me at engineering luck, but that more direct approach never bore fruit for me.

It seems like smart people usually have good filters for noticing when people are creating something to satiate their personal curiosities or needs, and when a creation is a side effect of a fear of personal obsolescence. For me, it’s difficult to completely escape the desire to prove to myself that I can do harder and more interesting things. Even now, there are things that I’m not sure I’m capable of doing, but want to try. But fortunately I’ve found that just doing the thing that fulfills you the most also happens to be the fastest way to discover other people who will celebrate your ideas and hard work.

The conventional advice to hit arbitrary career goals like “get to know X person” or “get on Y website” is 10% just-doing-your-thing and 90% tactics, but I think the more fulfilling and effective path is 90% doing the work you would have wanted to do anyway, and filling in that 10% of tactics as opportunities present themselves to you. As you reach the checkpoints you’ve had in mind, let them build you up and help you be more ambitious, but don’t let them drag you blindly to those benchmarks.

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