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The day I realized I was going against the career grain

4 min read

One of the most surreal professional experiences of my career was going to work for Medium. It was a decision I thought long and hard about, and was a sea change in the way I worked.

For my entire career, I'd gone against the grain. I bootstrapped an open source startup from Scotland, determined that I wouldn't move to Silicon Valley. I was the first employee at another one, based in Texas, that was determined to be Texan through and through. And then I finally founded a company in the San Francisco Bay Area, but was determined that it should be open source and decentralized (at a time when almost all investors were against the idea). In all these cases, while I had equity, I had a pretty low salary. In fact, I had never made much money at all, because I had put the highest priority on maintaining my social ideology.

So when I came to Medium, I immediately earned double the highest amount of money I'd ever made. Suddenly I was in this incredibly slick work environment, with empathetic, thoughtful people who were at the top of their skills. There were high-burn frills like kombucha on tap, but much more importantly, there were real benefits. Vacation was encouraged, there was parental leave, and I could spend thousands of dollars on my own education without drawing from my salary. (Side note: a lot of fancy tech company benefits are things that every employee in Europe is entitled to by law.)

Most strikingly, the people I worked with had mostly never worked in low-budget startups. If they'd been involved in small businesses at all, they had very quickly attracted millions of dollars in venture capital - but quite often, they'd come from companies like Google, and had enjoyed these kinds of salaries and benefits for their entire working lives.

Only then did I realize that for my entire career, by going against the grain and trying to build my own environments from scratch, I had made life incredibly hard for myself. Honestly, I thought that this was just how work was. But it turned out there was this world where, if I could accept not being my own boss and coming into an office building every day (which had both felt like psychological barriers, but in reality were very minor), I could make good money, go home at a normal time, take decent vacations without worrying so much about the budget, and be a healthier human being. What?!

In reality, I became incredibly anxious. Because I was working with people who had just had the luxury of focusing on their skills for their whole careers, I had really strong imposter syndrome. And everything was so slow, methodical, and ordered compared to the bouncing-off-the-walls chaos of an early-stage startup. I was still a little bit addicted to the adrenaline, and adapting was tougher than it should have been. This was the cushiest job I ever had, with some of the most genuinely amazing coworkers. I was a highly privileged technology worker, making really good money in a lovely environment - and I felt guilty for not being as happy as I felt I should have been.

Over time, it got easier. Matter offered me a job at the end of my first year, which I couldn't say no to. I think I wouldn't have done as well if I hadn't gone to Medium first: I had become a team player, and a much better employee. Had I stayed, I'm certain the unease would have continued to fade over time. I continued this growth trajectory at Matter; it was like losing an addiction to radical independence.

Honestly, I think that kind of radical independence is oversold. Being a founder - or frankly, even just a sole operator or consultant - is lonely, hard work, and the pay is bad. It's a bit sad that it took me over a decade to understand this. And while founding something is something I don't want to downplay, you should only do it if there's a foreseeable path to a point where you won't be in survival mode. (Real investment really helps, but it's not appropriate for every business, and not everyone can raise it.) Doing what regular people do - which is to get a job, potentially move to where the jobs are, pull a salary as part of a much larger organization, and build a financially stable future - is not at all a bad way to live. And I wish I could go back and tell me 25 year old self about it.