actually, everyone's life is weird

1. If you’re free and in San Francisco this Sunday (tomorrow!) at 11 AM and would like to hang out with other subscribers, please fill out this form. I prioritized paid subscribers so we currently have 75 people but I thought maybe we could aim for 100? I’ll close the Typeform when it’s full.

2. This year I’m the Fellowship Director of Admissions for Interact, a very special organization that (among other things!) organizes a twice-annual retreat for technologists ages 18-23. Interact and the people I’ve met through it have been a big influence on my life for many years. If you are an age 18-23 (rare exceptions made for 24-year-olds!) Bookbear Express reader and a technologist (our conception of technologist includes Internet writers, artists and thinkers so you may qualify even if you do not study CS or have a tech job) you should apply. Here’s the blog if you want to know more about some of the people who’ve been in Interact. If you’re over 23 or already in Interact but know someone who’d be a great fit, you should encourage them to apply :)

I was looking up a student club at Penn for an Interact thing when I remembered this guy, let’s call him F, who I had a crush on freshman year. He was a sophomore at the time, handsome and intimidatingly smart. It was one of those crushes I never made the slightest attempt to act on, since he had a girlfriend who looked like an indie movie star and I could tell he was a million times cooler than me. We barely talked but we’re still Facebook friends to this day, so I decided to check on his life. He’s now a medical resident at a prestigious program in the middle of the country, married to someone else who’s also a medical resident, and they have two cats.

I felt…. jealous? Because his life makes sense and my life does not make sense. I guess you could say that my life stopped making sense in a conventional way when I dropped out of college, but looking back it seems clear my original plan of graduating and working in finance was ill-conceived from the start. It’s not really about volition, or decisions, or anything like that. It’s about attention and where your attention naturally falls.

Most of my friends have life paths that go something like this: they got ruinously obsessed with something to the exclusion of everything else and then worked on it. And eventually that failed or succeeded and then they got ruinously obsessed with something else and started working on that. And it turns out that if you’re obsessive enough the credentials thing sort of goes away because people are just like, oh, you’re clearly competent and bizarrely knowledgeable about this thing you’re obsessed with, I want to help you work on it.

If you operate like this way you end up with a weird life because in a conventional career path there are all these rules and customs you’re supposed to follow, like you’re supposed to major in W in undergrad and get X internship and then go to Y for grad school and then work at Z. The truth is, most of the people I know are just too ADHD or impatient or unconventional to follow the path that’s expected of them. They may not have even been aware of what the “normal” thing to do was. And I’m certainly not recommending that or glamorizing it because rules and customs exist for a reason, they are necessarily useful. But it’s helpful to know that some people end up fine even when they don’t do the normal thing.

When I started writing full-time on Substack it was scary because the whole time I was in tech I told myself, okay, you’re trying to do this company but ultimately if it all goes sideways you can find a tech job and you’ll be fine. And the idea of fully committing myself to a creative career, a career as an Internet writer, was weird and frightening because okay, who is going to tell me what my life will look like? And what I can realistically expect and what I should be afraid of? How can I just live knowing that there’s no reassurance?

Something I wish someone had told me as a kid is that the only real “rule” for work is that you have to be able pay your rent and not hurt anyone and not break any laws. And within those confines you can do literally anything, hopefully something you find personally fulfilling. And the world is so wonderful and open and weird. I grew up in an environment where I was made to feel that if I got a single B+ on a report card nothing good would happen in my life because no colleges would accept me and then I would never get a FAANG job and I would die alone. Internalizing that logic helped me work hard but I also think it made me neurotic and fearful in ways that took a long time to undo. What I believe now is that if you’re creative and willing to work hard there’s a lot of different paths to success.

Reading history is useful partially because it makes you understand how varied people’s lives really are. The artists I admire have had lives that included nervous breakdowns and fleeing countries because of war and leaving their wife in another continent and writing their first novel to pay off gambling debts. That helps me remember that there is no such thing as a life that makes sense, or at least that’s not something I need to aspire to.

My parents grew up in China in the 1970s, in extremely difficult circumstances. They did not have enough food to eat throughout their entire childhoods. My mom’s entire family lived in an one-room house. Now they live in San Diego and work in IT and own a comfortably overweight dog. Now, I imagine that it’s pretty stressful to transcend the limitations of your impoverished rural upbringing and go to a good college and major in computer science in the late 1980s and then move literally across the world to Canada so your kids can have a good life only for one of those kids to turn around and say I’m gonna become an Internet writer. But actually my parents are great sports about the whole thing. They want me to be happy. And I think it’s because despite wanting stability and the guarantee of a comfortable future for me they know that everybody’s life is fundamentally pretty weird and there’s no guarantee of anything, for any of us. We’re all just trying to make it work in our own way.