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How to live off the rails • Buttondown

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Obviously I’m kidding. First of all, like many of us, I was an idiot at 20. I had no idea what I wanted to do with the rest of my life, and I’d argue that at 20 that’s the correct call. Mostly, I wanted to do the next thing, and for me that turned out to be art school, which was a lot of fun, but not the sort of thing that points you towards “a career” as much as it gives you the space to explore what it means to be 20, which again—I’d argue is the correct call. I made some terrible art, took lots of drugs, pretending to enjoy boring films, made some relationship mistakes—again, the right time to do this—and racked up a little bit of student loan debt. (We’ll come back to this last point in a minute.) And sure, professors made some hand wavy gestures about art careers, which we kinda paid attention to, but the real message was clear: after this, you’re gonna have to figure out some other way to pay your rent, or—like us—you’re gonna luck into a teaching gig that allows you to teach the

June 5, 2025 How to live off the rails Sometimes you end up where you started. And that is beautiful. Enjoying the newsletter? Gimme $2 , you freak. This week’s question comes to us from Tyler Linton: Has your career played out the way you thought it would? Absolutely. Just like I drew it up at age 20. Obviously I’m kidding. First of all, like many of us, I was an idiot at 20. I had no idea what I wanted to do with the rest of my life, and I’d argue that at 20 that’s the correct call. Mostly, I wanted to do the next thing , and for me that turned out to be art school, which was a lot of fun, b

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