How to live off the rails
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, 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 next generation of idiots for three days a week, and then take the train from Philadelphia back to your Manhattan loft and paint for the rest of the week.
Two things in that paragraph should jump out at you. One, I was able to do this and leave school with about $7k in student loan debt. Two, no fucking way an art school professor can afford a loft in Manhattan today. This was a different time. In fact, our art professors used to warn us that if we were planning to move to New York after graduating, we might have to get lofts in Brooklyn. Today, Philadelphia is filled with people who were priced out of Brooklyn. Time is not a flat circle, it’s a draining of the soul.
After art school I discovered that I could delay paying back my student loans by going to grad school, and while that added a bit to the debt overall, it turned a today problem into a tomorrow problem, which should be the defining problem-solving metric of anyone in their 20s. It also got me out of Philadelphia. I ended up going to grad school in Austin, Texas, still with some marginal idea that I was becoming an artist. And that’s exactly where I was when the web showed up, at which point the web turned into the next thing, and I got real interested in that. And because the easiest way to access the web at school was from within the design department, I started taking design classes.
It’s worth noting that the web, at that point in time (early 90s) wasn’t that far off from just being a weird new medium to make art in. And if you look around at some of the old people who’ve been working on the web for a while, you’re gonna find almost as many people with an arts background as with an engineering background. The web was wild back then. People did weird stuff. Some of it was great, some of it was terrible, and our relationship to pixels and code wasn’t that different from our relationship with paint and brushes.
Fun fact: the web did not stay this way!
Design was a fun new thing, and I enjoyed having a whole new thing to learn, so hurray. I eventually learned enough to get a crappy design job at a copy shop when I graduated from school, which turned into a less crappy design job at another company a couple of years later, and—boom—I ended up in San Francisco, which was still very much “the heart of the web” when I got here in 1999. I pogo-sticked around from job to job for a bit until I ended up starting my own design shop, from which I’m typing this in the year 2025. (A few things happened between 1999 and 2025, but they are mostly not worth mentioning.)
In addition to the main thread here, I also held down my share of crap jobs including washing dishes, newspaper delivery, landscaping, housepainter, working in a woodshop, disc duplication, sign painting, shipping, a short stint at UPS, and a couple I’m sure I’m forgetting. Not to mention, as the eldest child of immigrants, translation services, social services and data input from the age of eight.
So, back to your question—no, this is not how I drew it up at all.
I was lucky enough to grow up when decisions were cheap. School was still somewhat affordable, and perhaps more importantly—rents were still somewhat affordable. My first apartment in Austin was $100 a month. This was in 1991, which maybe feels like a very long time ago, but it really wasn’t. For context, the federal minimum wage in 1991 was $4.25. The federal minimum wage in 2025 is… $7.25. (Yes, I looked it up twice.) By that metric, that same apartment in Austin, if it’s still there and still a rental, should be less than $200. I guarantee you it’s not.
When decisions are cheap you can make a lot more of them. You can make do on a few shifts a week. You can take a week off from your shit job to go on a road trip to the airplane graveyard. You can rent a practice space for your band. You can get an art degree (or two!) that might not necessarily result in anything. You can chase this new weird web thing for a bit and see if it has legs.
I like to say that my career, such as it was, was built on curiosity. I kept my eyes and ears open to what was interesting to me at the time. And that is true. But it was also built on opportunity. Decisions were cheap. That’s no longer the case. It is much harder to take a week off from your shit job to go on a road trip to the airplane graveyard when your rent is $2000 a month and you’re sitting on a hundred grand in student debt. It’s even harder to take a week off from your shit job to go on a road trip to the airplane graveyard when your rent is $2000 a month, you’re sitting on a hundred grand in student debt, and your company is laying off 25% of the workforce because they believe they can replace you with a racist autocomplete script on meth and steroids, and chased by a glass of refreshing cooler from the Three Mile Island reactor. And of course, this being America, we have to add privilege to the mix because even though I’m an immigrant, I am an immigrant that passes, so whenever I needed a new shitty job, or even a new not-so-shitty job on the main design timeline, I walked into every interview looking like someone who should be considered.
My career also developed during a time of great newness. There’s no way I could’ve told my high school counselor that I wanted to be a web designer because that simply didn’t exist at the time. He would’ve laughed at me. (Instead, he laughed at me when I said I wanted to be an artist.) I was lucky enough to start my career just as the web was becoming a place where a career could be had, and because no one was trained to do web shit, it welcomed people with all sorts of close-enough skillsets. I took a risk, because I was able to. When decisions are cheap we can take risks that become almost impossible otherwise. And for a few decades the web grew exponentially, with a few hiccups here and there, until finally it crashed. This is where we are now.
Since the time when I started my career we’ve seen a collapse in opportunities. And a rise in exploitation. The cost of education (and we’re not even talking about what’s happening because of the current fascist regime) has skyrocketed to the point where a person like my 20-year-old self, who used a combination of small scholarships, loans, and workstudy to explore a curiosity about the liberal arts , and emerged with $7k in debt, simply couldn’t afford to go to school today. Not for that. Not for a degree that wasn’t on pre-set rails for a career. Not for a degree that didn’t give me a very high likelihood of walking right into a job where I could start at $100k/yr. Not if I’m carrying around a massive amount of student debt and expected to pay almost $2k for my share of a two-bedroom apartment.
Late stage capitalism, which has effectively pokévolved into authoritarianism, has destroyed the liberal arts.
Am I telling you not to go to college? No. Yes. Maybe? I am telling you that decisions are no longer as cheap as they used to be—and should be, honestly. We need 20 year olds to have the freedom to try things, the freedom to explore, the freedom to end up having careers that they couldn’t have imagined at 20. Life requires a certain amount of curiosity and exploration. Life is an open world game. It rewards you for exploring. And capitalism cannot fucking stand that. It wants you on rails. Capitalism wants you to earn the living that life has already granted you.
Am I telling you not to go to college? I am telling you not to get on the rails unless you’re absolutely sure that’s where you want to go. They have a destination, and if that’s the destination you’re sure you want, and if you’re absolutely positive you won’t change your mind? Hop on.
During the party scene in The Graduate, one of the neighbors famously gives Benjamin a piece of career advice: “Plastics!” Benjamin clearly isn’t interested in plastics as a career choice, mostly because Benjamin is lost. (And because it’s a soul-crushing suggestion.) There is a vague notion that he is expected to do something with his life, the achievement of which will be marked by expected outcomes. Spouse. Car. House. Golf clubs. Benjamin just needs to get on the career rail that takes him there. Why not plastics? At the end of the movie (I’m about to spoil a 58-year-old movie.) Benjamin and Elaine are sitting on the back of the bus, escaping their suburban life where plastics is a career possibility. We don’t know what their future holds because neither of them know what their future holds. They’ve jumped off the rails of their expected career trajectories. The camera slowly zooms in and we watch as the adrenaline fades and the fear sets in. They are terrified because nothing in their lives has ever prepared them for freedom.
Prepare your children for freedom. Living doesn’t need to be earned, but it does need to be fought for and defended.
Perhaps instead of asking children what they want to do with their lives, we should begin asking them what will make them happy in life. And be ready for that answer to change multiple times a day, as it should. And perhaps we should ask ourselves the same thing as we move through life. What would make me happy right now? Obviously, as we get older we pick up responsibilities along the way, and some of those responsibilities have names and desires of their own. And that is beautiful.
So maybe we’re not always gonna be able to take three weeks off work to take a road trip to see the airplane graveyard. At least not without bringing them with us. And you know what? That’s not bad.
Everyone deserves a road trip to the graveyards of capitalism.
🙋 Got a question you need me to answer? Ask it.
💰 Enjoying the newsletter? Gimme $2. Can’t afford $2? Keep enjoying the newsletter. Maybe send a nice email.
👕 Here’s a new stupid shirt you can cover your torso with.
🧺 …and a very cute enamel pin you can put on your backpack or jean jacket.
📣 June and July Presenting Workshops are now available and you should sign up.
🐀 No one has guessed the number yet, which is shocking.
🍉 Please donate to the Palestinian Children’s Relief Fund.