For most of my life, no one―myself included―ever dreamed that I would drop out of college. I was a good student, an Eagle Scout, the captain of the wrestling team…And for a long time, that was enough for me. I wasn’t looking for anything outside the desires of the typical high school student: a degree from a good college and a reasonably interesting, reasonably compensated job once I graduated.

Within that framework, I was doing great. But during my senior year of high school, something changed, and I no longer wanted to base my success on that model. I’m not sure what caused the shift in my thinking, but my cousins (and very close friends) Anneke and Jonah didn’t take the traditional route when they finished high school, and I think that opened my eyes to a wider range of possible lifestyles.

There were a few steps between realizing the traditional path might not be for me, and actually stepping off that path: I got into Northeastern University (2017), deferred for a year (2017-18), attended college for a year (2018-19), took a year off (2019), and decided to drop out in the middle of that year (winter 2019-20).

A taste of self-direction

Seeing Anneke and Jonah’s choices, along with a lot of privilege and extremely supportive parents, led me to defer from Northeastern for a year after I graduated high school in 2017. It was an exciting year – I fixed up and rode my 40-year-old motorcycle across the country by myself, spent 2 months with Jonah in Southeast Asia (my first time out of North America), and worked for a startup in Boston for a few months when I got home. Together, all those things changed me. It wasn’t any one experience, but rather the lessons I learned:

When shit happens, you can laugh or cry, but you have to deal with it either way…so you might as well laugh.

I had to push my motorcycle for a few very hilly miles near Yosemite when I destroyed my rear brake and broke my fuel filter in the same 10 minutes, when it was 95 degrees out.

I had a really high fever at a sketchy domestic airport in Indonesia, and kept falling asleep standing up while we were standing in line.

I got chased by feral dogs while riding a rented dirt bike in northern Thailand.

Did those things suck? Sure. But now I get to laugh about them, and knowing that I’ll laugh later made them much more tolerable in the moment. The sucky parts are often what make something memorable.

Despite the problems you’re facing, if you’re reading this, you’re probably better off than 99% of people on the planet. That doesn’t mean your problems aren’t problems―it just puts them in perspective.

I bombed an internship interview. It was really embarrassing at the time, and I was ashamed of my performance for a while. But you know what? It was good practice, and I still got a couple other interviews which led to offers. In the end, it didn’t matter much.

A plane ticket I had to buy cost 4x what I expected. Felt like a big deal at the time, but I didn’t care a week later.

I think that’s a good metric for whether something’s worth being upset about: if you won’t care in a week, why bother worrying now?

The things that seem out of reach probably aren’t.[[1]]

With maybe 1,000 miles of riding experience under my belt, I rode 7,500 miles on a motorcycle I fixed up myself, having never worked on a motorcycle before. Both the fixing and the riding seemed impossible at times, but it all worked out.

Indonesia and Thailand felt frighteningly different and distant…until I got there, and after two months surrounded by an utterly different culture, it didn’t feel so foreign.

And the idea that 18-year-old, man-bun-having, recent high school graduate me could get an internship at a startup in Boston, getting paid to do one of my favorite things (programming) felt like a pipe dream…and then through a combination of luck and tenacity, it worked out.

Back to the well-traveled path

After what had been the best year of my life, I returned to normalcy: I started at Northeastern in the fall of 2018. I’d always thought I wanted to live in the city, but my year off changed how I felt about that. I felt constrained by Boston’s concrete, and by my inability to find a place where there was no one around. The feeling that I could never be physically alone made me feel mentally alone. Being lonely while surrounded by people was worse than the loneliness I’d felt on my cross-country trip, because it felt like a personal failure instead of a product of my location (i.e., the middle of nowhere).

Despite meeting some great people, my first semester was the most unhappy I’ve ever been. I was doing well in my classes, but I felt like it was all busywork on the road to a degree that would qualify me to do more busywork. (I no longer entirely think that’s true, but it sure felt like it at the time.) All I could think about was the possibility of leaving.

At some point near the end of first semester I decided to take the following year off, and my life improved dramatically. Once there was an end in sight, college felt more manageable―I made some close friends second semester, and had some awesome times. But that was made possible by the certainty that the next year, I wouldn’t have to come back.

Take two on freedom

I moved out of my dorm after spring finals, and a few days later moved to New Hampshire for an internship with TomTom. But the road was still calling, so when the internship ended I headed cross-country on my motorcycle yet again. It was different than the first time, though: I wasn’t on such a shoestring budget, because I had work I could do from the road! That was when I started thinking I might be able to make my dreams work: go where I want, when I want, and do enjoyable work to support myself along the way. It felt like a miracle.

But it wasn’t, really. There was plenty of luck involved, but as one of my favorite sayings goes, luck favors the prepared. From when I was 12 or 13, I have spent a huge amount of my free time programming―and more recently, pursuing opportunities that allow me to do more programming. The full story of my journey from first typing print(“Hello, world!”) into a Python REPL to supporting myself by writing software will have to be another post, but here’s the short version.

After a couple years of doing countless Codecademy exercises, I stumbled into a mentorship at a small web development shop in my hometown. This was in 8th grade. I spent many afternoons hanging out there after school, and in the summer following 10th grade they offered me my first paid internship! The next summer, I sent somewhere between 50–100 cold emails to startups in Boston, and one (!) said yes. Throughout all this, I worked on countless little side projects, and tried to get school credit for programming in every way possible. After my third internship, I finally felt useful enough to start marketing myself as something other than an intern. That led me down a rabbit hole of blogs and internet communities dedicated to the pursuit of being a programmer-cum-entrepreneur, and that role is what I’ve been chasing ever since.

If you want to get paid to do what interests you, here are three concrete steps to take: 1) take responsibility for your own learning, 2) contact anyone in your field that you find interesting, and 3) learn how to market yourself. It won’t be fast, and you’ll get discouraged, but it will work eventually.

The six months after I left New Hampshire were a whirlwind. Two months on the road, a month in Alaska, more than a month in LA, two weeks in Hawaii, two months in Europe and Morocco…and scattered throughout were some massive wildfires, my first time skiing out west, my first real winter hiking trips, and to my amazement, lots of work coming my way.

For a couple years I’d had a sneaking suspicion that I might be able to live the life I wanted without finishing school, but those 6 months after leaving TomTom were when I really started believing it. In my head, I swung between dropping out or finishing school dozens of times, but kept returning to the same conclusion: if I went back, I would always wonder what would have happened if I hadn’t.

My final decision was prompted by the book Illusions, by Richard Bach. I don’t recall the specific passage, but I clearly remember sitting up in my hostel bed somewhere in Italy at 1am and thinking:

I’m not going back. If I went back to school, I’d be doing it because that’s what everyone expects. Life is too short to live by others’ expectations.

As cliched as it sounds, I felt lighter as soon as I made up my mind. I stopped agonizing over a decision I spent years thinking about.

The aftermath

Once I made a choice, I had to figure out how to communicate that choice in a way that people would be receptive to. This looks different depending on the audience, and it’s something I’m still working on. Here’s what works so far: with people my age, I just tell them I dropped out of school to be a software engineer, and they’re generally stoked. With older people, I often get a knee-jerk “don’t drop out of college!” reaction, so I add my reasoning:

While my decision not to return to school culminated in a single decisive moment, many things contributed to that decision. The biggest by far was that over the past few years, I’ve gotten more and more work doing something I enjoy, from wherever I want, on my own schedule. One lesson I mentioned earlier – that things which seem out of reach probably aren’t – is what made most of my professional success possible. I acted like I could get the work I was looking for, so I got it. Another big contributor to my decision was that as I fell deeper in love with the outdoors, Boston wasn’t where I wanted to be. As big cities go it’s one of my favorites, but it’s just too far from the mountains.

Once I made up my mind, I went all-in on building a consulting business. That meant finding leads. As an introvert, I haven’t had much success with traditional networking events. Instead, I read blogs and news sites like Hacker News, and anytime I come across an interesting post or comment, I email whoever wrote it.[[2]] It’s a form of “networking” that I really enjoy – I get to have interesting discussions with people who are way smarter than I am, and I sometimes get work out of it!

Dropping out of school has gone far better than I thought it would. I think that speaks as much to how the internet is making non-traditional careers possible, as to anything I did in particular.

What I’ve learned

To anyone who’s thinking about making a similar decision, I have some advice.

1. Whatever you plan to do after you drop out, make sure you’ve actually tried it before you drop out. If you want to be a writer, write your heart out and get some eyes on your writing. If you want to be a photographer, get to the point where you’re consistently getting paid to take photos before you drop everything else. And if you want to be a programmer, read and write as much code as you can, and solve problems for other people to get their attention. When working for yourself, actually doing the job is only half the work – the other half is marketing yourself. This is especially true at the beginning.
2. There’s a quote that’s something like: “It is better to regret what you did than to regret what you didn’t.” To you, what would feel more like “not doing” – not dropping out of school, or not having the college experience? That’s a decision only you can make.
3. Once you make a final decision, go all in. Don’t have a plan B. Don’t entertain the possibility that if things go poorly, you can go back to school, or reverse your decision. A plan B that’s less scary than plan A makes it too easy to bail when the going gets tough…which it will.

I’m most content when I’m fully responsible for my own future―both the good and the bad. If that resonates with you, I’m confident that you can make an unconventional path work for you too.

[[1]]: A couple years later, I read a good (and very weird) book that made me believe this even more: Prometheus Rising by Robert Anton Wilson. It persuaded me that our brains are very good at turning our beliefs into reality, and we can use that to our advantage.

[[2]]: I got the idea of non-traditional networking from Susan Cain’s Quiet: The Power of Introverts in a World That Can’t Stop Talking. That book changed my perception of my own introversion from mild shame to happy acceptance. I can’t recommend it enough.