Why I went back to college

Note: this was originally written ~August 2023.

Nine years ago, I dropped out of college to join a student retention startup. The irony is not lost on me. Today, I turn 27. I’m telling my story in hopes that someone like me is out there, feeling unsure of themselves, and seeking validation for the path they’re on.

Why I dropped out

My first year of college was mostly bad. I had been conditionally accepted to one of my dream schools, The University of Texas at Austin. All I needed to do to become a full, “real” UT student was to complete my first year co-enrolled at UT and ACC, the local community college. I allowed this minor roadbump turn in to the locus of my angst and resentment that lasted from the end of my senior year of high school until well past dropping out. I had worked so hard in high school to look good to colleges—I had near-perfect grades, became student body president, participated in clubs I hated, and even had a side hustle as a YouTuber.

Please keep in mind that I was a sheltered 17-year-old with a bit of an entitlement issue. I guess that’s just part of growing up.

Once I stepped foot on campus, my “co-enrollment complex” only grew. I didn’t make any new friends. I didn’t attend social gatherings. I didn’t make much of an effort in class. I started spending uncontrollably on my credit card to fill the void. More than likely, I had developed some form of depression.

But it wasn’t all bad. Being the enterprising young man that I was, I had been working a summer job at Upswing, an EdTech startup based in Austin. Once school started, offered me a part-time job in marketing. I happily accepted.

Working at Upswing gave me everything I felt I was missing at school. I made friends, had interesting work, and even got free lunch on Fridays. I would routinely skip class to head to the office and put in more hours.

As the first semester was winding down, I made a crucial mistake. I failed my favorite class, Physics, because I failed to study for the final or even show up for the review. I slept in instead.

One of the conditions to becoming a full-time UT student after my first year was to reach a certain GPA on a certain amount of classes. Since I had tanked my GPA, I was going to have to take 21 hours of courses and earn a perfect GPA my Spring semester in order to be elligible to complete the program. That didn't happen.

At the end of my Spring semester, returning to UT was no longer an option. However, Upswing had offered me a full-time job as the Marketing Lead. This would have been a tempting offer even had I had the option to return to UT. So I took the offer.

Shoutout to my parents for being so supportive. I knew they wanted me to attend college again, but I never felt pressured to return.

What it's like being on a "weird path"

Taking that job offer turned out to be an excellent decision. In the intervening years, I moved from marketing to product, and have spent the past several years as a Product Manager, a seemingly coveted job title (more on that later). By most measures, I was successful. By 24, I was making a six figure salary without a college degree.

While on this path, I found myself having to explain my decisions to people who thought I was on the wrong path. Larger family gatherings were often anticipated with a bit of anxiety, knowing that I was going to be asked, and perhaps lectured, about my collegiate career. These members of my family all meant well. Some of them had finished college well in to their 40s, and didn't wish the same for me. They came from a different world. So I understand where they were coming from.

But for anyone in this position: make your own choices. Own your decisions. Following someone else's advice is a great way to end up living someone else's life for them.

In The Pathless Path, Paul Millerd introduces the idea of the default path and the pathless path. We all know what the default path looks like. There's nothing wrong with it, either. It's a one-size-fits-most option. There's nothing wrong with the default path, in fact, I spent several years trying to get on it.

The pathless path comes with an ocean of uncertainty. Nights where you wonder if you made a huge mistake in trying something different. Days where you find yourself envious of the friends who got to experience the default. But those on the default path should have the same questions. Did they actively choose this life, or simply end up with it?

Why I'm coming back

After working in tech for several years, I'm returning to UT to complete my undergraduate degree. I'm not even in the exact major that I want, yet. I left behind a job as a Senior Product Manager making good money. Please, let me explain why.

  1. I don't like Product Management. Or at least, I didn't like what I was doing. I know that many, perhaps most, are in this boat. But I wanted to do something about it. I've always enjoyed solving engineering problems, but at work, I found myself mostly solving people, management, and budget problems.

  2. I want to get smarter. I'm taking several math courses, many of which I will undoubtedly forget and never use outside of the classroom. That's fine. I'm proving that I can do hard things. I'm creating new mental models. I'm expanding my intelligence.

  3. I'm finishing what I started. I've quit so many things. This is a big one. I promised my grandma I'd finish college.

  4. I want to be a student. When I first attended college, I was undeclared. I was just vibing and the vibes are bad. Having seen much more of the world and gathered a lot of data on what I enjoy working on, I have a much clearer idea of what I want to do, and how my college experience can get me there.