Dropping out... kinda

How it happened

I was first pitched to drop out by my manager, midway through my internship. I instinctively shut the idea down, set on going back to school to finish my degree. However, after I really gave the idea some thought (and my manager badgered me about this some more), I became indecisive.

I figured the tradeoffs were as follows:

Pros:

• Arbitrage: I get to work a full year, heads down, at a pretty incredible and dominant startup before my peers even graduate. This means:
  • I get to make meaningful connections, potentially with people who could have a big impact on my career
  • It's easier for me to wake up each day feeling excited about the work I'm doing
  • I get to sharpen my skills and gain more experience building things quickly
• I'll learn faster how to live outside of the bubble of college and take care of myself
• and of course, I get paid a year earlier

Cons:

• I would potentially have to take a leave of absence from or drop out of school, likely forfeiting my degree
• I miss what would be my last year of college, including spending time with people my age who I like, learning within the structure of classes, and playing tennis (not to mention the captaincy of Brown's club team)
• I would be severing a lot of my relationships, and placing an enormous strain on the few that I could afford to keep

Doing some more thinking

Using this decision I was mulling over as a hook, I scheduled meetings with a bunch of cool people who I thought would have some insights. Very quickly, I learned that it's stupid to expect people, no matter how cracked or senior they are, to give personal advice without having a deep knowledge of your motivations. It's pretty hard to explain your thought process to someone you've basically never met in a 30 minute meeting. Even so, I think it was useful to hear the opinions of people you look up to and people who know what dropping out is really like, and it gave me a frame of reference to think about the tradeoffs of the decision in a more realistic way.

Using this frame of reference, I reasoned that the idea was sound — and from a completely different perspective, I was also drawn to the risk and thrill of the idea. By the time I started talking through things with friends and family, I was basically trying to dispel the arguments against leaving school. For example:

You'll never get your college years back, but you have decades to work; the same job will be waiting for you in 9 months

Elon Musk and Peter Thiel have both famously said something along the lines of "If you have a 10-year plan of how to get somewhere, you should ask: Why can't you do this in 6 months?"

Said another way, it is true I could have decades to work, but how long do I really have to be very dedicated to my goals? Will I still want or be able to do that in 5 or 10 years? Who knows? So yes, this job will still be waiting for me in 9 months, but 9 months is a significant time to wait (7.5% of 10 years), when the horizon is on the order of years, not decades.

You may never be in an environment again where it is so easy to meet and hang out with your peers

Definitely true when you first get to college. My thinking here is that since I already have more relationships with people that I'd be able to sustainably maintain post-college, I wouldn't be missing out too much — either way, come graduation, I'd have to let some relationships slowly wither. Leaving now would just be expediting that.

You can make progress along the same dimensions (i.e. making connections, being motivated, and sharpening skills) at school as you can at a company

Technically true, but I think personally it'll be a lot easier to do these things at a company, due to the fact that a) Brown doesn't have the same kinda start-upy culture as Stanford and b) that it's quite hard for me to focus in an environment with so many distractions.

It's stupid to not get your degree, you've already finished three out of the four years.

If the options were to finish school or to start work, I'd argue that this is a sunk cost fallacy — the opportunity cost of waiting another year seems really high.

Luckily, at Brown they're not mutually exclusive — Brown even offers a course (UNIV 1221) that provides two credits to students who want to work while completing their degree. With that in mind, yea, I agree it would be pretty stupid to not finish out my degree.

A lesson learned here is that at the end of the day, decisions this large are deeply personal, and need to be made independently. In retrospect, I should have written more about it to get more clarity.

Conclusion

As you can probably already tell, I ultimately decided to start work early, while finishing my degree at the same time. Before I move into NYC, I'm spending a week-and-a-half at school to savor the last bits of my college experience — playing lots of tennis, working on passion projects, spending time with people I care about, and catching up with buddies.

One thing I've found myself repeatedly having to do is to explain myself. Amusingly, people have really had a lot of mixed reactions, from enthusiastic congratulations to raised eyebrows. It's a good reminder—and maybe even a chip on my shoulder—to prove that the decision I'm making really is the right one.

If you find yourself in a similar position as I was this summer, I hope the story and the ideas I've shared about this process are helpful. Please reach out if you want to chat about it.