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The fall of my junior year, was my most difficult period in college. I took a semester off from school to work full-time in Brooklyn on a technology nonprofit I cared about, yet it was a lonely experience full of anxiety. By October, we only had two months of funding left, we realized what we wanted to build was much harder than what we first thought, and we had yet to arrive at a business model that would work, which we’re still solving. I didn’t know whether we’d be around in summer of 2017.
Despite believing enough in myself to take time off from school to work on a non-profit I cared about, I lost my self-confidence. So, I did what most juniors do in the fall. I looked for a summer job. I was interested in technology investing, and there were plenty of firms who posted jobs on our school’s career site, making the process of applying dangerously frictionless. In the end, I accepted an offer within a week of receiving it—like the rest of my friends.
Then something lucky happened. Our nonprofit got funded and I saw a path towards financial stability and growth. But I didn’t have the courage to back out of my offer even if I knew I loved my work in Brooklyn more. I didn’t follow the motto my roommate Andreas taught me, and I continue to repeat: “If it’s not a hell yes, it’s a no.” Ultimately, after seven uneasy months, I backed out in May to work full-time on my nonprofit for the summer.
I hesitate to give advice because I’ve barely had any life experiences and I have no idea how my choices will turn out. But here’s what the last two summers taught me about how to spend my time and avoid the pressure of pursuing certain paths.
All college summers are a risk-free shot at pursuing your passions. As much as I’d like to think it was risky to work on my own idea, it wasn’t. I knew that if my nonprofit didn’t work out this past summer, I would come back to college and everything would be fine. These chances are precious and shouldn’t be wasted.
The thing I hate to see the worst is when people in college have passions they don’t pursue. My brother, who just started his freshman year, told me a professor who spoke at his orientation told the audience: “Remember what you wrote on your college application. At least some of it must’ve been true.” Your college application is a great reference point.
If you don’t have an idea what you love doing, I don’t believe you. You’ve already been up for 16 hours a day for at least a few years of your adult life. Nobody knows for sure ever, but they can at least develop a hypothesis. That’s the best we can ever do: come up with hypotheses on the kind of work that makes us happy. Think hard about your hypotheses. Ask your friends and your family to help you out.
My advice is agnostic to specific industries. Ultimately, though, I do encourage people to expand the scope of potential options they think they have beyond the traditional big tech companies, consulting firms, and banks. These are great for people who love them, and I’ll never challenge a banking intern who tells me they enjoy M&A because I find it fascinating too. But based on how many people pursue these three routes, I’m sure that the number of people who go into them because it’s the path of least resistance is much higher than the number of people that go into them because it’s what they love.
Instead, I encourage people to consider a more entrepreneurial direction with their summers. This doesn’t mean I think everyone should go start a startup. To me, it means more people should consider less common opportunities.
Here is the strategy for finding a non-traditional opportunity that I like the most. It stems from a conversation I had with my friend Drew Bent. Pick a problem in the world you care about. That could be global warming, wealth inequality, underperforming schools, etc. Then find the top ten most interesting, accomplished, or promising organizations who are trying to solve that problem in some way. All big problems have organizations in the social, private, and public sector (not to mention academic researchers) working on them, so you’ll have breadth. Join the best one that gives you a job. If you can’t find a compelling organization, start solving the problem yourself and look hard for funding on campus (it’s often around).
If you spent sufficient time exploring these options, and you decide they’re not for you: excellent. I encourage people to explore nontraditional summer opportunities because I think the traditional opportunities face an unhealthy lack of competition from nontraditional opportunities, and college career centers facilitate this oligopoly. Not because one is better than the other. More choice is good.
I wish I had a friend who told me to think more critically about what else was out there. And I wish the college climate was one in which choosing non-traditional options was better respected. Sadly, it’s not, and that’s one reason why fewer people pursue them. There’s too much negative peer pressure out there, where we dismiss people who do things that are different as incapable of making it into the established routes.
Now what if you’re too afraid of taking a nontraditional route because you’re afraid of failing? For these people, I encourage you to think hard about what failing actually means. When you think critically, I’m confident you’ll realize failing is impossible because you have no responsibility or expectation. Say you pursue a nontraditional job and realize you don’t like the work. This can’t be called a failure for the same reason we don’t call people who go into traditional paths and realize they don’t like them failures. Anytime you figure out you don’t like something, that’s a win as long as you get away as soon as you can. Or say you start a summer project with the ambition of turning it into a company, and it doesn’t work out. Nobody expects you, a college student, to succeed in starting a company during a summer. This is a move with only upside. If creating a company doesn’t work out, you learned more than you could’ve hoped elsewhere, increased your chances of success for your next entrepreneurial goal, and became a more interesting person.
The scenario in which a fear of failure makes some sense to me is when people say: “I don’t want to pursue a nontraditional route because it may close down certain traditional job opportunities in the future.” If you’re diligent enough to think this far ahead, the probability is high that you’ll be able to get that traditional job later if you want it. Yes, some opportunities will be closed to you as a result of you not pursuing a certain path. But ask yourself why you even want to keep them open for yourself. Optionality is a dangerous drug. The risk of closing down a door you’ll likely never walk through is the price of discovering something you love.