I was sitting at the airport in wayward Detroit the other day, waiting for my early am flight to SF – on the way to start another new chapter. As I sat there thinking about what’s ahead, I was reminded that it’s been a year since I left Babson, the comfort of a traditional path through college, the often unary transfer of knowledge in the classroom, and a circle of close friends who I miss dearly. I’ve traveled tens of thousands of miles, lived in three major cities, worked with a number of brilliant people - some of whom I’m fortunate enough to call mentors, all of whom I’m beyond thankful to have met - and most importantly, have spent these twelve months learning more, personally and professionally, than I could have possibly imagined.
I took a series of calculated risks, often times without an expectation for a particular outcome.
Most of us take risks each day – sure, some are larger than others, but this habit is largely intrinsic to each and every one of us, even if we don’t make a conscious effort to recognize it. Most risks taken are done so with at least some thought given to tradeoffs and potential outcomes. But some aren’t. Some are calculated with very little to no thought given to an expected outcome. This is what differentiates a small minority of risk takers from the rest.
Some might think this is foolish - I would disagree. I argue that college is one of the lowest-risk environments we will ever find ourselves in – a point that affords us the luxury of not always knowing or caring about the expected outcome of a risk taken. This leads me to a conclusion:
I am returning to college in the fall as I will be able to effectively extend this comparatively low risk environment for one final year.
I was able to help start the Boston Startup School (now Startup Institute) in Boston, work with Passion Capital and their portfolio companies in London, and finally learn to code in San Francisco because I had a year’s worth of credit from AP courses and college coursework completed in high school (and because I was fortunate enough to have an overwhelmingly large amount of support from my family). Some would have studied abroad for a year – I just decided to take a few more risks than most. And I took those risks because I was still “in college.” In other words, if everything fell to shit, I could have returned to school, no harm no foul.
I’ve had a number of people ask why I’m even considering going back. And sure, I think it’s a valid question: with this much experience, especially with a burgeoning technical background that opens many more doors in the startup world, what value does finishing my final year at school hold?
So for the sake of argument, let’s assume I were to drop out. What would I do? I could build out a prototype of some product, maybe pitch it in front of a few folks, maybe raise a small angel round. Say I do that and six months down the road the product is a failure. Now what? Can I get hired at a startup? Maybe. I could also find a job at a startup. Cool – more learning, more experience. Say I do that, the company fails a year later or I want a change, and now I have to go job searching. Will I be judged for not having a college degree? Probably not, but is it worth the risk? Because remember, I’m no longer in the lowest-risk environment anymore – I gave that up to start a company or start work one year earlier. Is this trade off worth giving up a year of college? And as I’ll be making a major decision that could potentially keep me away from that low-risk environment, I can no longer rationalize taking major risks without carefully weighing the costs and expectations…
For me, it’s not worth it. I will return to school and take advantage of the lowest risk environment I will ever find myself in. I will continue to learn to code. I will continue to build out projects I find interesting. I will learn from these projects if they succeed, and I will learn from these projects if they fail. I will continue to write about my experiences. And most importantly, I will take the largest risks I can find, knowing that failure will result not in homelessness, but in knowledge.
I’ve talked about my sincere desire to learn selfishly – an even more exciting notion when you can take big risks – and I hope I can continue to glean knowledge in this manner back at Babson. I’m looking forward to spending my final year at school with friends, celebrating some milestones, and most importantly, learning as much as I possibly can so that when I do finish school, I will be in the best possible position to take risks while optimizing for success.