Dive — a plea to take that big risk brewing in the back of your mind.

By the time I finally packed up my desk on the last day of work, there was only one sticky note left dangling from my center computer monitor — “Life is short.” I had spent 7 years at the firm, grinding towards the career I had always dreamed of, learning from peers I greatly admired, and finally, just when I felt I had “made it”, that’s when I decided to leave it all behind. As of last week, after what’s felt like a blink of an eye, it’s been one year since I left, and I can unabashedly say — best damn decision.

Since the age I legally could, I had an investment account. I’ve obsessed over the latest WSJ headline, been glued to CNBC, and concocted hair-brain options structures since I can remember. In college I co-founded an investing club, authored a stock blog, and used my earnings as a waiter for currency trading. If my memory was a little better I am sure I’ve seen the movie Wall Street enough to re-create the entire movie script, including stage directions. My friends would tell me they wished to know as well as I did what they wanted to do after graduation, and part of me enjoyed that. That part of me, however, was dead wrong.

Most people innately associate science with certainty, after all the field is centered around chasing objective truths. In reality though, science is not a black & white output, it’s a process, it’s trial and error, it’s hypothesis & testing, and it’s messier then your freshman year roomate. Ironically, it is exactly this messiness that allows us to arrive at conclusions in which we are confident, that we can be comfortable have been stress-tested, and that allow us to push our knowledge forward. If my final conclusion was to be a hedge fund analyst, where were the necessary experiments that backed up this belief, that would support me forging ahead when the going was tough?

There’s a reason pharma companies need to run trials with real subjects — no level of simulation could ever accurately predict the efficacy of a drug — just the same way no level of reading and watching could ever predict my fulfillment in a career path. To really discover your path, you need to discover yourself, and that takes getting down in the dirt, getting your hands dirty, exploring, failing, failing some more, and stumbling along until you truly find the footing that will make you happy. Leonardo DiCapprio didn’t hijack my frontal-cortex, implanting a seed of an idea that grew like a virus until I needed to hit eject, it was more like I had been sailing full-steam ahead for so long that I could no longer ignore all of that vast ocean I was laying to waste. It was time to dive in, it was time to jump.

Day after day we delve into our roles — whether it’s the role we play at work, at home, with our friends, online, or in our own head- and the more repetitive our routine, the more comfort we find in continuing down that path. The further down the path we go, and our perceptions become completely engulfed by this narrower and narrower reality we create for ourselves. That’s why one person can be ecstatic about moving into a 500 sq.ft. apartment, and another devasted when his Greenwich neighbor installs a larger tennis court in their yard, or why one day you might claim you put family above all else, and 5 years later you only see your children every other Sunday. We follow the norms of the culture surrounding us, and forget to ask ourselves what truly matters. Routine is the enemy of experimentation, and comfort is the enemy of perspective.

Thich Nhat Hanh writes “When you get into an argument with someone you love, please close your eyes and visiualize yourselves three hundred years from now. When you open your eyes, you will only want to take each other in your arms.” I think you could replace that “argument” with just about every contemplated life decision. Most people thought I was crazy leaving my job to pursue another passion, but really, did the downside they talked about really matter? My boss used to love saying — “let’s take a 30,000 foot view of the situation” — and maybe that is part of what makes him so successful; he is playing a different game then everyone else who’s dug into their bunkers, taking the facts as they’re bombarded by them. When I took that mental chopper ride up to 30,000 feet, the only true downside I could see was not taking the plunge, always asking what if, sticking with the comfortable option..

Which brings me back to my lonely sticky note — life is short. When my late father first saw the state my old job would leave me in, he would constantly tell me- just quit, you’ll figure something out. My head would explode as I explained how crazy he was, and that you can’t just veer off a path like that. Well, it may have taken me a few years to come around and heed his wisdom, but I finally realized who the crazy one was. Next time you’re worried about taking a big risk, remind yourself, life is short. Fighting with a friend about something that seems important now, but you probably wont care about tomorrow? Life is short. See an incoming call from that relative you don’t feel like picking up? Life is short.

Dedicate time to contemplating your values, asking yourself what truly matters to you, pursue your passion with dogged persistence, and above all, when it comes time for it — dive.

--

--

Brian Keenan
Digital Literacy for Decision Makers @ Columbia B-School

Founder at Odyssey. At: Columbia MBA. Was: HF Investor. Uncle. iMentor. Surfer. Reader. CFA. pursuing new ideas; seeking to make an impact.