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Keep Your Identity Fluid


Gregorty Root '09
Gregorty Root '09

After a junior-year internship at a top investment bank, my professional trajectory was set. Finance was my future. 

At the time, I didn’t appreciate the extent to which my identity was already tied to that path. My family congratulated me on my prospects and my friends began approaching me about investment advice and tips for scoring jobs in finance. I even acquired the nickname “Goldman Greg.”

Then the financial crisis hit. 

And just like that, in the middle of my senior year, my “guaranteed” high-flying Wall Street career vanished in a puff of smoke. 

Unsure of what to do, I submitted a past-due application to a program called Princeton in Asia, which places college graduates in one-year social impact roles throughout Asia. Miraculously, I was accepted.

In stark contrast to the marbled lobbies of Wall Street, I spent my first year out of college in one of the most impoverished and remote regions of China. I taught English in a rural public school where the toilets were unplumbed, maggot-ridden trenches, and my shower was a rubber bag with a spigot, suspended from a rafter of my dorm room. A typical dinner was chicken liver and cubes of congealed pig’s blood.

The glamorous life of a financier this was not. Though I did acquire a few great stories. And it laid a strong foundation of resourcefulness and adaptability.

After my year in the hinterlands, the plan was to pivot back to finance. I’d dust off my suit and start stuffing dollars in my pocket. But evidently, fate didn’t get the memo. Every firm I applied to turned me down.

So instead, I spent the next three years in Beijing launching the fundraising department for the same non-profit I had taught for. 

During that time, we grew from five employees to eighty, becoming one of the largest and highest performing NPOs in China. In the process, I learned what it takes to rapidly scale an organization in a convoluted and unpredictable business environment.

While I didn’t make much money, the value of those unique experiences was profound.
Yet, in my head, I still needed the validation of a prestigious, high-paying job. That’s what everyone expected of me. It was who I was. Unable to shake that notion, I applied to business school.

Once again, I got lucky. Of all the schools I applied to, I was admitted to just one. And it happened to be one of the best. Surely, this was fate giving me another chance to claim my rightful place in the Wall Street boardroom.

In the first year of my MBA, I poured hundreds of hours into grueling interview prep for the all-important summer internship. I scored interviews with all of the top management consulting firms. Yet to my utter dismay, I was ultimately rejected by all of them.
At this point, I was mentally crushed. Here was my final chance to break into the big leagues, and once again, I had totally botched it. 

Something was clearly wrong.

In a fit of desperation, I booked a week of surfing lessons in the Dominican Republic to mentally reset. And as cliché as it sounds, a week out on the waves gave me the clarity I needed.

I realized I didn’t fit the mold these distinguished companies were looking for. And it occurred to me that every one of my successes, up to that point, materialized only after I rejected other people’s expectations of what I should do.

So once again, I pivoted.

I aborted my pursuit of prestigious, high-paying internships and instead fired off applications to fledgling tech startups where cookie-cutter molds don’t exist. 

My hit rate wasn’t great. But ultimately, I ended up securing a sales associate role paying a paltry $12/hour. 

No onsite chefs, no masseuses, no business class flights. Just a windowless, fluorescent-lit cave in the heart of Manhattan. But hey, at least this place had a flushing toilet.
My summer at that startup was transformative. 

Reporting directly to the founder, I rotated through every functional role in the company, learning more about operating a business than I would have ever learned in a traditional banking or consulting internship.

I continued to work remotely for that company during my second year of business school, and after graduation, I joined full-time as chief operating officer. 

In the three years that followed, we grew from three employees to 40, closed deals worth hundreds of millions of dollars, and ultimately, we were acquired by one of the largest players in our industry.

I now have the best job of my life working with my wife Mary Daphne (also a Hamilton graduate) on a variety of online educational initiatives ranging from professional social skills (Explearning) to personal finance (Stake Your Wealth).

And I’m happy to report that I’m no longer plagued by the desire to validate my self-worth through an esteemed, high-earning job. I’ve discovered that I’m far happier when I’m building things and challenging myself than when I’m seeking the respect of the people around me.

So if there’s anything you should take away from my story, it’s that there’s no “set” career path that you are shackled to. Don’t be afraid to let go of the reins and adopt a fluid, complex identity. Embrace spontaneous opportunities instead of forcing a future you think you deserve.

This approach can amount to much more than you might expect. And in fact, it is the ultimate manifestation of a true liberal arts education (hat tip to Hamilton).

My greatest failures emerged from attempts to conform to society’s model of success. My greatest victories came from venturing into the unknown, often to a chorus of warnings to “be sure you know what you’re doing.”

Well, I don’t know what I’m doing. Not really. And I’ve never been more comfortable with that fact.

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