Learning to explore (Part 1)

A little over a year ago, I sold every piece of furniture I owned in Boston, I packed what remained of my belongings into a rented Chevy Malibu, and I drove west.

For nearly 4 years, I had been the CEO of a start-up that I co-founded during business school. The company had grown to a point where I was no longer needed. And it was time for me to move on.

I had no idea what would come next.

2010 – 2020: how I first learned to explore

During college, I was laser-focused on getting a prestigious, stable, and highly-paid job. (Read: “The privilege to take a risk”)

Fortunately, I made it to Goldman Sachs. But within weeks of my start date, external recruiters began courting me, promising even better opportunities.

Anxiety gnawed at me.

As a 22-year-old kid, I didn’t know what I wanted to do. Like a hamster on a treadmill, I felt like I had been jumping through hoops all my life.

Yes I had jumped successfully, but a sense of unease kept slapping me in the face.

These hoops had always been created by others. Not me.

And right out of college, it was happening again — a 3rd party luring me inexorably toward the next golden hoop.

I was sick of following the conventional path. So in 2013, I left Goldman to work for a small hedge fund in San Francisco.

In San Francisco, there aren’t many hedge funds, so that by itself made my decision more unique. Plus, this smaller fund offered better work-life balance. So most importantly, it gave me room to figure out my own path.

At the time, the Bay Area start-up ecosystem was booming. I figured – why not try my hand at starting a company? I dove into several entrepreneurial projects in my evenings and weekends. Unfortunately, nothing came of those ventures, and after 3 years at the hedge fund, I left for business school in 2016 to continue exploring.

Early on during business school, I started a company that enjoyed some early traction. Thrilled, I charged ahead. (Read: $100,000 in Year 1 Revenue as Student Entrepreneurs)

4 years and several exhilarating wins, painful pivots, amicable founder break-ups, and exhausting near-bankruptcies later, I handed over the CEO reins and started my cross-country road trip.

July 2020: roadtrip, reflections, and a refresh

Westward I meandered — exploring parts of America that I’d never seen before. I climbed the hills of Pittsburgh, cruised the vast boulevards of Detroit, and peeked at Heisenberg’s house in Albuquerque.

Top left going clockwise: Pittsburgh, Detroit, Westcliffe, CO, Albuquerque

3.5 weeks later, I rolled into Los Angeles. It was the perfect city for me to settle for a while. I had a great living arrangement with a great friend. And I was now closer to my family in the Bay Area.

Prior to last summer, I had always operated within some kind of structure — an employer, grad school, or my own company. And I had the tendency to dive into things quickly — often too quickly.

This time would be different. There would be no institution to guide me, nor a playbook to follow. And for once in my life, I decided to take a slower, more methodical approach to my career.

Facing several months of unstructured exploration with no end in sight, anxiety — this time via an unfamiliar cause — gnawed at me yet again.

The good news is that I’ve learned to deal with that mental discomfort. Or rather I should say — I’m continuing to learn how to deal with it, and I feel like I’ve made considerable progress.

Next: Entrepreneurial reflections via exploration

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August 19th, 2021

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