I engineered my career to give me the adventurous life I always wanted

I found the right career by asking myself how I wanted to be spending my time.
I found the right career by asking myself how I wanted to be spending my time.
Image: AP Photo/Anna Johnson
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Two years ago, I was an associate at a high-powered law firm in Washington, DC. Now I own a chocolate company.

I wasn’t someone who’d always harbored secret dreams of pairing milk chocolate with roasted almonds, although it turns out I like that a lot. Instead, I decided to reverse-engineer my career to find a job that would give me the kind of life I wanted.

The perils of meta-unhappiness

I remember exactly when I decided to quit my law firm job. It was Memorial Day weekend in 2013. I was at a party on a Saturday night, thinking about some brief I was working on while the people around me laughed, danced and took swigs of bourbon. That’s when the terrible truth hit me: I was boring. And it was my time in big law that had sent me on a long, slow descent into dullness.

I didn’t hate my job itself. The people were smart and kind. The law firm paid me well and treated me nicely, with plenty of fancy lunches and free dinners. The work was even occasionally interesting. What I hated was the person my job was turning me into.

If I’d been miserable on a daily basis, it would have been easier to walk away. Instead, it was only when I stopped to think about how my life was playing out versus how I actually wanted to be spending my time that I knew something had to change.

I began to realize I had been asking myself the wrong questions for most of my life. Like many people I know, I always focused on the next steps: getting into college, landing internships, taking the LSATs, getting into law school, finding a job. The problem was that I was always working so hard to reach the next milestone that I never paused to consider whether I would be happy when I got there.

What I needed was a radical change in perspective. So I left my job and decided to embark on a year-long road trip.

Reevaluating my life

On August 31, 2013, I began the trip that would take me 40,000 miles around North America, mostly by myself. It was by far the most adventurous thing I had done in my life. And it worked—though not the way I expected.

I’d hoped I might have a “eureka” moment and realize what I should do with my life. That didn’t happen. I often wondered what the hell I was doing. I was so conditioned to worry about staying on track and setting myself up to succeed that it was hard to shake the feeling that this road trip was a horrible idea. And of course, I was haunted by the question of how this gap would look on my resume.

But as the miles ticked away, my perspective started to shift. Chatting for hours with bartenders in what’s left of small-town USA, narrowly avoiding multiple bear encounters, and finally seeing the Grand Canyon reminded me that there were a lot of people in the world I wanted to meet, a lot of things I wanted to do, and a lot of places I wanted to see. To my horror, I realized that the main obstacle to achieving these goals was time. And I had spent most of my time for the past six years flailing about trying to get somewhere I didn’t even want to be.

I emerged from the road trip determined to find the answers to two big questions: How do I want to spend my time? And whom do I want to spend it with? Once I knew that, I figured I could better align my life with my new worldview.

The problem with the “Work hard play hard” mindset

One of the most bizarre parts about going to law school is that you and most your friends go from starving students to well-off lawyers basically overnight. When I was working for the law firm, I was making enough money to do whatever recreational activities I wanted. I ate at the trendy new restaurants in DC, drank all the specialty cocktails I could handle, and never turned down the opportunity to show up an hour late to some concert as the loser still wearing business-casual attire.

I was living the classic “work hard play hard” lifestyle. But it turns out that’s a horribly inefficient way to get enjoyment out of life. Unless you truly love your job, the “work hard” part means you’re losing out on a lot of time when you could be doing something you care about. And the “play hard” part winds up feeling empty, because you’re trying to compensate for all that lost time.

Once I started focusing on the question of how I wanted to spend time, and with whom, the answers unfolded naturally. While I was on my road trip, a friend from college asked if I wanted to help him get some chocolate made as holiday gifts for our friends and family. Neither of us knew anything about chocolate. But we wanted to go to Nicaragua. It seemed like as good a reason as any to go explore the jungle down there.

I quickly fell in love with the world of chocolate. Not only does fine cacao grow almost exclusively in interesting and beautiful places like Vietnam and Madagascar, but the process of making chocolate is fascinatingly complex. The supply chains stretch all over the world, from some of the poorest and most remote regions to bustling trade capitals and on to highly industrialized manufacturing plants that look they could be making microchips and small shops churning out tiny batches of chocolate by hand. On top of that, the chocolate world is filled with the most interesting characters this side of “Best in Show.” The allure was impossible to resist.

A chocolate parachute

One year, two trips to Nicaragua, and a lot of chocolate later, I am a co-founder of MUCHOMAS Chocolate. My friend Derek, a former banker, and I started the company as a way to get chocolate made for our friends. We continue to run the business based on the philosophy that the people you meet are as important as the food you eat. Through our business, I’ve been able to spend my time more conscientiously, focusing on meeting interesting people and traveling to interesting places.

In the past year I have fully emerged from my boring law firm cocoon. I met Georg Bernardini, one of Europe’s most famous chocolate personalities, and played fetch with his dog on the banks of the Rhine. I met the Nicaraguan farmers who grow some of the best cacao in the world. And in a true “circle of life” moment, I drove cross-country again—this time armed with Georg’s encyclopedic chocolate book as a guide, meeting new friends in the industry on our way to the country’s biggest chocolate festival in Seattle.

When I quit my law firm job, the managing partner of the firm told me that sometimes you just have to jump out of the plane and hope that the parachute opens. A chocolate parachute doesn’t sound very aerodynamic. But it seems to be working for me so far.