I engineered my career to give me the adventurous life I always wanted
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.
I didn’t hate my job itself. 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.
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.
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.