Someone once told me that every life comes down to five major decisions – five moments where the direction we take dictates the path we will take until the next moment. If true, I made one of these decisions in 2015 in the western parts of Washington State. I was 33 years old and had just climbed Mount Rainier, the first glacier I had ever climbed and the most adventurous thing I had ever done.
As the sun rose above the horizon, I sat down at a diner in a small town. Wrapping my hands around my coffee, I thought about the rainforest I planned to explore that day as my eyes looked out the window at the long white lines of the highway. These lines can take me anywhere. Anywhere was a far cry from the law firm at the end of Wall Street where I spent more than 70 hours a week. Away from the two computer screens and endless to-do lists that made days dissolve into weeks into months. Away from the discontent that pervades my life.
Almost seven years into my career, I had just paid off my law school debt, was about to partner, and deeply unhappy. Not that I didn’t enjoy the work. But the job—representing financial institutions under government investigation—didn’t give my life meaning. It was work—good work, but work. And I’ve worked all my life. I had prioritized it over everything else, including my health and most recently the birth of my sister’s first child. A moment I would never get back.
In that small town, staring out at the highway, I calculated how many nights of camping fees would equal one month’s rent—240. It had been over a decade since I’d owned a car, and I’d never camped alone. But by the time the scrambled eggs arrived, I had decided to quit my job, move into a car, and live on the road, exploring the wilds of America.
Preparing for my new life took some time
For the next eight months, I quietly prepared. In a box I collected the places I wanted to visit. In a spreadsheet, I determined what I would need for a year on the road, followed by another year of what I hoped would be a fresh start.
In addition to practical preparation steps, I also worked on becoming comfortable with uncertainty. I had followed a linear path since high school—college to law school to a law firm—and had long defined success by external markers like salary and prestige. This hardness was suffocating other parts of me. What if I give these parts room to grow?
Letting go of long-held notions reinforced by a culture that values material wealth above all else scared me.
A friend shared this advice: Go for what you’re passionate about and you’ll be fine. That became my motto. I left work and hit the road.
By April 2016, I had downsized from a one-bedroom apartment to a used van and pitched a tent along the Colorado River in Utah. It was the first night I was camping alone and I hardly slept. In an arc above my head were “defense” tools: a flashlight, panic button switches, and another flashlight.
Stepping out of my comfort zone, I had no idea what I was doing, but I kept going, kept believing I would figure it out.
This turned out to be the best solution for me
Day by day I figured it out. I soon met others who were living out of their cars. I soon stopped banging my head with protective gear. Soon I was sleeping better on dirt than anywhere else.
In the months that followed, I opened up in new ways. I made friends on trails and trails, went backpacking or rock climbing with those friends, and ran miles in the wild without a watch or any purpose other than exploration.
I made a lot of mistakes. After a storm surrounded me while I was running, I spent the night in a stranger’s car. Through these mistakes, I learned to believe in uncertainty.
When I drove west, I didn’t have an itinerary, but I stuck to a plan: In a spreadsheet I had mapped out how to climb every 14,000-foot peak in Colorado; there are almost 60. The target calmed the long voice telling me I was “wasting” time. If I climbed those mountains, just look how productive I would be. By the end of July, I had abandoned the spreadsheet.
After a life full of ticks, I began to find a different kind of success by pursuing curiosity and going for what excited me. Eight years later, I’m no longer living in my car, I haven’t gone back to law school, and I’m still pursuing what I’m passionate about—and still building a life of purpose.
The gift of living on the road wasn’t the answers it gave me, but how it taught me to be comfortable with the questions.