Someone once told me that life can be summed up in five big decisions — five moments in time when the direction we take determines the path we take to the next juncture. If that’s true, I made one of those decisions in Western Washington in 2015. I was 33 years old and had just summited Mount Rainier. It was my first glacial peak and the most adventurous thing I’d ever done.
I was sitting in a small-town diner as the sun rose over the horizon. Hands crammed around my coffee, I stared out the window at the long white line of the highway, thinking about the rainforest I would explore that day. That white line could take me anywhere. And anywhere, far from the law firm on the edge of Wall Street where I spend 70-plus hours a week; far from the two computer screens and never-ending to-do lists that melt into days and weeks and months; far from the dissatisfaction that permeates my life.
Nearly seven years into my career, I’d paid off my law school tuition, was on track to become partner, and I was deeply unhappy. It’s not that I didn’t enjoy my work; but my job, representing financial institutions under government investigation, didn’t give my life meaning. It was a job. It was a good job, but it was just a job. And I’d dedicated my life to it, prioritizing it over everything else, including my own health and, most recently, the birth of my sister’s first child. It’s a moment I’ll never get back.
As I stood there, staring out at the highway, I calculated how many nights at the campground would cost in a month’s rent: 240 nights. I hadn’t owned a car for over a decade, and I’d never gone camping alone. But by the time the scrambled eggs arrived, I’d decided to quit my job, get in my car, and live on the road, exploring the American wilderness.
It took time to prepare for a new life
Over the next eight months, I quietly prepared. I filled boxes with places I wanted to visit. I filled spreadsheets with budgets for a year of travel, and then a year for a fresh start.
Beyond the practical steps of preparation, I also worked on getting comfortable with uncertainty. Since high school, I’d been on a linear path: college, law school, law firm. And for the longest time, I’d defined success by external metrics like salary and prestige. That rigidity held other parts of me back. What if I gave those parts room to grow?
It was scary for me to let go of long-held beliefs reinforced by a culture that values material wealth above all else.
A friend of mine gave me this advice: “Just go and do something that excites you.” That became my motto. I quit my job and started traveling.
By April 2016, I had moved from my studio apartment to a used station wagon and was pitching a tent along the Colorado River in Utah. The first night I camped alone, I barely slept. I had an arc of my “defense” tools above my head: a flashlight, a lock with a panic button, and another flashlight.
I was out of my comfort zone and had no idea what I was doing, but I kept going, believing that I could make it work.
It was the best decision for me
Day by day, I began to understand more. Eventually, I met other people who were living in their cars. Eventually, I stopped shaving my head with protective gear. Eventually, I started to sleep better on the ground than anywhere else.
Over the next few months, I opened myself up in new ways: I made friends at trailheads and on the trails, went backpacking and rock climbing with them, and ran miles into nature without a watch or any other goal other than to explore.
I made a lot of mistakes—I got lost mid-run in a storm, then spent the night in a stranger’s car—and through those mistakes I learned to trust uncertainty.
On my way out west, I didn’t have a set itinerary, but I did stick to one plan: a spreadsheet with instructions on how to climb every mountain in Colorado above 14,000 feet. There are nearly 60 of them. This goal silenced the voices that told me I was “wasting” my time. Think about how productive I’d be if I climbed those mountains. By late July, I abandoned the spreadsheet.
After a life of checking boxes, I began to find a different kind of success by following my curiosity and doing what excited me. Eight years later, I’m no longer living in my car or back in law, but I’m still pursuing what excites me and building a life full of purpose.
The gift of living on the streets wasn’t that it gave me the answers, but that it taught me to be comfortable with questions.
