Someone once mentioned that every life can be distilled into five major decisions—crucial moments when the choice determines our path until the next turning point. If that's true, one of my decisions occurred in 2015 in the far reaches of Washington State. At 33, I had just reached the summit of Mount Rainier, my first climb on a glaciated peak and the most adventurous thing I had ever done.
As the sun rose, I found myself in a small-town diner, wrapping my hands around a cup of coffee and contemplating the rainforest I planned to explore that day. My gaze drifted to the highway's long white lines beyond the window. Those lines could lead me anywhere—far from the Wall Street-adjacent law firm where I spent over 70 hours a week. Far from the endless screens and to-do lists that turned days into weeks and months. Far from the dissatisfaction saturating my life.
Seven years into my career, I had finally paid off my law school debt, was progressing toward partnership, and felt deeply unhappy. I liked the work, but representing financial institutions under government investigation didn't give my life meaning. It was merely a job—a good one, but just a job. I had made that job my entire life, prioritizing it over everything else, including my health and missing the birth of my sister's first child—a moment I could never reclaim.
In that small town, staring at the highway, I calculated how many nights of campsite fees would match one month's rent—240. It had been over a decade since I owned a car, and I had never camped alone. Yet, by the time my scrambled eggs arrived, I had decided to quit my job, move into a car, and live on the road, exploring America's wild landscapes.
Preparation for this new life took time. Over the next eight months, I quietly planned. In a box, I collected places I wanted to visit. In a spreadsheet, I budgeted for a year on the road, followed by another year of what I hoped would be rebuilding my life.
Beyond practical steps, I worked on embracing uncertainty. Since high school, I had followed a linear path—from college to law school to a law firm—and had long measured success with external metrics like salary and prestige. That rigid mindset stifled other parts of myself. What might happen if I let those parts grow?
Letting go of long-held beliefs, bolstered by a culture that values material wealth above all else, terrified me. A friend shared this piece of advice: follow what excites you, and you’ll be fine. That became my motto. I quit my job and set out on the road.
By April 2016, my one-bedroom apartment had been reduced to a used station wagon, and I was camping by the Colorado River in Utah. It was my first-night camping alone, and I barely slept. Around my head were "defense" tools: a flashlight, keys with a panic button, and another flashlight.
Despite being far out of my comfort zone and unsure of what I was doing, I continued, trusting I’d find my way. It turned out to be the best decision for me. Day by day, I figured things out. Soon I met others living out of their cars; I stopped surrounding myself with defense tools and slept better on the ground than anywhere else.
In the coming months, I opened up in new ways. I made friends at trailheads and on trails, went backpacking and rock climbing with them, and ran for miles in the wilderness with no watch or goal other than exploration.
I made plenty of mistakes. After rain diverted me on a run, I spent the night in a stranger’s car. These missteps taught me to trust uncertainty.
When I headed west, I had no itinerary other than one ambitious plan: to climb all the 14,000-foot peaks in Colorado. There are nearly 60. This goal silenced the nagging voice that whispered I was "wasting" time. By late July, I had abandoned the spreadsheet.
After spending a life checking boxes, I began to find a different sort of success by pursuing my curiosity and following my excitement. Eight years later, I no longer live in my car, haven't returned to law, and continue to chase what excites me. My life is now filled with purpose.
The gift of life on the road wasn't in the answers it provided but in teaching me to be comfortable with the questions.