Someone once told me every life boils down to five major decisions —five moments when the direction we step dictates the path we’ll travel until the next juncture. If it’s true, I made one of those decisions in 2015 in the western reaches of Washington State. I was 33 years old and had just summitted Mount Rainier, the first glaciated peak I’d ever climbed and the most adventurous thing I’d ever done.
As the sun crested the horizon, I sat 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 toward the highway’s long white lines. Those lines could take me anywhere. Anywhere was a long way from the law firm at the edge of Wall Street, where I spent 70-plus hours a week. A long way from the two computer screens and never-ending to-do lists that dissolved days into weeks into months. A long way from the discontent permeating my life.
Almost seven years into my career, I’d just paid off my law school debt, was on track for partnership, and was deeply unhappy. It wasn’t that I didn’t enjoy the work. But the work — representing financial institutions being investigated by the government — didn’t give my life meaning. It was a job — a good job, but a job. And I’d made that job my entire life. I’d prioritized it over all else, including my health and, most recently, the birth of my sister’s first child. A moment I’d never get back.
In that small town, gazing at the highway, I calculated how many nights of campsite fees would equal one month’s rent — 240. It’d been over a decade since I owned a car, and I’d never camped alone. But by the time the scrambled eggs arrived, I’d decided to quit my job, move into a car, and live on the road, exploring America’s wild places.
Preparation for my new life took some time
Over the next eight months, I quietly prepared. In a box, I collected places I wanted to visit. In a spreadsheet, I budgeted what I’d need for a year on the road, followed by another year of what I hoped would be starting anew.
Beyond the practical preparation steps, I also worked on getting comfortable with uncertainty. Since high school, I’d followed a linear path — college to law school to law firm — and I’d long defined success through external markers like salary and prestige. That rigidity stifled other parts of myself. What would happen if I gave those parts room to grow?
Letting go of long-held notions, reinforced by a culture that prizes material wealth over all else, scared me.
A friend shared this advice: Go to what excites you, and you’ll be OK. That became my motto. I quit my job and headed out on the road.
By April 2016, I’d downsized from a one-bedroom apartment to a used station wagon and was pitching a tent along the Colorado River in Utah. It was the first night I camped alone, and I barely slept. In an arc over my head were “defense” tools: a flashlight, keys with a panic button, and another flashlight.
Way out of my comfort zone, I had no idea what I was doing, but I kept going, kept trusting I’d figure it out.
It turned out to be the best decision for me
Day by day, I did figure it out. Soon, I met others who were living out of their cars. Soon, I stopped arcing my head with defense tools. Soon, I slept better on dirt than anywhere else.
Over the following months, I opened myself in new ways. I made friends at trailheads and on trails, went backpacking or rock-climbing with those friends, and ran for miles in the wild without a watch or any goal other than exploration.
I made many mistakes. After a storm detoured me on a run, I spent the night in a stranger’s car. Through those mistakes, I learned to trust in the uncertainty.
When I drove west, I had no itinerary, but I held tight to one plan: In a spreadsheet, I’d mapped out how to climb every 14,000-foot peak in Colorado; there are almost 60. The goal quieted the lingering voice, telling me I was “wasting” time. If I climbed those mountains, just look how productive I would be. By late July, I’d abandoned the spreadsheet.
After a life of checking boxes, I started to find a different sort of success by chasing curiosity and going to what excites me. Eight years later, I no longer live in my car, I didn’t return to law, and I’m still chasing what excites me — and still building a life filled with 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.
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