About a year ago I started asking myself a question I couldn’t answer.
If this all works, then what?
At the time I was working in roofing sales and building my own roofing company on the side. Things were going well. I was making good money, learning fast, doing what looked like the obvious next step.
But every time I pictured the successful version of it, I hit the same wall. If the company worked, I’d grow it. Hire people. Take on more jobs. Make more money. Keep building for the next ten or twenty years.
For a lot of people, that’s the dream.
I couldn’t picture myself wanting it.
Not because I disliked roofing. Not because the business was failing. Not because there’s anything wrong with building a company. I just couldn’t find the version of that life, ten years out, that I actually wanted to be living.
Around the same time I was spending close to $4,000 a month to live what I considered a pretty normal life. Rent, utilities, groceries, insurance, gas. That’s a lot of money, and it wasn’t the problem. The problem was that I’d started wondering what all of it was for.
That question kept coming back. Not every day, but often enough that I stopped being able to ignore it.
Eventually I realized I wasn’t questioning my career. I was questioning the direction of my life.
This isn’t me trying to talk anyone into leaving the United States. It’s just how I got here.
It started with a layoff
I don’t think I’d be writing this if COVID had never happened.
Before 2020 I was an assistant manager at Panera Bread. It wasn’t a terrible job, but it wasn’t leading anywhere, and I wasn’t making it lead anywhere. I was existing.
Then COVID hit and I got laid off.
Instead of finding another job, I decided to finally finish college. I’d been putting it off for years and unemployment bought me enough room to do it full-time. I graduated in December 2020 with a business degree.
A few months later my lease was ending. College had been the only real reason I’d stayed close to home, and now it was done.
So I booked a one-way flight to Costa Rica.
There was no plan behind it. I wasn’t trying to become a digital nomad and I wasn’t leaving for good. I wanted to travel for a while before starting a career.
That trip lasted four months.
I thought I was going on vacation
Three of those months were in Costa Rica, which is the maximum an American can stay without a visa. Most of it I spent volunteering at a hostel I found through Workaway, a site that connects travelers with volunteer work in exchange for a bed and sometimes meals.
It wasn’t glamorous. I checked guests in, changed sheets, swept floors, and did whatever else came up, usually in the kind of heat that makes you plan your entire afternoon around finding shade.
When the three months ran out I still wasn’t ready to go home, so I crossed into Panama and volunteered at another hostel, this one on an island. That one was easier. I showed guests around, took people snorkeling off the dock, made sure everyone was having a good time. In exchange I got a bed and one meal a day.
None of it paid. I didn’t own much beyond what fit in my backpack.
But somewhere in those four months I noticed something. Life felt simple. A place to sleep, enough food, a new group of strangers every few days.
That was enough.
I didn’t appreciate it while it was happening. I was too busy living in it. It wasn’t until I got home that I understood those four months had quietly rearranged what I thought a good life looked like.
I just didn’t know it yet.
I came home to build a life
Not long after I landed, I opened a refillery.
The whole idea was to sell the things everybody buys wrapped in disposable plastic, without the disposable plastic. Five gallon buckets of shampoo, laundry detergent, dish soap, even deodorant. People brought in their own containers, or bought one from me, filled them up, and paid by weight. Alongside that I carried a big selection of plastic-free goods: reusable produce bags, reusable coffee filters, bamboo more or less everything.
It felt like exactly the right move. I’d always been interested in business, I’d just finished the degree, and I liked the idea of building something that was mine.
So I threw myself at it. Long days. Learning the register, the inventory, the rhythm of who walks in at what hour. Solving whatever broke that day. It was stressful and uncertain and I genuinely loved the challenge.
If you’d asked me then where my life was headed, I’d have told you I was going to spend the next several years growing that store. Travel had been great, but it had served its purpose. I’d had my adventure.
Everything fell apart
About six months in, I closed it.
Rising costs, inconsistent sales, and the reality that enthusiasm is not a business model. I learned more in those six months than I expected to. The numbers still didn’t work.
A few weeks later I filed for bankruptcy.
At the time it felt like total failure. I’d put everything I had into something I believed in, and I came out the other side with less money, more debt, and no idea what came next.
There’s an irony I didn’t catch until much later. My first business was built entirely on the premise that people buy more than they need. It took me another four years to apply that idea to my own life.
What I didn’t notice right away was that I’d also come out with almost no obligations. No lease. No employees. No business to run.
For the first time in years I could ask a different question.
If I’m starting over anyway, what would I actually do?
The answer surprised me. Instead of finding another apartment and another job, I put everything I owned into my car and drove west. I told myself it was temporary. Clear my head, make some money doing seasonal work, figure out the next move.
I moved into my car
For about a year I worked seasonal jobs across the western United States. California, Colorado, Arizona, New Mexico, Utah, Yellowstone. A few months in one place, then the next.
Most nights I slept in the car.
It wasn’t a minimalist statement, it was just what made sense. A lot of the jobs came with employee housing, but between seasons the car meant I could go anywhere without paying for a room I’d use for three weeks. Some mornings the dashboard would fog up before the engine warmed, and I’d get coffee from whatever gas station was open.
That stretch is when I started pulling apart the assumptions I’d been carrying around my whole adult life. Better apartment, more things, slowly build the life you’re supposed to build.
Instead I was living out of a Nissan Altima.
And I was happy. Not making-the-best-of-it happy. Actually happy.
My expenses were close to zero. Everything I owned fit in the trunk and the back seat. When I wasn’t working I was hiking, or wandering around some mountain town, or taking the long way to the next place.
Life was uncomplicated, and it gave me something I hadn’t had in years.
Time.
I wasn’t thinking about promotions or career paths. I was living one season at a time.
I don’t want to romanticize it. There were cold nights, hot nights, and plenty of days I’d have traded almost anything for a real bed and a hot shower. But I never felt like I was giving much up. If anything I started to notice how little of what I thought I needed was doing anything for me.
I left the country again
After that year I gave myself five more months abroad before starting a career for real.
If Costa Rica was the introduction, this was everything else.
I watched the sun come up over Angkor Wat. I spent days on a motorbike in the mountains of northern Vietnam, past rice terraces and switchbacks, with no particular idea where I’d sleep. I crossed from Europe into Asia by ferry in Istanbul and watched two continents blur into each other from the deck.
There were dozens of moments like that. A few were planned. Most weren’t.
And at the end of it I felt something I hadn’t felt after Costa Rica.
Satisfied.
There was no revelation waiting for me. The opposite, actually. I felt like I’d finally scratched the itch. I’d seen the places I’d been thinking about for years and proved to myself I could do it.
I flew home almost thirty years old, convinced I was finished.
That’s the funniest part of the whole story. I really believed it.
I tried the traditional path one more time
I did exactly what I’d planned. Found a career in roofing, rented an apartment, settled into a normal routine.
It went well. I worked my way up, earned promotions, and started making more money than I ever had. It was the first stretch of my adult life that felt like an actual career with a future attached to it. I liked the work, the people, and the fact that in sales your income is a direct readout of your effort.
Eventually I started planning the roofing company.
From the outside everything was pointing the right direction. I thought so too.
But every so often I’d catch myself back in those years. Not missing a vacation. Missing the feeling of possibility. Waking up somewhere I’d never been. Owning almost nothing. Knowing my life wasn’t tied to a single address.
I brushed it off for a long time. I’d done the travel thing. This was the chapter where I built something.
Then the question showed up and wouldn’t leave.
If I build the roofing company, then what?
Grow it. Hire people. More jobs, more money, ten or twenty more years.
The strange part wasn’t that it was a bad answer. It was realizing it wasn’t my answer anymore.
My definition of success changed
For a long time I thought this article was about leaving the United States.
I don’t think it is. I think it’s about how my definition of success changed, and how slowly it happened. Not one trip or one job or one decision. It moved so gradually I never caught it moving.
Every chapter handed me a different version of it. After college I thought success meant building a business. When that failed I thought I just needed a different business. After traveling I thought I’d gotten it out of my system. Then I found myself missing the life I’d supposedly finished.
None of those were wrong. They were accurate to whoever I was at the time.
The guy who opened a retail store wasn’t the same guy who spent a year in a car. The guy who flew to Costa Rica wasn’t the guy who came home from five months in Asia and Europe. And the guy who started planning a roofing company wasn’t the same one who kept asking “then what?”
Somewhere in there, success stopped looking like something I owned and started looking like the life I got to live on a normal Tuesday.
I still want to build a successful business. I still want financial security. Those didn’t go anywhere. They’re just not the destination now.
Today success looks like getting to decide where I wake up next month. It looks like experiences I’ll still have in twenty years instead of possessions I’ll replace in three. It looks like a business that supports my life instead of a life built around a business.
Maybe that definition changes again. I hope it does.
What it comes down to
The life I want was never going to require staying in one place.
I’m not leaving because I hate the United States. I’m not leaving because I think somewhere else is perfect. I’m not leaving because I think anyone else should.
I’m leaving because of a few things I’ve learned about myself. I need less than I was raised to think I need. I like building businesses, but I don’t want my whole life to orbit one. And I’m at my best when I can go somewhere I’ve never been and say yes to whatever happens there.
On February 21, 2027, I’m boarding another one-way flight.
This one feels different. I’m not going on vacation and I’m not running from anything.
I’m just building the life somewhere else.
Maybe I spend a few years abroad and come back. Maybe I end up living somewhere I haven’t visited yet. I don’t know.
And for the first time, that doesn’t bother me at all.
I’m documenting the whole thing, including the money. If you want to follow along, subscribe below.