I’ve seriously considered living out of my car — not once, but multiple times. To some, that might sound like desperation. But for me, it’s about freedom.

This year alone, I’ve taken 17 trips to Chicago. I’ve been to Indy, Milwaukee, Ohio — always in motion. Somewhere along the way, I started questioning: What if “home” didn’t mean rent, leases, or a fixed address? What if it meant flexibility, autonomy, peace?

To be clear: living out of a vehicle isn’t always a last resort. For some, it’s a deliberate choice. A break from skyrocketing rents. A step off the treadmill. A path toward something simpler — and more meaningful.

No mortgage. No utility bills. Just a well-equipped car, a gym membership for showers, and remote work on the road. That’s not giving up. That’s redefining what it means to win.

And yet, people judge. They assume homelessness, failure, shame. But many folks in vans are financially stable, emotionally grounded, and radically intentional about their lives. They’re not running from something — they’re running to something.

Sure, there’s real hardship out there. We can’t ignore that. But there’s also a movement — people choosing less stuff, more freedom, and a new version of “success.”

So next time you see someone living on the road, maybe pause before you pity them. Because in a world chasing more, they might just have found enough. Sometimes, the road less traveled doesn’t lead to a dead end. Sometimes, it leads home.

It wasn’t always this way for me. The idea of living in a car had once seemed ridiculous. I remember a few years back, the thought of it being so far out of reach it felt like a distant fantasy, something people only did when they had no other choice. I had a job I hated, a small apartment I could barely afford, and a laundry list of things I thought I needed — things that weighed me down. My car wasn’t even a nice one. It was old, full of dents, with a broken air conditioner. But somehow, that car began to feel like it was my only escape.

I didn’t realize it at first, but the restlessness in me started building. It was a slow burn. Work got harder to stomach, and I found myself staying longer in places I hated, just to pay the rent. I’d come home after work, collapse on the couch, and waste hours in front of a screen. It was the same routine every day, and it felt suffocating. I started to wonder, “Is this all there is?”

I thought of my car. It wasn’t fancy, but it was always there. It was more than just a way to get from one place to another. It was a refuge, a temporary haven from everything I couldn’t control. It offered freedom in a world where I felt trapped. But I wasn’t ready to make the leap. I told myself it was silly — it was irresponsible. You don’t give up an apartment, a steady job, all for the sake of a car and a road trip. But that feeling of freedom stuck with me.

One weekend, I took a drive. Just to clear my head. I had no destination, no plan, just an open road. I drove through small towns, past vast fields and forests, and for the first time in what felt like forever, I felt alive. I parked by a lake, got out, and sat there for hours, watching the sun set. No deadlines. No pressures. No one telling me where I had to be or what I had to do. It was just me, the road, and the sky.

That was when I realized something. I didn’t need all the things I thought I did. My life didn’t have to be anchored to a single place. What I needed was freedom, the ability to pick up and go whenever I wanted. I didn’t need a high-paying job or a fancy apartment. I needed peace. I needed space.

The idea of living out of my car started to feel more like a possibility. I began researching it. I found online forums and blogs of people who had made this choice intentionally. They weren’t homeless. They weren’t running away from something. They were living life on their own terms. Some were traveling the country. Others had built out vans to live in full-time. And they all seemed so… content. It wasn’t easy, but it was simple. It was real.

At first, the idea of actually giving up my apartment and living on the road seemed crazy. But the more I thought about it, the more it started to make sense. I didn’t need a permanent address to be happy. I didn’t need the latest phone or a collection of stuff I never used. All I needed was a car, a few basics, and a purpose. I could work remotely, make enough to survive, and explore the world on my terms. It was like a lightbulb moment. I could live in a way that felt true to me.

So I did it. I let go of my apartment, sold what I didn’t need, and packed up my car. I found a cheap gym membership for showers and bathroom access, and I made sure I had a portable power bank for my electronics. I had a small cooler for food, and I kept things simple. My car became my home, my office, and my sanctuary. I was free.

At first, it was hard. I had doubts. I was constantly thinking I had made a mistake. What would people say? What if something went wrong? But I pushed through it. I stuck to my plan, and slowly, things began to fall into place. I started traveling more. I went to places I had always dreamed of but never had the time or money to visit. Chicago, Indy, Milwaukee — the cities and towns I had always heard of but never knew. Each place was an adventure. Each road I traveled led me closer to myself.

I found joy in the small things: cooking meals in parking lots, finding new spots to park for the night, waking up to the sound of birds chirping. There was a quiet satisfaction in simplicity. I didn’t need a fancy breakfast or a soft mattress. I just needed a space to be myself, and I was finding that, more and more, on the road.

But, of course, it wasn’t all easy. There were challenges. There were days when I ran out of money, or when the weather was too cold or too hot. I struggled to find reliable places to park at times. People stared. Some asked questions. Some even offered help, assuming I was homeless. But instead of feeling ashamed, I felt empowered. I was living my truth. I had chosen this path.

One of the biggest surprises came from the connections I made. I had always thought of myself as someone who kept to myself. But when you live on the road, you meet people you wouldn’t expect. Fellow travelers. Locals. People from all walks of life. There was an unspoken understanding between us. We weren’t just passing through — we were living. And in that shared experience, I found a sense of community that I had never anticipated.

I remember one night, parked on a quiet street in a small town, a woman knocked on my window. I was half asleep, but when I rolled it down, she offered me a bag of homemade cookies and a smile. “I saw you parked here earlier,” she said. “You seem like you could use a little comfort.” I was taken aback. It wasn’t much, but it was kindness. In that moment, I realized something important — this lifestyle, this choice, wasn’t about being alone. It was about finding connection, in unexpected ways.

But there were also moments of doubt. Moments when the weight of it all hit me. It was easy to romanticize the idea of living on the road, but there were times when I missed the comfort of a stable home. I missed having a bed that didn’t double as a couch and a place where I could just lay my head without worrying about the next stop. And I missed being around people who understood. Sometimes, the loneliness crept in, and I found myself questioning if I had made the right decision.

It was during one of these moments that I met Jonah. He was in his mid-thirties, and like me, he had decided to leave behind a traditional life for something more… fluid. We met at a small park in Cleveland, sitting on the grass, sharing stories about the road. Jonah had been living in his van for almost a year, and he told me about his travels, the highs and lows, the lessons he had learned. He said something that stuck with me: “The road doesn’t always make sense. It’s not easy. But it shows you who you really are.”

Jonah’s words were like a wake-up call. I realized I wasn’t just running away from something; I was running toward something. I was discovering pieces of myself I had never known existed. I was learning to be comfortable with uncertainty, with impermanence. I was no longer just surviving; I was living. It wasn’t always easy, but it was always real.

A few months after meeting Jonah, I found myself in a small town in Michigan, where I got an unexpected job offer. It wasn’t much, but it was enough. It was a remote gig that allowed me to continue living on the road, but with a more consistent income. It felt like everything had aligned, and for the first time in a long time, I felt like I was on the right path.

Living in my car wasn’t just about escaping the system; it was about embracing a new kind of life. It wasn’t perfect, but it was mine. And every day, I got a little bit closer to understanding what it meant to live freely, truly, and without apology.

Sometimes, the road less traveled doesn’t lead to a dead end. Sometimes, it leads to a place of peace, of purpose, and of discovery. And maybe that’s the greatest reward of all — finding your way home, wherever that may be.

If you’ve ever considered something different, something outside the box, something that might not make sense to others, don’t be afraid to take the leap. You might just find that the path you least expect is the one that leads you to exactly where you need to be. Share this if you’ve ever felt like taking a chance, or if you’ve taken that road yourself. Life’s too short to wait for someone else to define what success looks like. Go find your own version.