Breaking Free: How Overlanding Liberated Me from the 9-to-5 Grind

Dispersed camping at Alstrom’s Point, north of Lake Powell, Utah.

Breaking Free: How Overlanding Liberated Me from the 9-to-5 Grind

By David Wade

The alarm blared at 6:00 a.m., a sound that once felt like a death knell for my soul. For decades, I dragged myself out of bed, shuffled through the morning routine, and joined the bleary-eyed masses on the commute to a cubicle that seemed to shrink with every passing day. The fluorescent lights, the endless meetings, the inbox that never emptied—it was a life of predictable monotony, a slow drip of dissatisfaction that I begrudgingly accepted as “normal.” But then, something horrible happened, I was laid off and the chaos that followed put me into a completely different lifestyle that changed everything.  My wife and I became overlanders. The open road, a rugged vehicle, and a life untethered from the 9-to-5 became my salvation. This is the story of how overlanding didn’t just free me from a desk job—it gave me a new way to live.

The Cubicle Cage

I wasn’t always miserable. When I landed my first “real” job after the military, I felt a surge of pride. A steady paycheck, benefits, a title—it was the American Dream, or so I thought. I worked in mortgage banking, crafting financing solutions for people I didn’t know, sitting through brainstorming sessions that felt more like exercises in futility. The days blended into weeks, then years.

I was good at my job, very good, but it didn’t matter. The promotions came, but so did the realization that I was trading my time—my life—for a paycheck that barely covered the cost of existing.

My wife and I started a Jeep club in Central Florida when COVID hit.  It was a great way enjoy life during a world-wide pandemic.  Through that group, which we affectionately named the Dirty Bunch Jeep Club, we began traveling all of the Florida to ride trails.  Soon, Florida was not enough and we were going out of state.  Weekend trips soon grew to 10-day overlanding adventures as we explored new areas together.  When I was laid off, we began to create a business that would allow us to earn what we needed while living out of our Jeep for extended periods of time. 

What Is Overlanding?

For the uninitiated, overlanding is more than just off-roading or camping. It’s a self-reliant journey, often spanning weeks or months, where your vehicle is your home, and the world is your destination. Think of it as backpacking with a 4x4, equipped to handle remote terrains and unpredictable conditions. Overlanders carry everything they need—food, water, shelter, tools—and embrace the challenge of navigating the unknown. It’s not about the destination; it’s about the journey, the self-discovery, and the freedom to go where the pavement ends.

We started small, researching rigs and gear, binge-watching YouTube channels, and joining online forums. The community was welcoming, a mix of grizzled veterans and wide-eyed newbies.  We met dozens of others who were looking to do the exact same thing we were; escape the insanity of the daily grind. 

Horseshoe Bend, near Page, Arizona.

The Leap

Losing my job wasn’t easy. We had savings, but not a fortune. We had doubts, but also a burning desire to break free.  We planned an extraordinary journey as a real test for us; something that would tell us whether or not we were cut out for this.  With some planning and a tremendous amount of courage, we left our home behind and spent the next few months chasing this dream.

We drove from Orlando, Florida to the Outer Banks of South Carolina.  From Nags Head, we launched onto a 7 week, 7,000-mile cross country, coast to coast adventure of a lifetime on the Transamerica Trail.  It tested us in ways we did not expect and showed us parts of ourselves we did not know.  At first, we questioned whether or not we were doing the right thing.  Our family and friends thought we had lost our minds … some still do.  Others cheered us on and encouraged us to continue. 

We saw amazing things and explored areas we didn’t even know existed.  As we approached the Oregon coast, we expected that we would feel a sense of accomplishment and a hard line that indicated that we had done what we set out to do.  Oddly enough, reaching our goal didn’t feel like the end.  Neither of us could explain it at the time but somehow, we just didn’t feel like we were done.  Looking back on it now, I suppose that was the answer to our question as to whether or not we were ready for this. 

A New Kind of Work

Overlanding didn’t just free me from the 9-to-5; it redefined what work could be. We weren’t wealthy, so we had to find ways to sustain our lifestyle. I started narrating books for Audible, sharing my adventures on YouTube, created gear reviews, and tips for new overlanders. To my surprise, it gained traction. Brands reached out, offering sponsorships of gear in exchange for reviews. We learned photography and videography, turning our journeys into content for media. What began as a passion project became a viable income stream—not enough to get rich, but enough to keep the tank full and the pantry stocked.

I also picked up freelance work, writing for outdoor magazines and consulting for small adventure brands. The beauty of this work was its flexibility. I could write from a campsite in Colorado or edit videos from a coffee shop in Montana. My office was wherever I parked my rig. The hustle was real, but it was my hustle, on my terms. I wasn’t punching a clock; I was building a life that aligned with my values.

The Challenges of Freedom

Overlanding isn’t all Instagram-worthy sunsets and carefree vibes. It’s hard work, and it comes with its own set of challenges. Mechanical breakdowns are a fact of life—our rear axle gave out in the middle of Kansas, leaving us stranded for days. Weather can turn brutal; we’ve weathered thunderstorms that shook our tent and snowstorms that buried our rig.

Money is another constant concern. Income is irregular, and unexpected expenses—like a new set of tires or a cracked windshield—can throw the budget into chaos. We’ve learned to be frugal, to prioritize experiences over material things. A $10 campsite with a million-dollar view beats a $200 hotel room any day.

Then there’s the societal pressure. Friends back home, tethered to their mortgages and careers, sometimes look at me with a mix of envy and pity. “When are you going to settle down?” they ask. I used to feel defensive, but now I just smile. Settling down doesn’t mean a house and a desk job; it means finding peace in the life you’ve chosen. For me, right now, that’s the road.

The Rewards of the Road

The challenges are real, but the rewards are indescribable. Overlanding has given me a front-row seat to the world’s beauty. I’ve watched the Milky Way stretch across the sky in Teton National Park, listened to coyotes howl in the Arkansas forest, and felt the spray of waterfalls in the Bryce Canyon. I’ve met people who’ve changed my perspective—fellow overlanders, small-town locals, even camp neighbors who have shared stories around a campfire.

This lifestyle has also taught me resilience. Every breakdown, every wrong turn, every night spent shivering in a poorly pitched tent has made me stronger. I’ve learned to trust my instincts, to problem-solve under pressure, and to find joy in the unexpected. Overlanding isn’t just about travel; it’s about growth.

Perhaps the greatest reward is freedom. Not just the freedom to go where we want, but the freedom to be who we want. I’m no longer defined by a job title or a paycheck. I’m a storyteller, an explorer, a student of the world … a student of life. My days are mine to shape, whether I’m chasing a sunset or spending a quiet morning with a book and a cup of coffee. This is what it means to live on your own terms.

A Call to the Curious

If you’re reading this, stuck in a job that drains you, dreaming of something more, let me offer a gentle nudge: you don’t have to stay chained to the 9-to-5. Overlanding isn’t the only path to freedom, but it’s one that’s worked for me. Start small—a weekend trip, a used 4x4, a single step toward the life you want. The road is out there, waiting. All you have to do is take it.