How Overlanding Builds Confidence: Embracing Adventures and Living Your Best Life
How Overlanding Builds Confidence: Embracing Adventures and Living Your Best Life
By David Wade, May 22, 2025
The sun was beating down on the dusty desert road west of Sedona, Arizona, as we rolled through brush and scrub. It was a glorious day, the brilliant blue sky providing the perfect backdrop to the deep reds of the rock formations rising all around us. The trail was rough—very rough—forcing us to drive slowly, but that allowed us more time to soak in the stunning imagery, so we didn’t mind. As we rounded a corner, we stopped to size up a new challenge: a severely steep incline rising 50 feet before us. Its surface was an undulating mix of rocks and dirt, creating steps anywhere from 6 to 24 inches tall, interspersed with shelves and loose dirt. For the uninitiated, this would have been daunting. For my wife, Tiffany, it was just another day at the office. Without a word, she shifted the truck into 4-low, turned on the lockers, and slowly crawled our rig to the top.
Five years ago, Tiffany would have had serious concerns about making that climb. Doubt would have tried to prevent her from even attempting it. But today, after years of overlanding across North America’s wild landscapes, she had no hesitations. Countless obstacles, many far more challenging than this one, had been faced and conquered by her in our rig. Having tackled those and emerged victorious, this morning’s challenge seemed like nothing to her. We call that confidence, and it’s the byproduct of positive, successful experiences.
The Call of Overlanding
Overlanding is more than just off-road driving or camping in remote places. It’s a lifestyle that combines self-reliance, exploration, and a deep connection with the natural world. Across North America, from the rugged deserts of the Southwest to the dense forests of the Pacific Northwest and the windswept plains of the Midwest, overlanding offers a unique way to experience the continent’s diverse landscapes. But beyond the breathtaking vistas and adrenaline-pumping trails, overlanding fosters personal growth, particularly in building confidence. It’s a journey that challenges you physically, mentally, and emotionally, teaching you to trust yourself in ways you never thought possible.
For those unfamiliar, overlanding involves self-sufficient travel over long distances, often through remote and rugged terrain, with the goal of exploration and adventure. Unlike traditional camping or road trips, overlanding emphasizes living on the move, carrying everything you need in a capable vehicle—whether it’s a modified Jeep, a Toyota Tacoma, or a fully kitted-out overland rig. It’s about embracing the unknown, solving problems on the fly, and finding joy in the journey itself.
Tiffany enjoying the view in Grand Teton National Park.
Confidence Through Challenge
Tiffany’s story is a testament to how overlanding transforms doubt into determination. When we first started, she was hesitant behind the wheel of our Jeep Wrangler. The idea of navigating boulder-strewn trails or crossing rivers felt overwhelming. But overlanding isn’t just about driving skills—it’s about facing fears, learning from mistakes, and building resilience. Each trail, each obstacle, each night spent under the stars adds a layer of confidence that carries over into everyday life.
Our first major trip was an 11 day adventure with our Jeep club hitting the Badge of Honor trails of the East Coast. Tiffany was nervous, but she took the wheel. With guidance, she navigated slickrock climbs and sandy washes. By the end of that trip, she was no longer the timid driver who’d started. She’d learned to read terrain, trust the vehicle, and, most importantly, trust herself.
This is the essence of overlanding: it forces you to confront challenges head-on. Whether it’s a steep incline in Arizona, a muddy track in Oregon’s Tillamook State Forest, or a rocky pass in Colorado’s San Juan Mountains, each obstacle teaches you something new. You learn to assess risks, make decisions under pressure, and adapt when things don’t go as planned. Over time, these experiences build a quiet confidence that permeates every aspect of your life.
Self-Reliance and Problem-Solving
Overlanding is as much about mental fortitude as it is about physical skill. When you’re miles from civilization, there’s no roadside assistance or quick fix. You have to rely on yourself and your gear. This self-reliance is a cornerstone of the confidence overlanding builds.
Take, for example, a trip we took through Alabama’s Stoney Lonesome Offroad Park. Halfway through a remote trail, we heard a loud hiss—a punctured tire. For many, this would be a trip-ender. But overlanding teaches you to be prepared. We had a spare tire, a jack, and the tools to fix it. Within an hour, we were back on the trail, the setback forgotten.
These moments—fixing a tire, winching a stuck vehicle, or navigating a wrong turn—build a sense of capability. You learn to trust your preparation and problem-solving skills. Over time, this translates into a broader confidence in your ability to tackle challenges, whether on the trail or in daily life.
Living Your Best Life
At its core, overlanding is about living your best life. It’s about breaking free from routine, embracing adventure, and discovering what you’re capable of. The confidence gained on the trail doesn’t stay there—it transforms how you approach challenges at work, in relationships, and in personal growth.
For Tiffany, overlanding has been a journey of self-discovery. She’s gone from someone who doubted her ability to drive off-road to someone who tackles obstacles with ease. That confidence has spilled over into other areas of her life. In difficult situations, she’s more at peace and less likely to knee jerk reactions.
Our travels have taken us to some of North America’s most iconic destinations: the red rock canyons of Zion National Park, the alpine meadows of Logan, the windswept dunes of Great Sand Dunes National Park. Each trip has added to our confidence, not just as overlanders but as individuals. We’ve learned to trust ourselves, to work as a team, and to find joy in the unexpected.
Getting Started
If you’re inspired to try overlanding, the good news is that you don’t need a fully built rig or years of experience to start. Begin with a capable vehicle—something with four-wheel drive and decent ground clearance. A used Jeep Cherokee or Toyota 4Runner can be a great entry point. Equip it with the essentials: all-terrain tires, a recovery kit, and camping gear. Start with easy trails, like those in Pisgah National Forest in North Carolina or Ocala National Forest in Florida, and work your way up.
Join online forums or local overlanding groups to learn from others. Many camping and Overlanding events offer workshops and networking opportunities. Most importantly, embrace the learning process. Every mistake is a chance to grow, and every success builds your confidence.
The Road Ahead
As we crested the incline in Sedona, Tiffany turned to me with a grin. “That was fun,” she said, her voice brimming with the quiet confidence of someone who knows they can handle whatever comes next. That’s the gift of overlanding. It’s not just about the places you go—it’s about who you become along the way.
Whether you’re navigating a rocky trail in Colorado, camping under the stars in Montana, or crossing the border into Canada’s wild north, overlanding is a journey of self-discovery. It teaches you to trust yourself, embrace challenges, and live life to the fullest. So, pack your rig, hit the trail, and discover the confidence that comes from exploring North America’s vast, beautiful wilderness.