In 2015, Ashley Kaye’s life took an unexpected turn. Her father passed away, leaving her the house she grew up in, located in Waterford, Wisconsin. At just 27, Kaye was working in corporate healthcare, transitioning into a demanding consulting job that had her clocking 80 to 100 hours a week.
“I was basically a zombie,” says Kaye, now 36. “I worked from home, just walking from the bedroom to the office to the kitchen and back again.”
Everything changed after a scuba diving trip to Honduras. There, Kaye met a fellow traveler who opened her eyes to a different way of living.
“He said he wished he’d started traveling sooner because it was easier and cheaper than he thought,” she recalls. “That flipped a switch for me. I went home, worked even harder, and eventually quit the next year.”
From Career Climber to World Explorer
Over the next three years, Kaye traveled extensively—even during the COVID-19 pandemic. But a sudden family emergency brought her back to Wisconsin. While in South Africa, she learned her aunt was sick and needed care. She boarded a flight home—but her heart wasn’t in it.
“On that flight, every part of me felt, ‘I don’t want to go back. This isn’t my life anymore,’” she says. “I belong near the ocean. That’s when I stopped hesitating—I was ready to sell the house.”
While preparing the house for sale, Kaye began researching ways to keep traveling, this time with her dog. Flying didn’t feel like the right option. She was drawn to the idea of overlanding—self-reliant travel in a vehicle—and considered building a mobile home on wheels.
Around that time, she connected with a couple on Instagram who had explored South Africa in a Toyota truck with a camper. Inspired, Kaye dove into research and soon purchased her own Toyota Tacoma for $42,934.
A New Home on Four Wheels
After picking up the truck in South Dakota, she drove it back to Wisconsin and finalized the sale of her childhood home in March 2023. With that chapter closed, she began planning her new life.
Her first stop: Baja California, Mexico, where she spent three months mapping out the upgrades she needed to make the truck livable. “Most people plan for years before starting something like this. I didn’t even have a truck when I accepted the offer on my house,” she laughs. “I just knew I had to figure it out as I went.”
While waiting for key parts—like a new truck bed with external storage—Kaye threw herself into learning about truck life. So far, she’s invested over $50,000 in renovations, including:
- A camper installation
- Solar power setup
- New suspension and tires
- A custom bumper
- An electric cooler
- A complete truck bed replacement
She also repurposed items from her family home, bringing a piece of her past into her future.
Life on the Pan-American Highway
Once her truck was ready, Kaye set off to drive the Pan-American Highway—an epic route from Alaska to Argentina. She began her journey in Denver and never looked back.
“It’s an incredible way to travel. You move at your own pace. If you find a beautiful, peaceful place, you stay,” she says. “But it’s not all sunsets and selfies—crossing borders solo can be exhausting. Still, it’s one of the coolest things I’ve ever done.”
So far, Kaye has visited over 20 countries, including Mexico, all of Central America, Colombia, Ecuador, Peru, Chile, and parts of Argentina.
The Biggest Lesson: Start Living Now
Though the lifestyle requires constant upkeep and problem-solving, Kaye says it’s been worth it.
“It’s not some fantasy. It’s hard work,” she explains. “But it’s amazing to wake up, look at a map, and ask, ‘Should I sleep in a volcano, the jungle, or by the beach tonight?’ Those choices are incredible.”
Looking back, she says her biggest lesson is simple: life is short—start now.
“You don’t have to quit your job and travel the world like I did. But whatever your dream is, don’t wait,” she urges. “Just start.”
Her late father’s words stay with her. “He used to tell me every day, ‘You can be anything you want and do anything.’ He died at 57—he never even got to retire. Losing him taught me that we can’t wait forever to live.”
