After her father passed away in 2015, Ashley Kaye inherited her childhood home in Waterford, Wisconsin. The three-bedroom house held sentimental value, but Kaye, then 36, began to question if staying there aligned with her growing desire to explore the world. Her demanding career in corporate healthcare and later consulting, with 80 to 100-hour workweeks, left her feeling burnt out and disconnected from a fulfilling lifestyle.
While on a scuba diving trip in Honduras, Kaye met a full-time traveler who changed her perspective. Their deep conversations about freedom, finances, and regret made her realize that long-term travel was more accessible than she had believed. Motivated, she returned home with a renewed sense of purpose, saved aggressively, and eventually quit her job with $37,000 in savings—despite early doubts and identity struggles around no longer having traditional work.
From Pandemic Realization to Truck Life: Selling Home and Embracing Nomadic Overlanding Adventure
Kaye spent the next three years traveling through the pandemic, and it was during a trip to South Africa that she had an emotional realization: returning home no longer felt right. When she flew back to Wisconsin to care for her ailing aunt, it became clear that her true happiness was tied to being near the ocean and living a nomadic lifestyle. That clarity gave her the confidence to sell her home and fully embrace travel.
As she prepared to sell her house, Kaye considered van life with her dog. Her needs—access to remote locations for photography and ease of travel with a pet—led her to look into overlanding. She missed out on one ideal van, but almost immediately received a cash offer of $320,000 for her house. Around the same time, a couple she met on Instagram introduced her to the concept of truck-based overlanding, which quickly became her next adventure.
Selling Her House and Hitting the Road Helped One Woman Reclaim Her LifeKaye bought a Toyota Tacoma truck for $42,934 and established permanent U.S. residency in South Dakota, which required no physical presence. She then returned to Wisconsin to finalize her home sale in March 2023 and began traveling. Starting with a basic truck bed tent in Baja California, she slowly upgraded her setup. Renovations included solar panels, a camper, new suspension, tires, and more, totaling over $50,000.
Embracing Freedom and Challenges on a Life-Changing Overland Journey Across the Americas
With her truck fully outfitted, Kaye committed to overlanding the Pan-American Highway, stretching from Alaska to Argentina. While the journey offered unmatched freedom and breathtaking locations, she noted the challenges of solo travel, including border logistics and vehicle upkeep. Despite the difficulties, she described the adventure as one of the most rewarding experiences of her life.
So far, Kaye has traveled through every Central American country, much of South America, and over 20 countries in total. She emphasized that although her lifestyle isn’t always easy, the freedom to choose where to go—whether a beach, volcano, or jungle—is deeply fulfilling. She typically stays in each country for the full duration of her visa, usually around 90 days, and has developed a deep sense of resilience and capability.
Kaye says she no longer feels drawn to live in the U.S., citing affordability, walkability, and quality of life abroad as key reasons. She is currently on a break from overlanding, with her truck stored in Argentina, and plans to spend the summer in Bermuda—a place she considers home. Kaye reflects that her father’s early passing shaped her desire to truly live life, a philosophy that continues to drive her unconventional but meaningful journey.
