In a story emblematic of a daring shift in lifestyle that many are beginning to embrace, Ashley Kaye’s journey from corporate life to full-time travel has gained traction as individuals seek more meaningful experiences in the wake of the pandemic. Kaye’s transition reflects both a personal evolution and broader societal questions about work-life balance, financial independence, and the quest for adventure.
Kaye inherited her childhood home in Waterford, Wisconsin, upon her father’s passing in 2015. Initially, the house symbolized stability and memory, yet as Kaye navigated her corporate healthcare career, she began to question whether her attachment to the property was a reflection of her desires or merely a societal expectation. “I started thinking, ‘Did I really want to live here forever?'” she said, revealing the internal conflict many face when transitioning from a stable lifestyle to one filled with uncertainty and potential.
Working in a high-pressure job that often required her to clock in 80 to 100 hours a week, Kaye found herself ensnared in a routine that blurred the lines between professional and personal life. “I was a zombie during those times,” she noted, reflecting on the isolation that accompanied remote work. This grueling schedule left her with little time to personally reflect, let alone explore other avenues of life.
A pivotal moment occurred during a scuba diving trip in Honduras, where Kaye encountered a fellow traveler who lived a nomadic lifestyle. Their conversations traversed the highs and lows of travel, including the financial aspects of living on the road. Influenced by this encounter, Kaye returned home inspired yet anxious, realizing she wanted to leave her corporate job to travel more extensively. By the time she officially resigned, she had approximately $37,000 in savings but faced the daunting challenge of adjusting to a life devoid of the structured work routine she had known.
The initial months post-resignation proved challenging. Kaye admitted, “I didn’t know how to just do nothing. The first few months were really hard.” However, once she found a rhythm in her travels, her confidence blossomed. “I’ve never looked back and don’t have a single regret about leaving,” Kaye stated, a sentiment that resonates with many exploring alternative lifestyles in an increasingly mobile world.
Kaye’s travels took on an unexpected direction during the COVID-19 pandemic. While in South Africa, she received news that her aunt was gravely ill, necessitating her return to Wisconsin. This experience solidified her desire for a more transient lifestyle. “I don’t want to be here. This isn’t it for me,” she recalls, marking a definitive shift in her mindset about home and belonging.
During her time caring for her aunt, Kaye prepared her childhood home for sale, considering future adventures. The decision to pursue van life emerged as she contemplated practicalities, like traveling with her dog. “Traveling by plane with a dog just sounded like a terrible idea,” Kaye reflected, showcasing the nuanced considerations that accompany a nomadic pursuit.
Kaye’s journey experienced a financial turning point when she received a cash offer of $320,000 for her home shortly after her aunt’s passing. This unexpected financial windfall provided a substantial boost to her travel plans, allowing her to explore options for a new mode of life. Kaye’s initial plan was thwarted when a coveted van, equipped for travel, sold before she could purchase it. However, seizing the moment, she purchased a Toyota Tacoma truck for $42,934, marking the beginning of a new chapter in her adventure.
In addition to her new vehicle, Kaye envisioned maintaining a permanent residence in the U.S., which led her to relocate to South Dakota—a state uniquely accommodating long-term residents without the need for physical presence. This strategic decision facilitated her travels while allowing her to keep one foot in the door of responsibilities back home.
After closing the sale of her Wisconsin house in March 2023, Kaye made the impulsive decision to drive to Baja California, Mexico, beginning an adventure filled with both spontaneity and contemplation. Living in a truck bed tent during this period, Kaye’s time in Baja led her to plan renovations for her truck to enhance its livability, reinforcing her dedication to combining travel with practicality.
Kaye’s renovations for her truck involved considerable financial investment, amounting to over $50,000. This expenditure included the purchase of a camper, the integration of solar power, and numerous enhancements aimed at improving functionality for life on the road. Throughout this process, she learned valuable lessons about logistics, resource management, and self-sufficiency—skills that are crucial for those embarking on similar journeys.
Despite the freedoms her lifestyle now affords her, Kaye remains acutely aware of the challenges and complexities of overlanding and navigating different countries. Some of these include legal hurdles, border crossings, and logistical maneuvers that can complicate even the most carefully laid plans. “There’s pros and cons to every mode of travel,” Kaye shared, identifying the delicate balance necessary for a life unconstrained by traditional boundaries.
With the truck fully prepared, Kaye resolved to traverse the Pan-American Highway, a journey renowned for its breathtaking scenery and diverse environments. Spanning from Alaska to Argentina, this route offers travelers the chance to dictate their pace and explore hidden gems along the way. As she articulated, “If you find somewhere that’s beautiful and peaceful, you can stay as long as you want.” This flexibility resonates with many who long for the ability to dictate their own circumstances, free from rigid schedules.
Kaye’s travels have taken her across more than 20 countries, including Mexico, several Central American nations, and parts of South America. While the lifestyle may appear idyllic, she cautioned against idealizing life on the road. “I don’t want to be a cliché and say it’s a dream life because it’s a lot of work.” Nevertheless, the freedom of choice that accompanies her lifestyle excites and inspires her daily life.
As Kaye has experienced personal growth through her travels, she credits her late father’s teachings—specifically, the belief that one can achieve anything—as a guiding principle. “His passing taught me how to live life,” she asserted, emphasizing the importance of seizing the moment, especially in light of life’s unpredictability.
Reflecting on her future, Kaye expresses little desire to return to a traditional life in the United States. The draw of community, affordability, and lifestyle options outside her home country showcase a shift in her identity and aspirations. “I like being able to live in towns where I can walk to get my groceries or walk to go to the doctor,” she articulated, identifying quality of life factors that define her ongoing journey.
Currently, Kaye is on a temporary hiatus from overlanding, having stored her truck in Argentina as winter approaches. She plans to spend the summer in Bermuda, a place she describes as a second home. Her affection for island life, characterized by friendly people and stunning natural beauty, reflects the culmination of her aspirations for a fulfilling lifestyle.
Kaye’s story is increasingly representative of a growing movement among individuals reevaluating their lives and making daring choices in pursuit of freedom and adventure. By selling her childhood home and investing in a life on the road, Kaye illustrates the complexities and rewards of personal transformation in contemporary society, signaling a potential awakening for those seeking a life less ordinary.