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Ashley Kaye inherited her childhood home in Waterford, Wisconsin, following the death of her father in 2015. While she initially grappled with the idea of whether she wanted to live there indefinitely, her love for travel and exploration ultimately dictated her next steps. "I loved my home because of the many memories, but my yearning to travel was stronger," shared Kaye, 36, in an interview with CNBC Make It.

Kaye was initially ensconced in a demanding career in corporate healthcare before transitioning into consulting, which saw her working up to 100 hours a week. She described this phase of her life as a monotonous routine that drained her energy and left her feeling like a "zombie." Everything changed during a scuba diving trip in Honduras, where she met an avid traveler who inspired her to rethink her life’s trajectory.

Motivated by their conversation, Kaye returned home with a renewed resolve. A year later, she quit her job with $37,000 in savings but found it difficult to adjust initially. Doubts plagued her during those early months. However, once she settled into her travel rhythm, Kaye's confidence grew, and she never looked back.

Her wanderlust saw her through three years of continuous travel even as the pandemic raged on. An unexpected call about her aunt's illness brought her back to Wisconsin. It was during this return that Kaye realized she no longer felt at home in Wisconsin and decided to sell the house.

With the house selling for $320,000 in March 2023, Kaye began exploring the possibility of van life. A perfect van eluded her initially, but a chance encounter on Instagram introduced her to overlanding – a form of self-reliant travel often involving off-road vehicles. Inspired, Kaye invested $42,934 in a Toyota Tacoma truck, customized to facilitate her travels.

Kaye created a new permanent residence in South Dakota, which allowed her to maintain a U.S. address without the need for physical presence. Following the sale of her house, she drove to Baja California in Mexico and started planning renovations for her truck to make it more livable for her and her dog.

The truck underwent extensive modifications, including a camper purchase, solar power installation, and suspension upgrades, amounting to over $50,000. Upon completion, Kaye embarked on her most ambitious journey yet: traveling the Pan-American Highway from Colorado to the southern tip of Argentina.

Since then, her travels have taken her through Mexico, several Central American countries, and across South America, including Colombia, Ecuador, Peru, Chile, and Argentina. Each new destination offers fresh experiences and challenges. "It's a lot of work, but the freedom to choose my surroundings is priceless," Kaye said.

She stays in each country for the full duration of her visa, typically around 90 days. "I've learned that I'm capable of anything," Kaye remarked, reflecting on the lessons her travels have taught her. The memory of her father's encouragement serves as a constant source of motivation.

Currently, Kaye is taking a break from overlanding, with her truck stored in Argentina. She plans to spend the summer in Bermuda, a place she feels deeply connected to since her first visit at age 25. "Bermuda feels like home; it’s where I can dive into a friendly community and natural beauty at the same time," Kaye said.

With no plans to return to the U.S., Kaye has embraced a life of endless possibilities and scenic landscapes, finding solace and excitement in her ever-changing environment.