Waterford, Wisconsin – In 2015, Ashley Kaye faced a profound turning point when she inherited her childhood home following her father’s death. At just 27, she was deeply entrenched in a demanding corporate healthcare career, often logging up to 100 hours a week. As she reflected on that time nearly a decade later, Kaye described herself as feeling like a “zombie,” endlessly shuttling between her home office and kitchen.
A pivotal experience came during a scuba diving trip to Honduras, where Kaye met someone who inspired her to re-evaluate her life choices. Their conversations about traveling and financial freedom ignited an urge within her to break away from the corporate grind. Shortly thereafter, she resigned from her job and embraced a life on the road.
Kaye’s adventures took her to over 20 countries but were temporarily paused during the COVID-19 pandemic. While visiting South Africa, she received the news that her aunt was gravely ill. The return flight to Wisconsin forced her to confront her feelings about leaving the life she had built for herself as a nomad. It became clear to her that the allure of travel and oceanfront living greatly outweighed the comforts of home.
In the midst of caring for her aunt, Kaye began preparing her childhood residence for sale, which marked a major step toward her future plans. She envisioned a life on the road with her dog, considering alternatives to traditional air travel that could hinder their adventures together. It was during this transition that she discovered the world of overlanding—self-reliant travel to remote destinations—after connecting with fellow travelers on Instagram.
After selling her home, Kaye invested in a Toyota Tacoma truck, modifying it to serve as both living space and transport. She estimated her renovations would exceed $50,000, incorporating features such as solar power and upgraded suspension. These changes would allow her to better navigate tougher terrains, facilitating her photography and travel ambitions.
With her truck ready, Kaye embarked on her first major journey to Baja California, spending three months fine-tuning her living arrangements. Embracing spontaneity, she intentionally avoided meticulous planning, opting instead for a more flexible approach that characterized her travels.
Since then, Kaye has driven along the expansive Pan-American Highway, which stretches from Alaska to Argentina. This route has affirmed her beliefs about the joys of setting her own pace and finding beauty in unexpected places, though she acknowledges the challenges that come with border crossings and logistical hurdles.
Reflecting on her travels, Kaye notes, “Life is too short, so just live.” The journey has allowed her to visit numerous countries, constructing experiences that extend far beyond mere sightseeing. She emphasizes that while traveling is rewarding, it demands commitment and effort, opposing the notion of an idyllic, carefree lifestyle often portrayed in media.
Kaye attributes her adventurous spirit to the teachings of her late father, who encouraged her that anything was possible. His passing, along with the lessons learned during her travels, drives her to pursue her dreams vigorously and to advocate for others to do the same—whether that means quitting their jobs to explore the world or achieving personal goals in their own way.
Through her journey, she hopes to inspire others to cherish their time and make the most of their lives, a lesson echoed in her father’s words.