After Her Dad's Death, Wisconsin Woman Sells Home to Hit the Road in a Truck

Life is short, so why not hit the gas? After losing her father unexpectedly, Ashley Kay, 36, from Wisconsin, decided to sell her house and travel full-time in a truck—proving that sometimes you need a little heartbreak to get moving.

Her father, Tom Kay, passed away in December 2015 at 57. In the wake of his passing, friends and family shared stories about Tom's adventurous spirit and globe-trotting ways. Inspired by his legacy, Ashley realized she wanted more out of life than her small town could offer.

She spent the next several years traveling around the world, but it was a chance encounter in Roatán, Honduras that truly set things in motion. While scuba diving, Ashley met a man who had quit his job in Austria and traveled the world without ever stepping on a plane—using hitchhiking, buses, and couch-surfing as his means of getting around. When she asked him what the worst part of his journey was, his answer was simple: he regretted not starting sooner. That was all the push Ashley needed.

In March 2023, she sold her three-bedroom family home and bought a $44,000 Toyota Tacoma as her new ride. With her loyal black lab, Porter, she set off for Baja, Mexico and has been exploring North and South America since, living the kind of road trip that most people only ever dream about.

Baja, Mexico quickly became her favorite stop—she says the place feels like home, with stunning nature, a beautiful ocean, and the pure joy of the Sea of Cortez. But the journey hasn’t all been sunsets and sand; Ashley’s had her share of truck troubles. She spent hours stranded in the remote Peruvian desert with suspension issues and even fixed a flat tire solo at 12,500 feet in Costa Rica. "Traveling solo like this is a ton of work," Ashley admits. "The day-to-day can really wear you down."

The hardest blow came in August 2024, when Porter, her loyal travel buddy, passed away. Now she’s on the road alone, facing uncertainty with the same determination that’s carried her this far. "Overall, all the issues get solved," Ashley says. "You just have to figure it out a little bit more and be patient." If patience is the price for freedom, she’s clearly paid in full.