36-year-old sold her childhood home in Wisconsin to live and travel in a truck she spent $50,000 renovating: 'I don't have a single regret'

CNBC

12 hours ago

Ashley Kaye's father passed away in 2015 and she inherited her childhood home — a three-bedroom, one-bathroom house in Waterford, Wisconsin.
"I started thinking, 'Did I really want to live here forever?' Of course, because I didn't really want to let go of that huge chapter of my life," Kaye, 36, tells CNBC Make It. "But I had already been traveling a bit and knew that I wanted to keep traveling more and more."
At the time, Kaye was working in corporate healthcare and then transitioned to a consulting job, where she worked 80 to 100 hours a week.
"I worked from home so I just walked from my bedroom to my office to the kitchen and repeat," Kaye says. "I was a zombie in those times,"
While on a scuba diving trip in Honduras, Kaye met someone who travels full-time and realized she wanted to leave her career behind and keep traveling, too.
"We just hit it off and chatted the whole time I was there. We spoke about the worst of the worst, the best of the best, and financials, too," Kaye says.
"He told me he wished he had done it sooner because it's so much easier and cheaper than you think. That changed everything for me. I went home and worked more and more until I quit the next year."
When Kaye quit her job, she says she had about $37,000 in savings. But she struggled with not having a job to fill the time anymore.
"I didn't know how to just do nothing. The first few months were really hard and I wasn't sure if I was making the right decision," she says.
"Once I got into my rhythm of traveling and growing my confidence through that experience, I've never looked back and don't have a single regret about leaving."
Kaye spent the next three years traveling during the covid-19 pandemic. While on a trip to South Africa, she received unexpected news that her aunt was ill and she'd need to fly back home to Wisconsin.
"That flight was probably the moment where not a single ounce of my being was like 'Yay, I'm going home.' It was like, 'I don't want to be here. This isn't it for me.'," she says. "I love being on the islands. I love having the ocean near me. That took away the hesitation I had in previous years about selling the house."
While Kaye was back home caring for her aunt, she prepared the house for sale and considered her next move. She thought a lot about trying van life and living and traveling with her dog.
"Traveling by plane with a dog just sounded like a terrible idea," she says. "I do a lot of photography, so I knew I wanted something where I could reach tougher destinations."
Kaye found the perfect van — it had four-wheel drive and had been recently renovated and upgraded. But it sold before she was able to buy it. The very next day, she got a cash offer on her house for $320,000.
While waiting for the sale of her home to close, a couple reached out to Kaye on Instagram to ask about her time in South Africa. They shared their experience overlanding in a Toyota truck with a camper in the truck bed.
Overlanding is a form of self-reliant travel that involves adventuring to remote destinations, typically in a vehicle of some type.
After doing a bit of her own research, Kaye was all-in and purchased a Toyota Tacoma truck for $42,934, according to documents reviewed by CNBC Make It.
Even while traveling, Kaye still wanted to maintain a permanent residence in the U.S.. She decided to move to South Dakota — a state that allows for permanent residence without requiring a physical presence.
That same week Kaye bought the truck, she flew to South Dakota and had her new home delivered there.
She then drove the truck back to Wisconsin to finish packing up. The house officially sold in March 2023.
"I was like 'Ok, cool. We'll figure out all of the rest of the pieces later.' I closed on my house about three weeks after that, got the truck and drove to Baja [California], Mexico," she says.
On her drive down, Kaye lived in a tent that was specifically made to fit in the truck bed.
Kaye stayed in Baja California for three months and planned out the renovations she would need to make the truck more livable.
"My life is kind of like 'the plan is there is no plan.' Most people plan this type of adventure for years. I didn't even have a truck when I accepted the offer on my house," she says.
"It was very spur of the moment, so I needed to take a pause and figure things out."
In Mexico, Kaye found an American company that made truck bed replacements that would provide external storage and make it easier for her to live and travel in the truck, but the installation couldn't happen until September.
In the meantime, Kaye learned as much as she could about the truck and the kind of camper she would need. She estimates that she has spent over $50,000 on the renovations.
Costs included purchasing a camper, adding solar power, replacing the truck bed, upgrading the suspension, new tires, customizing a bumper, and installing an electric cooler.
When the truck was ready, Kaye decided to journey the Pan-American Highway, starting in Denver. The highway stretches from Prudhoe Bay, Alaska to Ushuaia, Argentina.
"It's really an incredible way to travel because you get to set your own pace and if you find somewhere that's beautiful and peaceful you can stay as long as you want," Kaye says.
"But there's pros and cons to every mode of travel and a lot of red tape and logistics crossing borders. It can be exhausting, especially when you're alone. You have to find a balance that works for you, but overall, it's definitely one of the coolest adventures of my lifetime."
Since living and traveling in the truck full-time, Kaye has visited Mexico, every country in Central America, Colombia, Ecuador, Peru, Chile and parts of Argentina. In total, she's been to over 20 countries so far.
"I don't want to be a cliché and say it's a dream life because it's a lot of work and there are a lot of things that you need to take care of and maintain," she says.
"But it's really incredible to be able to wake up and just look at the map and say, 'Should I go sleep inside this volcano or go to the jungle or go to the beach?' You have a lot of really beautiful options, so I can't really complain."
Kaye stays for the entirety of her visa in each country she visits, which is usually around 90 days.
She's learned one key thing about herself, Kaye says: She is capable of anything.
"I grew up with my dad raising me and telling me every day 'You can be anything you want when you grow up and you can do anything,'" she says. "He was 57 when he passed away, so he never even got to retire. His passing taught me how to live life because you never know how much time you have in life."
After traveling the world for a few years now, Kaye doesn't think she will ever move back to the United States.
"I'm just not interested in living in the U.S. I'm kind of used to a different quality of life," she says. "I like being able to live in towns where I can walk to get my groceries or walk to go to the doctor and just have an affordable cost of rent, food, entertainment, health care and the U.S. doesn't check any of those boxes for me anymore."
Kaye is currently on a break from overlanding and has stored her truck in Argentina, where it's currently winter. She plans to spend the summer in Bermuda, a country she considers home since she first visited at the age of 25.
"Everybody [in Bermuda] is so friendly and being social is a key part of life," Kaye says. "I just love living on an island and being able to go free diving or scuba diving. Bermuda is only 21 miles long and anywhere from end to end you can find a beautiful white sand beach. It's just a great place."