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Live the Life You Love – Three Year Road Trip

Live the Life You Love – Three Year Road Trip

Several years ago, I had a friend who was on the cusp of an early retirement, while going through a rough breakup with her long term, angry boyfriend. She had decided to sell her house and move away. But to where? She had no idea. She was set financially, but was really struggling.

At one point during our conversation, she asked me what she was going to do. I said, “You’re going to live out of your car.” She almost fell off her chair. “What?!” She demanded. I repeated it. “You’re going to live out of your car.”

“How? Why?” She stammered.

I continued. “You’re going to put all of the stuff you want to keep in storage, you’re going to pack the clothes you like into a few suitcases, you’re going to identify the top five places you think you’d like to live, you’re going to get into your car and drive to first one. You’re going to find a nice bed and breakfast and stay for at least a week.” She just looked at me wide eyed, “Then what?” she asked.

“Then, you’re going to drive to the second one. Then the third. You’re going to note what you like at each place, compile a list of top characteristics you need in a home and in a location. You’re going to keep traveling and identifying spots until you find one you love.” She was still in shock. “Look,” I said. “If I can do it, you can do it. If I can travel, and run my business from the road, you certainly can live out of your car.”

“But, I’m not … I don’t have … I’m not a computer person like you, Zurich.”

“But you’re a f***ing (I used her last name), and I thought that meant you could do anything! Isn’t that what you dad taught you?!”

This got her out of her funk a bit. Her dad had said that. It had served her well. Though they certainly weren’t famous, she was part of that family that had pride in its name, wasn’t she? Maybe this wasn’t impossible.

I continued, “This afternoon, we’re going to take you over to the cell store. You’re going to get a mobile hotspot so you can have internet on the road. Were going to get you a new cell phone. We’re going to get you all connected. Then you’re going to hit the road.” I really don’t think she believed it was possible until we showed up at the cell phone store and I showed her how online banking worked, how to use the modem on her phone and laptop, how to use various travel sites.

“You’re really serious, aren’t you?” She asked.

“Look,” I said, “there’s nothing left for you here, really. You have family in different parts of the country you like, you’ve talked about living elsewhere, now’s your chance. Obviously, I told you to live out of your car for shock value, because that was fun to see you nearly fall off your chair, but there’s nothing wrong with being a vagabond for a bit. You have money. You have time. You don’t have any debt. You have a brain and a sense of adventure. Stay in nice places, no two star hotels for you. You’d have to spend more than $9,000 a month to go broke.”

“Oh my God! $9,000 a month? I could never spend that much.” She exclaimed.

“Well, there you go then. Go be homeless and keep in touch.”

And you know what? She actually did it. For three years she was homeless, living out of her car, using an online mailing service, on her way to find a new home. She’d call me from the road, usually telling me how she had thought I was totally nuts when I told her to be homeless, but that she really enjoyed the freedom of the open road. She wasn’t living high on the hog because that wasn’t her style, but she liked her adventure. As the months went by, she’d call me from some new location to tell me about a house she liked, we’d talk about it, compare it to her list or comments she’s made and she’d move on.

About three years later, she eventually settled on the Gulf Coast of Florida. Coincidentally, and unknowingly, I ended up less than a mile from her, seven years later, after my own exhaustive nationwide search. She still tells the story about how I told her to live in her car, and how much she appreciated me just giving her the push that she needed.

St. Croix, U.S. Virgin Islands