Owning a Fun-Filled, Laidback Business Overseas

A few years ago, on a sunny Sunday afternoon, I was enjoying a beer at a local bar while I watched the football game. I was living in Costa Rica at the time—in the Pacific beach town of Tamarindo.

Being a sports fan and living outside the U.S. wasn’t a problem—all the games were shown live at the sports bar in the heart of town. They had a top-notch cable TV package and about eight screens in the place.

The guy on the bar stool next to me, sporting a football jersey and backward ball cap, was drinking a beer and watching the game intently. We talked a bit during commercial breaks. Then at halftime, he went behind the bar and started reviewing receipts at the register. Turns out this guy was the owner. And while his trusted staff ran the place, he was able to “supervise” while watching football.

Not a bad gig, huh?

Over the years, I’ve met many of these carefree entrepreneurs during my travels.

There was the property manager on the southern Pacific coast of Costa Rica who keeps a surfboard in his truck at all times so he can sneak away to catch some waves in between client meetings.

The B&B owner in San Miguel de Allende, Mexico who spends much of her day greeting guests, enjoying coffee (or a glass of wine) on the sun-splashed terrace, and coming up with new ways to decorate her establishment…and then heading into the local craft markets in search of that perfect decorative piece.

There was the couple in Peru with an adventure tour business in the Andes Mountains. They book mountain bike tours, hikes to ancient Incan ruins, jungle treks, and more. Of course, before they can recommend a new route or tour, they have to try them out themselves. And as avid mountain bikers and hikers…they don’t mind at all.

One of my favorites was a guesthouse and restaurant owner on Costa Rica’s Nicoya Peninsula. He starts his day with yoga…or surfing, if the waves are up. Late afternoon he strolls into his beachfront establishment—no shirt, no shoes, no problem—and cues up the music and chats with his staff as they mix tropical drinks for the guests sauntering in.

He isn’t getting rich. But he’s able to support his family and have exactly the lifestyle he wants. That’s not something he could do back home.

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