For almost five years, I’ve been earning a living online and traveling the world through blogging. In that time, I’ve visited more than 60 countries across five continents, all the while working with companies, brands, and tourism boards to promote services and destinations that I believe would be favorable to my audience. I’ve worked with […]

Despite the massive boom in freelancing, many baby boomers and Gen Xers still have the impression that developing an online income is unrealistic or somehow out of reach for them. Their thinking goes that you need to have advanced skills in a technical field like programming or web design to build an online income. But […]

Harvard thinks that the 9-to-5 is dead—that we’re heading for a 3-2-2 world. I think Harvard’s on the right track, just a bit off with the math. The way I see it, we’re heading for 24-7. Some of us, in fact, are already there. And I can tell you from experience, it’s a good place […]

I was born on Jan. 27, 1966. In a few weeks, I’ll be 55. I’ve seen firsthand a lot of the events that defined the U.S. over those intervening years. But Jan. 6, 2021…that’s the day America as I know it ended. Let’s call it Insurrection Day. Understand that what I am about to write […]

Expats around the world are an enterprising bunch, and perhaps nowhere is this more apparent than in France. When you’re surrounded by so much natural beauty, and some pretty amazing food and wine to boot, you tend to want to stick around. I’ve been able to carve out a niche for myself by working as […]

In 2006, Jennifer Choban moved from Portland, Oregon to Guanajuato, Mexico. She’d gotten divorced about a year before and was looking for a change of scenery and a renewed sense of adventure. So, when a coworker told her she was buying a house in Guanajuato, “I suggested to her that I take care of it,” […]

U.S. expat Bill Cotter was drawn to Costa Rica’s southern Pacific coast by his love for surfing and his desire for a more laidback, nature-filled life. The unspoiled, biodiverse region, which includes beachfront communities such as Dominical, Uvita, and Ojochal, combines affordability and spectacular scenery with modern infrastructure and amenities. This helps explain its growing […]

Arthur Ashe, the famous tennis champion, offered a quote that, to me, rings so true for baby boomers and Gen Xers who want to begin freelancing online: “Start where you are. Use what you have. Do what you can.” Ashe may have uttered those words long before the online gig economy became popular, but they […]

My love affair with Costa Rica started 20 years ago. Trudging through the snow in Boston to the office of my first job, I peered into a fogged-up travel agent’s window and saw an ad for a last-minute tour to Costa Rica. It was my first and last organized tour—I hated being on someone else’s […]

Do you dream of living in another country long enough to truly explore the depths of its culture, but haven’t figured out a way to do it without draining your bank account? If you answered “yes” to that question, then I have the solution for you. It’s one of the best ways to earn abroad, […]

At the moment, the U.S. is home to about 18.6 million millionaires. If every one of those millionaires wanted to buy just one bitcoin…they couldn’t. There aren’t enough bitcoins to go around. There’s a bigger lesson there that we’ll return to in a moment. Here in the 21st century’s third decade, we—society, writ large—sit on […]

For decades, Costa Rica has drawn enterprising expats and part-time retirees who want to earn an income while enjoying a relaxing, affordable life overseas.

Country #68. Montenegro. I’m here to get married—well, actually, I am already married as you read this. We—my partner, Yuliya, and I—are down on the Adriatic coast, in the quaint seaside town of Budva. We’ve been here only a few days, but I can assure you we’ll be back. This is a beautiful, mountainous country […]

Dropshipping is one of the most accessible ways to become an online entrepreneur and build a new income you control. As the owner of your own dropshipping store, you can work from anywhere, choose what you sell, and set your own prices. In time, you could potentially even build your store into a brand and […]

“Right now, I feel blessed. I’m doing what I want, where I want, when I want,” says Ellen Makleroy. The Florida native is sipping an iced coffee surrounded by video and photography gear on the shaded deck of the Zanook wakeboarding park outside of Bangkok, Thailand. Behind her, wakeboarders are jumping ramps and doing tricks […]

Here at the end of the year, I have a number to share with you: $44,358. That’s my total, pre-tax haul from all my various freelancing activities in 2020: financial columns, writing walking tours, editing screenplays, the screenplay for which I sold the rights, microstock photography, income from an e-book I wrote, a bit of […]

More than two decades ago, retired businessman Sidney Richardson traded a high-pressure career in the property and insurance sector for the sunny beaches and relaxed lifestyle of the Algarve in southern Portugal. With 300 days of sunshine a year, stunning beaches, and world-class golf, the Algarve is now an internationally renowned tourist and expat destination. […]

I set up my tripod in a sunny patch between two trees, excited to capture this gorgeous day on my smartphone camera. There’s lush foliage all around me…old-growth trees, flowering shrubs, a variety of grasses in a variety of colors.  The sky is an intense cornflower blue, and there’s a faint scent of frangipani in […]

Finally—a remote-worker incentive plan that actually makes a lot of sense. Greece! I’m sure you’ve seen in recent months all the Caribbean locations that are offering special visas to Americans (and others) who want to live and work from the beach as digital nomads. That’s all well and good, and the Caribbean is certainly a […]

“Where’s the best place to live as a remote worker?” I regularly hear some iteration of that question from friends and acquaintances, so I thought I would answer it today in light of new research out of Upwork, the freelance website I regularly write about. The company surveyed a bunch of Americans and concluded that […]

Let me start by saying that I have no natural aptitude for languages. I’m a 59-year-old retired police detective who still has vivid memories of trying, and failing miserably, to learn French in high school. But once I retired, my wife and I thought we’d like to travel to warmer climes during the bitterly cold […]