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 […]

Do you remember when a basic savings account actually generated a bit of coin?  I just checked: The last time we could earn anything north of 5%—the threshold most savers used to consider “solid income”—was the summer of 2007. Crazy to think that was more than 13 years ago. In those intervening years, we’ve become […]

In early adulthood, Lee Nyhus, now 59, was stricken by wanderlust. The Chicago native traveled extensively to less-visited corners of the globe, including spending a year backpacking around Africa. Even when it came time to settle down for a while, she chose what was, at that time, a somewhat unusual destination for American expats: Tokyo.  […]

In the weeks and months following COVID’s emergence in the U.S., I began writing about the toll it was having and would have on older workers—namely the historically high unemployment rate for people, like me, who are over 50. Now comes more sad news. In the third quarter, more than 28 million baby boomers threw […]

As working from home becomes the new norm in the U.S. and around the world, many people are beginning to wonder why they should remain in expensive urban centers when they could just as easily work online from a more affordable, beautiful, and enriching destination overseas. Unsurprisingly, one of the most popular regions among workers […]

In 2010, Annelise Hagan accepted a position as science director for two marine parks in Belize. This job took her to Placencia, a narrow peninsula in the south of the country known for its palm tree-lined Caribbean beaches and spectacular diving.  “Placencia has the perfect mix of locals, expats, and tourists,” says Annelise. “And it’s […]

So, Eric Schmidt wants to be a Cypriot. Maybe you’ve heard of Eric, maybe not. He was a head honcho at Google for nearly two decades before he left this past May. Of course, that’s neither here nor there because what’s important about Eric Schmidt today is that last month he and his family earned […]

I lazily open my eyes, listen to the birds singing, and once again count my blessings. It’s nearly time to go to “the office,” but that simply means rolling out of my hammock, pulling a T-shirt over my bikini, and plugging in my headset for my online lessons. My current desk looks out over the […]