When Ian Douglass struck up a friendship with David Konwiser in grade school in Los Angeles, he didn’t realize it would change his whole life. David’s mother Cecilia is from Costa Rica and, when she saw how much Ian loved surfing and nature, she was adamant he visit her home country. After a decade of […]

If there is a silver lining to this dreadful pandemic, it might just be the work-from-home, work-from-anywhere revolution. Over the past year, companies have learned—much to their surprise, it seems—that workers are just as committed and productive outside of the confines of their cubicles. Meanwhile, workers have discovered a new, more flexible way of earning […]

“There is no way,” my childhood friend insisted, “that you’re earning 8.6% a year on a savings account.” That’s the way it goes with cryptocurrency—no one wants to believe you. So many have been so swayed by so much misinformation and misunderstanding from all manner of commentators that, at this point, they simply don’t trust […]

Time to hold myself accountable… Back in a letter to you in June, I explained my rationale for diving out of stocks. The pandemic was raging, the economy was sagging, unemployment was problematic, stimulus money supporting struggling families had an upcoming expiration date, and—perhaps most important—Wall Street was trading at irrational valuations. As I wrote […]

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 […]