My Life as a Remote Worker in Uruguay

Posted by The Savvy Retiree on January 28, 2021 in Remote Working

I moved from Washington State to Uruguay in 2006. For my first eight years or so in the country, I lived in Punta del Este, one of the foremost resort destinations in South America. During high season, the local airport in Punta fills with private jets, while the harbor is jam-packed with boats, including large […]

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Pocket up to $50 an Hour as an Online English Teacher

Posted by The Savvy Retiree on January 27, 2021 in Online Income

If you had complete freedom to transform your life, what would you do? Where would you live? How would you spend your days? Maybe you’d like to live next to a tropical beach so you could spend your mornings and evenings strolling barefoot on the sand. Or perhaps you’d prefer a house amid a lush […]

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The Easiest Way to Earn a Good Online Income

Posted by The Savvy Retiree on January 26, 2021 in Portable Incomes

My day usually starts at the ocean around sunrise, which this time of year, is right about 7 a.m. here on the coast of Oaxaca, Mexico. The sun sets about 11 hours later, and there’s nothing but sunshine in between. I can’t imagine a better environment. But my days weren’t always like this. Years ago, […]

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How to Be Good at Literally Anything

Posted by The Savvy Retiree on January 25, 2021 in Savvy Tips

You ever watch a movie and a character does something that literally makes you cringe—makes you feel uncomfortable, even though it’s only make believe? I had that moment recently while cataloging several screenplays I’ve written over the years. I currently have a script in play in Hollywood—a romantic comedy I finished over the holiday break. […]

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“Better Than a Maserati”—A Laidback Life in a Tropical Paradise

Posted by The Savvy Retiree on January 20, 2021 in Live Better

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 […]

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The Top 3 Digital Nomad Destinations in Costa Rica

Posted by The Savvy Retiree on January 19, 2021 in Remote Working

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 […]

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A Risk-Free Way to Buy Bitcoin (No, Seriously)

Posted by The Savvy Retiree on January 18, 2021 in Investing

“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 […]

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Confession Time: The Predictions I Got Right and Wrong Last Year

Posted by The Savvy Retiree on January 18, 2021 in Investing

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 […]

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I Travel the World as a Food Blogger…and You Could Do the Same

Posted by The Savvy Retiree on January 15, 2021 in Online Income

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 […]

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3 Steps for Turning Your Existing Skills Into an Online Income

Posted by The Savvy Retiree on January 12, 2021 in Online Income

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 […]

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Forget the 9-to-5—Get Ready for the 3-2-2…or Something Even Better

Posted by The Savvy Retiree on January 11, 2021 in Freelancing

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 […]

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The End of America…and What You Should Do About It

Posted by The Savvy Retiree on January 10, 2021 in Live Better

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 […]

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