An Expat’s Biggest Regret (And How To Avoid It) In my 23 years of living overseas, I’ve never met anybody who hated their new home so much that they packed up and went home. What almost everybody has admitted to me, though, is that they wish they had done this sooner… that there are now…

No More Sleepless Nights Of all the investment options out there, why put your money into real estate? And, more to the point, why foreign real estate? My husband Lief Simon—who continues to grow his international real estate portfolio every year—says that diversifying into markets outside the United States helps him sleep better at night.…

11 Years Later, I’m No Longer The Crazy One… The first place I ever recommended Americans think about retiring overseas was Costa Rica. That was 35 years ago. A few years later I organized and promoted the first conference of my career, in San José. Thinking back, I have to give it to the 40-odd…

From Digital Nomad To Food Truck Chef—How To Fund Your New Life Overseas In your new life overseas, you could support yourself by going to work for someone else… but who wants a J-O-B? Better to make your own money and control your own schedule. Breaking from the 9-5 world opens you up to a…

If You Could Be Anywhere In The World Right Now, Where Would That Be? For the past week, Lief and I have been on lockdown with the rest of France. The rules aren’t as strict as in Italy. From our apartment in Paris’ 7th arrondissement, we can go to the supermarket or pharmacy. And, it’s…

Urgent: We’re Keeping The Dream Alive In A Time Of Crisis Last week, Lief and I traveled freely between Paris, France and Waterford, Ireland. Despite the spread of the coronavirus in both countries, it was business as usual for most people. In Waterford, we met with our Irish-based staff in a local co-working office space……

Boost Your Retirement Income With The Easiest Property Investment You Can Make Last week, as we opened up registration for our 2020 Global Property Summit, I talked about how to approach a property purchase overseas… and how the head and heart both come into play. But there’s one area that breaks this rule… where you don’t…

The Property Battle—Old Country House Vs. Return On Investment On the surface, buying an investment property overseas may seem like a straight-up business transaction. But things are rarely that clear-cut… I’ve hosted conferences on living, retiring, and investing in real estate overseas for more than 30 years. And, in my welcome address on the opening…

How Ecuador Offers You A Serious Lifestyle Upgrade Ecuador is the top place in the world right now to retire well on a very limited budget… Only a four-hour flight from the United States, a couple could live comfortably here for less than US$700 a month. That figure may seem unbelievable. But, if you’re a…

Medellin, Colombia—Much More Than Perfect Weather “Let me know when you start showing mild climates near lakes and I’ll consider it!” a reader wrote in this week. If you’ve read more than one of my dispatches, you know that I’m not here to present you with any one particular lifestyle. The year-round beach life of…