The Problem With Retiring Overseas is Deciding Where to Live

When my now-grown son was a little boy I used to take him to Baskin Robbins for a cone. He would stare and stare at those 31 flavors. They were all so tempting, and I watched him grow physically agitated as he agonized over his decision. Inevitably he would always pick—chocolate chip.

The same thing can happen now to folks scouring the Internet for possible retirement locations.

The Far East… Latin America… Europe… how do you narrow down your search? You could spend hours and go blind reading articles, blogs, and forums. But when some people say a place is great while others complain and can’t wait to leave, what have you really learned?

Four years ago, when I was doing similar research, the online universe looked much different. If anything I was suffering from “information underload.” There just wasn’t a lot of information out there compared to today.

My wife and I had created what we feared was an impossible wish list for our potential relocation:

  • Low cost of living
  • Ideal weather
  • Proximity to our family
  • Excellent medical care
  • Cultural activities and modern amenities

I was fortunate to stumble upon a city we’d never heard of in a small South American country we knew next to nothing about—Cuenca, Ecuador.

It appeared to satisfy all of our criteria, plus Cuenca reminded us of Charleston, South Carolina, a beautiful colonial city of similar size where we had the pleasure to live for six years.

We immediately booked a look-see trip, and several months later found ourselves wandering around Cuenca wondering if we could live happily in this faraway place. No red flags appeared, so a year later we stepped off a plane and began our new adventure in Ecuador.

“What?” you might ask. “You actually moved to the very first place you discovered a year after you found it? How did you do that?”

Yes, we did. But, you see, we already knew what we were looking for.

I find too many people suffer from “analysis paralysis.” Much like my son, they anguish over all the choices to the point of becoming immobilized.

Potential expats sometimes say to me, “I’m trying to decide between Cuenca and the coast.” I always reply that they can figure that out without leaving their living room at home.

What do you want to wake up to every day—crashing waves and hot, humid weather, or varied topography and cool mountain air? A laid-back lifestyle with few demands on your time, or lots of activities to keep you busy?

I encourage you to do some serious soul-searching and answer that one fundamental question for yourself. As you envision your ideal new home you’ll find that many of the so-called relocation “possibilities” suddenly eliminate themselves. Think hard about what is most important to you and write down your answers. Make your list as specific as possible.

Could my wife and I have found an even better spot than Cuenca if we had kept looking? Perhaps. But as my favorite philosopher once said, “When you’ve gotten the message, hang up the phone.”

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