02/06/2013 11:26 am ET Updated Apr 08, 2013

Retiring Overseas Is An Art And A Science

A friend, Jeff, a Brit living now in Nicaragua, says that people ask him all the time why he chose to retire to that country over Costa Rica, a much better known and generally more highly regarded retire overseas choice.

"There are quantifiable explanations," Jeff says. "The cost of living in Nicaragua is lower than that in Costa Rica, for example. And Nicaragua has a program of special benefits, tax breaks, etc., for foreign retirees that's very competitive.

"But those aren't the reasons I recommend Nicaragua over its neighbor to the south to anyone who asks or why I chose to focus my time and attention in Nicaragua years ago, when I could as easily have based myself in Costa Rica.

"Nicaragua simply appealed to me more," Jeff explains, "for reasons that I have trouble explaining."

I know what he means. I visited Costa Rica for the first time more than 25 years ago. I've returned probably 25 times since. Its Pacific coast is beautiful, as is its mountainous interior. Great surfing, great bird-watching, great boating, great fishing...Costa Rica has all these things. When I first traveled to this country, it was also very affordable and boasted the world's premier foreign retiree program. Still, I didn't get it. I could list out the advantages and benefits of living in Costa Rica. I could make a great case for Costa Rica on paper. But I couldn't make myself want to live there.

Then, a few years later, I traveled to Nicaragua. I knew within a few hours of wandering around colonial Granada that this was a place I wanted to return to. This was a place I could call home, for visiting it for the first time felt like coming home.

The two countries share many similarities, and Nicaragua has the specter of the Sandinistas hanging over it. Still, it was Nicaragua, not Costa Rica that captured my heart. I was completely infatuated by this little country with such a troubled past, and I remain so. Every visit, I'm won over again. Everywhere I travel in Nicaragua, I find something that pleases me -- the red tile roofs and blue and white church steeples of colonial Granada... the glass-still surface of crater lake Apoyo as it appears from the deck of my little house on the mountainside...the barefoot children playing and laughing in Granada's central plaza...the sounds of the horses' hoofs as they pull their carriages along Granada's cobblestoned streets...

These things can't be quantified. You can't plug "classic colonial architecture" into a formula in a spreadsheet. But these can be the things that matter most. How will you know where in the world you should think about spending your time and your money? You'll just know. The French speak of the coup de coeur, the blow to your heart you feel at certain times in your life -- when, say, shopping for a new house. It's the sudden certainty that this place is it, this place is right. I'm a big believer in the importance of the coup de coeur when shopping for a new country, as well.

So, while, when you approach this how to retire overseas question, you should begin by taking a scientific approach, making lists and drawing comparisons, in the end, the decision where to launch your new life overseas is at least as emotional as it is intellectual or financial, for a place can make perfect sense in theory but appeal not at all in person.

That's why, at some point in your research process, you've got to get on a plane. Do the soul-searching to understand what you're looking for in your new life in retirement overseas. Identify the pluses and the minuses of the world's most appealing overseas retirement havens. Identify the two or three or four countries that could be the overseas Shangri-la you seek. Then plan an extended visit in each country you think might work for you, staying on, if possible, through the least-agreeable time of year -- the hurricane season, the rainy season, the peak tourist season, or the off-season, after all the tourists have gone home and nearly every shop, café, and restaurant in town has shut its doors until they return.

No amount of Internet research, reading, or planning can substitute for traveling around a place yourself. You've got to walk the streets, to watch the sunsets, and to meet the people. And, when you do, listen to your gut. Sometimes you'll know within 24 hours of arriving in a country. If you walk out on the street in a new place and feel safe, welcome, and comfortable, then that place could be for you.

We didn't choose Waterford, Ireland, for our first international move 15 years ago. It was chosen for us by my employers at the time. And we didn't visit for an extended time before we made the leap, because we didn't have time to. My husband, my daughter, and I visited for two two-week planning trips, once in July and again in September, then we arrived as full-time residents in Waterford in November.

The first couple of months living overseas is the honeymoon period. The people, the landscape, the view from your bedroom window are all new, exotic, and interesting. Nothing is cliché. You're fully occupied and engaged learning your way around and establishing yourself. After two or three months, though, your surroundings are more familiar. You've developed habits of day-to-day living, and you're able to relax a little. Suddenly, your new life isn't so much exotic and interesting as it is foreign and frustrating. You begin to miss the folks back home. By now you've made new friends in your new home, but your points of common interest are perhaps limited. They don't think like you. They don't talk like you. They don't do things the way you do them.

So it was for us when we moved to Waterford. By February, I was sad. Indescribably sad for no reason I could identify.

Then we took a trip to Nicaragua. After a few days on that country's sunny south Pacific coast, my sadness disappeared. What was going on?

The Irish winter. Though I'd traveled in Ireland for years, I'd never lived through an Irish winter. Some days, wintertime in Ireland, the sun rises after 9 a.m. and sets before 4 in the afternoon. In between the hours of 9 and 4, it's typically gray, drizzly, overcast, and damp.

Ireland can be a great place to call home, but before you commit to retirement in the Auld Sod, experience it in winter. Spend time in the country in January and February. Or don't. Ireland is one place that makes good sense as a part-time retirement haven. You could retire to Ireland each summer then spend your winters someplace bright and sunny. That was our strategy. After our first long winter in Waterford, we escaped to the tropics every December and returned to the Emerald Isle early March, just in time to appreciate Irish spring and summer.

The point is that you can't spreadsheet a new life in a new country. Retiring overseas is both a science and an art. The decision for if or where to relaunch and reinvent your life overseas at this stage should be made with your head, yes, but also your heart.

Earlier on Huff/Post50:

Fortune Magazine's 'Best Places To Retire Now'