How to Ease Yourself Into the Perfect Overseas Retirement

Editor's Note: This story originally appeared on Live and Invest Overseas.

This doesn’t have to be all or nothing. You could “retire overseas” and still spend part or even lots of your time back home.

I make the point in case it hadn’t occurred to you already.

The idea of moving to a new country, full stop, full-time, can be intimidating. Selling your current home … off-loading your car, your furniture, your lawn-care equipment … flying off to a new country where you know no one and where everyone you meet speaks another language?

Boiled down like that, this retirement overseas agenda can seem foolish, maybe even terrifying.

So don’t sell your home. Keep your car if you like it. Lock the lawn mower in the garage. Pack a few bags and head off to someplace that’s got your attention for, say, a month or two.

Don’t even think about buying a house or anything else. Rent small and modest. Or arrange an extended stay in a B&B or guesthouse.

Keep things low-key and low-pressure.

Planning your retirement overseas doesn’t have to be like jumping off a cliff. Here’s how it can work.

You can ease into the idea

Then, if you find the place you take for a test spin disappointing in some way, you can return home (remember, your car’s waiting for you in the driveway) … and begin planning your next “retire overseas” holiday. Give someplace else a chance.

You could continue like this for years. You’d be enjoying some of the benefits of a new life in a new country (a maybe dramatically reduced cost of living, better weather, more affordable medical care, new friends, grand adventures, plus little luxuries you probably can’t afford now — maybe full-time household help, for example), but you’d have a safety net.

What you’ll find is that, with each retire-overseas foray, your confidence will build. And your plan will evolve.

Next step: maybe extend the length of each retire-overseas vacation

You could spend a few months at a time in each new place, depending on the jurisdiction’s residency restrictions, thereby avoiding the visa issue.

You could begin renting out your place back home when you’re not using it. This income would help to subsidize the expense of your overseas retirement wanderings.

You could eventually invest in new digs in a place you decide you like well enough to want to return to regularly. Again, rent out this apartment or beach house when you’re elsewhere to further supplement your retirement income.

Maybe, eventually, you find you’re ready to sell your place back home

As time passes, your connection there seems less and less important. More interesting are the new places you’re discovering, the new friends you’re making, the new adventures you’re having.

Take it one step at a time and let your overseas retirement plan develop organically. Just as there’s no one-size-fits-all overseas retirement haven, neither is there a retire-overseas plan that suits everyone. This idea is infinitely customizable.

Many people have been where you are

I’ve been covering this beat for more than 35 years. Over the decades and the many thousands of people I’ve spoken with personally, I’ve been struck by the diversity of situations.

One couple might be looking for a place at the beach where they can spend two or three months at a time … then return home to spend time with grandchildren.

Another is looking to build a portfolio of second homes where they could escape now and then but that would also generate good yields over time.

One single lady is interested in snow-birding it in the tropics because she’s had it with shoveling snow each winter.

Another wants to clean-slate it, sell everything she owns right now and start over, full-time, someplace new and exciting. Total reinvention.

Each agenda makes sense in context. And yours will be your own.

My point is that you don’t need to determine now or even before you set out exactly what your new life overseas will look like.

You don’t need to make a plan for retiring overseas full-time, full stop.

Keep it simple. Take a trip.