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The Two-Country Retirement: Why Some Expats Don’t Move to the Philippines Full-Time

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For many people considering retirement in the Philippines, the decision seems enormous. Do you sell the house? Get rid of most of your possessions? Say goodbye to your familiar routines? Move thousands of miles away from children, grandchildren, longtime friends, doctors, and everything else you have known for decades?

It can feel as though there are only two choices: stay where you are or completely move your life to the Philippines.

But there is a third option that deserves more attention.

You can live in both.

Instead of permanently relocating to the Philippines, some retirees divide their year between the Philippines and their home country. They might spend four, five, or six months in the Philippines and the rest of the year back home. Others use the Philippines as their primary home but return to the United States, Canada, Australia, or Europe for several months each year.

For the right person, this two-country retirement can provide many of the benefits of living in the Philippines without requiring you to completely give up the life you already have.

It isn’t necessarily the cheapest way to retire, and it comes with complications of its own. But before you decide that retiring in the Philippines requires making one enormous permanent move, it is worth considering whether living between two countries might actually suit you better.

Retirement Doesn’t Have to Mean Choosing One Country

People tend to think about retirement relocation in permanent terms.

You retire in Florida. You retire in Arizona. You retire in Mexico. Or you retire in the Philippines.

But retirement gives you something your working years usually did not: control over your calendar.

If you no longer have to report to a workplace every Monday morning, there may be no reason you need to spend twelve months of every year in the same place.

Imagine spending part of the year in the Philippines enjoying warm weather, beaches, inexpensive restaurants, domestic travel, and a different pace of life. Then you return home for several months to see family, attend birthdays and holidays, visit longtime doctors, handle financial or administrative matters, and reconnect with the life you left behind.

When you’re ready, you go back.

The question changes from “Where am I going to live for the rest of my life?” to “Where do I want to spend the next six months?”

For some retirees, that is a much easier question to answer.

What Could a Two-Country Retirement Look Like?

There isn’t one correct schedule.

One person might spend November through April in the Philippines and May through October in the United States. Another might spend eight months in the Philippines and four months back home. Someone else might divide the year into several shorter stays.

A simple example could look like this:

November through April: Philippines

Spend six months based in Cebu, Dumaguete, Iloilo, Subic, Bohol, or another city you enjoy. Rent a furnished condo or apartment rather than maintaining a large permanent residence. Take weekend trips around the Philippines and perhaps use your location as a base for traveling elsewhere in Asia.

May through October: United States

Return for summer and early fall. Spend time with children and grandchildren, see friends, schedule routine medical appointments, take care of paperwork and enjoy the things you still love about home.

Then, as colder weather approaches, return to the Philippines.

That’s only one example. The important part is realizing that you can design the calendar around your life instead of designing your life around one location.

You Don’t Have to Say Goodbye to Your Family

This may be the biggest advantage.

Moving to another country can sound exciting when you’re thinking about beaches, warm weather and lower living costs. It can feel very different when your granddaughter has a birthday, your family gathers for Thanksgiving, a close friend becomes ill, or you realize you haven’t seen the people closest to you in eight months.

Video calls help. Social media helps. Cheap international messaging certainly helps.

None of those things completely replace being there.

A two-country retirement allows you to maintain a meaningful physical presence in both places. Your family knows you’re not disappearing to the other side of the world permanently. You’re simply spending part of the year somewhere else.

That distinction can also make the decision easier for the retiree.

You aren’t necessarily leaving your old life behind.

You’re adding another life to it.

It Can Also Help With Healthcare

Healthcare deserves serious consideration when planning any overseas retirement.

The Philippines has excellent physicians and good private hospitals, particularly in major cities, and many expats are comfortable receiving routine and even significant medical care there. But retirees may still want to maintain relationships with doctors and specialists in their home country.

For Americans, there is another important consideration: Medicare generally doesn’t cover healthcare received outside the United States except in limited circumstances.

A retiree dividing time between the two countries might schedule annual physicals, specialist appointments, certain procedures and other routine care during the months spent in America while maintaining local healthcare options in the Philippines for care needed while there.

That doesn’t eliminate the need to think about insurance and medical emergencies in the Philippines. You still need a plan for what happens if you become seriously ill while overseas.

But having a predictable period every year when you’re back in your home healthcare system may provide additional peace of mind.

Social Security Doesn’t Require You to Sit in America

Another common concern is whether moving overseas means losing Social Security.

For most American retirees who meet the applicable requirements, Social Security retirement benefits can continue while living outside the United States. The Social Security Administration provides a Payments Abroad Screening Tool specifically to help beneficiaries determine how their individual situation is treated.

That means your retirement income doesn’t necessarily have to stop at the border.

Your Social Security payment can continue while you’re enjoying breakfast in Cebu, walking along the boulevard in Dumaguete or watching the sunset in Panglao.

Of course, individual circumstances vary, particularly for non-U.S. citizens and people receiving certain types of benefits, so this is something to verify before making the move.

But You’ll Still Have U.S. Tax Responsibilities

Living part of the year—or even the entire year—in the Philippines doesn’t automatically remove an American citizen from the U.S. tax system.

U.S. citizens generally remain subject to U.S. income-tax filing rules on their worldwide income while living abroad.

A two-country lifestyle can actually make tax planning more important because you may have questions involving residency, state domicile, foreign bank accounts, investment income, retirement withdrawals, and possibly income earned while overseas.

The solution isn’t to be afraid of living internationally. It is simply to include taxes in the planning process rather than discovering the rules after you’ve already moved.

Before beginning a two-country retirement, a conversation with a tax professional familiar with Americans living abroad can be money well spent.

The Philippines Can Become Your Base for Seeing Asia

There’s another benefit that doesn’t receive enough attention.

Look at a map.

From the United States, visiting Japan, Thailand, Vietnam, Malaysia, Singapore, Indonesia, Taiwan, or South Korea can involve an expensive trans-Pacific journey.

From the Philippines, you’re already in the neighborhood.

A retiree spending several months each year in the Philippines doesn’t have to remain in one condo for the entire stay. The Philippines can become a base for exploring a part of the world that might have been difficult to experience during your working years.

One year you might spend a week in Vietnam. Another year, visit Japan. Take a long weekend in Taiwan or Singapore. Explore another Philippine island you’ve never seen.

Retirement becomes more than moving somewhere cheaper.

It becomes an opportunity to experience a larger world while you’re still healthy and active enough to enjoy it.

There Is a Financial Catch

Maintaining a life in two countries can cost more than simply moving to the Philippines permanently.

You have to consider airfare. You may be paying for housing in two places. You could have insurance costs in both countries. You might need storage. You may continue paying for a vehicle back home that sits unused for months.

Those expenses can quickly erase some of the savings that attracted you to the Philippines in the first place.

Housing is usually the biggest question.

Maintaining a $2,000-a-month home in the United States while also renting a $700-a-month condo in the Philippines changes the economics considerably.

But there are alternatives.

Some retirees downsize dramatically in their home country. Others keep a small condo or inexpensive apartment. Some stay with family during their months back home. Others maintain the Philippines as their primary residence and use short-term rentals when returning home.

The financial question shouldn’t simply be:

“Is the Philippines cheaper?”

It should be:

“What does maintaining my entire two-country lifestyle cost over twelve months?”

That’s the number that matters.

Two Homes Also Means Two Sets of Responsibilities

There’s another practical problem.

Someone has to watch things while you’re gone.

If you own a home in America, who checks it while you’re in the Philippines? Who notices a leaking pipe, storm damage or a broken furnace?

The same issue exists in reverse if you maintain a permanent residence in the Philippines.

Then there are vehicles, mail, banking, insurance, prescriptions, taxes, utilities, phone numbers and dozens of small administrative responsibilities.

None of these problems are impossible to solve. Millions of people live between countries.

But successful two-country living usually involves simplifying your life rather than trying to maintain two complete versions of it.

The fewer possessions and obligations tying you to each location, the easier the lifestyle becomes.

Renting May Make More Sense Than Owning

This is one reason renting can be particularly attractive for part-time Philippine residents.

If you’re spending five or six months each year in the Philippines, do you really need to own property?

A furnished rental can give you flexibility.

Spend one year in Cebu. The next year try Dumaguete. Maybe you discover you prefer Iloilo. Perhaps eventually you decide Subic fits you better.

You’re not locked into a property while you’re still figuring out what kind of Philippine life you actually want.

Renting also makes it easier to change your schedule. If family circumstances require you to spend more time at home one year, you aren’t paying for an empty Philippine residence for months.

For someone testing a two-country retirement, flexibility may be worth far more than ownership.

The Biggest Benefit May Be Psychological

There is something else happening here that has nothing to do with money.

A permanent international move can feel frightening because the decision seems irreversible.

Selling your house, selling your car, giving away possessions and moving 8,000 miles away creates enormous psychological pressure.

You naturally wonder:

What if I hate it?

A two-country retirement removes much of that pressure.

You’re not committing to living in the Philippines forever.

You’re committing to living there until your return flight.

If you love it, come back next year.

If you eventually want to spend nine months there instead of six, do that.

If after three years you decide the Philippines has truly become home, perhaps then you make the permanent move.

And if you discover that you prefer visiting the Philippines rather than living there, that’s valuable information too.

You haven’t failed.

You’ve learned what kind of retirement actually makes you happy.

It May Also Prevent the Expat Honeymoon Problem

We’ve talked before on Philippine Living Guide about the honeymoon phase of moving overseas.

Everything initially feels new and exciting. Eventually the Philippines becomes ordinary life. Traffic becomes annoying. Noise bothers you. You miss certain foods. You miss family. Little frustrations begin accumulating.

Leaving for several months can reset your perspective.

You return home and enjoy the conveniences you missed.

Then something interesting may happen.

After a few months, you start missing the Philippines.

You miss the warmth. You miss the people. You miss inexpensive restaurants. You miss the ocean. You miss the neighborhood where people recognize you.

Suddenly you’re looking forward to returning.

For some people, alternating between two countries prevents either place from becoming something they simply take for granted.

There Are Downsides

This lifestyle isn’t for everyone.

International flights become less enjoyable as you get older. Maintaining relationships in two countries takes effort. You can occasionally feel as though you belong completely in neither place.

Healthcare becomes more complicated. Taxes and paperwork can become more complicated. Maintaining two homes can become expensive.

There is also the possibility that your ability to travel changes.

A two-country lifestyle that works wonderfully at 65 may become exhausting at 78.

That’s why your retirement plan should be allowed to evolve.

Perhaps you spend six months in each country during your 60s. Later, the Philippines becomes your primary home. Or perhaps you eventually return permanently to your home country.

Retirement doesn’t have to follow the same plan for thirty years.

Who Is the Two-Country Retirement Best For?

This approach may work especially well for someone who loves the Philippines but still has strong family connections at home.

It can also make sense for someone who wants access to both healthcare systems, enjoys international travel, doesn’t mind flying, can comfortably afford the additional transportation and housing expenses, and values flexibility more than putting down permanent roots immediately.

It may be particularly attractive to someone who is intrigued by retiring overseas but keeps hesitating because the move feels too permanent.

You don’t necessarily have to make that decision yet.

Try It Before You Build Your Life Around It

Before buying property, shipping possessions or reorganizing your entire financial life, consider testing the idea.

Spend two or three months in the Philippines.

Go home.

Then come back for a longer stay.

Don’t spend the entire visit behaving like a tourist. Rent an apartment. Buy groceries. Do laundry. Go to the dentist. Deal with traffic. Spend some evenings doing absolutely nothing.

In other words, practice living there.

Then return home and notice how you feel.

Are you relieved to be back?

Or, after a few weeks, are you already thinking about your next flight to the Philippines?

Your reaction may tell you more than any retirement article ever could.

You Don’t Have to Choose

The traditional retirement question is:

“Where should I retire?”

Maybe that’s the wrong question.

A better one might be:

“Where do I want to spend my time?”

For some people, the answer will be the Philippines.

For others, it will always be home.

But there is another group whose answer may simply be:

Both.

You can spend part of the year near your children and grandchildren and another part watching sunsets in the Philippines. You can keep important connections to your home country while building new friendships and experiences overseas.

Eventually, you may decide which place truly feels like home.

Or perhaps you never will.

And maybe that’s perfectly fine.

The goal of retirement isn’t to prove that you successfully moved to another country.

The goal is to build a life you actually want to live.


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