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Don't Just Retire Abroad—Work There

Boomers find second careers in foreign lands

spinner image Dwight Stanford retired to Offida, Italy, where the 59-year-old co-owns and operates a B&B in a 500-year-old farmhouse and the Paolini & Stanford Winery.
Dwight Stanford retired to Offida, Italy, where the 59-year-old co-owns and operates a winery, as well as a B&B in a 500-year-old farmhouse.
Maryse Pen

When Dwight Stanford retired from his 25-year career as a surgeon in Kansas City, Mo., he headed to Italy, more specifically a hilltop town named Offida. It wasn't on a whim. In 2006, he'd fallen hard for the Italian way of life after earning a master's degree in food science during a sabbatical there.

Today, the 59-year-old co-owns and operates a B&B in a 500-year-old farmhouse, as well as the Paolini & Stanford Winery, which produces 25,000 bottles of organic wine a year. On any given day, he might be out driving a tractor or preparing breakfast for B&B guests with the help of his fiancée, Maryse Pen. And just recently, he's able to pay himself a small salary.

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For many people, his story may seem like fantasy. But retiring abroad and continuing to earn a paycheck has in fact become increasingly common.

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While the precise number of Americans working overseas is hard to nail down, over half a million people receive Social Security benefits in foreign countries, according to the Social Security Administration. And that doesn't count boomers like Stanford who aren't yet entitled to Social Security or have delayed taking it.

If working in a foreign land sounds appealing to you, here are some steps that can help make it happen.

1. Do your research. International Living magazine publishes an annual global retirement index that ranks the World's Best Places to Retire. For this year's 23 countries, which include Panama, Ecuador, Mexico, Costa Rica, Spain and Portugal, its researchers crunched numbers on the cost of living, health care, housing, internet access, infrastructure factors such as international airports and, of course, weather.

Another resource is the 2016 Annual Retire Overseas Index, from the online publication Live and Invest Overseas. This year's No. 1 place: the picturesque coastal region of Algarve, Portugal. International retirement expert Kathleen Peddicord and her team develop the annual ranking using statistics from public records, as well as sandals-on-the-street reporting by correspondents.

2. Leverage language. If you speak a foreign language, or just studied one in high school, it can make sense to focus on places where it's spoken. And keep in mind that your English skills can open the door to a wide range of work that includes teaching English, interpreting and guiding English-speaking tourists. You might land a job at a hotel, tourist-oriented art gallery, bistro, B&B, retail shop or real estate agency.

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For leads, check out, a popular website on living abroad. "Expat retirees typically move to warm, beachfront areas such as Ecuador, Panama, Costa Rica, the Philippines, Thailand, the Dominican Republic, Mexico and Belize," says founder Betsy Burlingame. "These areas are also popular tourist destinations, and expat retirees can often find work in businesses related to the tourist industry."

spinner image Dwight Stanford works in his vineyard in Offida, Italy after he retired.  Today, the 59-year-old co-owns and operates a B&B in a 500-year-old farmhouse and the Paolini & Stanford Winery.
The Paolini & Stanford Winery produces 25,000 bottles of organic wine a year.
Maryse Pen

3. Go for a lengthy visit. Before settling on a place, spend a couple of months there to see if you really fit in. Befriend local expats and learn what brought them there and what kind of jobs they might have. Do your own sleuthing by talking to local business people.

Understand the local employment laws. Find out if the country allows foreigners to hold the kind of job you want and whether a work permit is required. Also, gauge competition for the job you're seeking; supply and demand applies as much here as anywhere.

4. Seek out virtual employment. You don't have to pick a place to live based on the job market there. Turn what you've done your entire career into a virtual consulting or project assignment-based business that you can do online. It's the ultimate telecommute, provided you have a good internet connection.

5. Open a bricks-and-mortar business. This is more ambitious, but often it's doable. Patrice Wynne closed her independent bookstore, Gaia, in Berkeley, Calif., and retired with the goal of taking a break and enjoying the good life abroad. She discovered she wanted to keep working and remain creatively engaged.

So six years ago, Wynne, now 64, opened Abrazos Boutique San Miguel, a 650-square-foot retail shop in the historic center of the Mexican colonial city San Miguel de Allende. It sells vibrantly patterned fabric aprons, handbags and clothing sewn by local seamstresses. Today, she also sells her goods wholesale in boutiques around the world.

Hiring a bilingual person who can help steer you through operational challenges is essential for many expat small-business owners, Wynne says. Even if you're fluent in the language, you'll need a bilingual legal and tax adviser to grasp the ins and outs of applicable laws, employment regulations and business contracts.

6. Learn the local etiquette for business relationships. Slow down. Some deals don't get done until you've had a meal together. In Mexico, for instance, even a simple business phone call takes extra time. You need to ask about family, health and how the day is going.

7. Pay attention to taxes. If you're going to earn even a small salary, consult with someone who knows international tax issues. Both the United States and your new country of residence could try to tax the money you earn.

As a U.S. citizen or resident alien, you are taxed by the United States on your worldwide income. You're required to file an annual tax return with the IRS. However, you may be eligible for the foreign earned income exclusion, which in 2015 exempted $100,800 of income per person from U.S. taxes. And if your foreign bank accounts hold a total of more than $10,000, with certain exceptions, you must file a disclosure form with the U.S. Treasury by April 15.

Finally, be open-eyed about the drawbacks. Your internet connection might flicker in and out. Siesta time? Even your bank may shut its doors. Local bureaucrats might want a little pocket money as thanks for filing your business paperwork.

And of course there's the possibility you'll get homesick. There's a lot to be said for living in the USA. But more than a few people have found fulfilling second careers beyond its shores. You might become one of them.

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