• Lisa Desai moved her family of eight from Florida to Barbados.
• The mom said the kids have more freedom and independence living on the island.
• There are some cons, she added, but they are far outweighed by the pros.

This story is based on an interview with Lisa Desai, 46, founder and CEO of a facility management corporation that operates remotely in her adopted country, Barbados. It has been edited for length and clarity.

Our twins were approaching 14 when my husband, Ebrahim, 59, and I decided to move them and our four younger kids from Hutchinson Island North, Florida, to Barbados.

We were looking for an adventure before they hit 16 and took on responsibilities like getting a driver's license.

Ebrahim and I could run our facility management corporation, The Harmil Group, remotely, and we wanted a drastic change of scene.

We considered Thailand but were put off by the time difference, as we operate in Canada and the US and would be juggling separate schedules.

Greece and Italy seemed like slightly better options, but moving there involved a lot of bureaucracy.

Someone suggested Barbados

Then someone suggested to us, "Hey, why don't you try Barbados?" There was a $3,000 "welcome stamp" program for people who didn't work for a Barbados company and could show they had a certain amount of money in the bank.

It made perfect sense to us because it had super-reliable WiFi and an international airport from which you could fly directly to world cities like New York City and London.

We rented out our homes in Ottawa and Florida and arrived in Barbados on April 19, 2025. It was one of the best decisions of our lives.

I've homeschooled all six kids — now between 5 and 15 — since 2019, and there's a great homeschooling community here. We usually start at 7 a.m. and finish at 1 p.m.

Islanders are polite and friendly

Then we'll do something fun like go to the beach, go sailing, and play golf or tennis. The children are very independent, and we give them freedom to be themselves. Life in Barbados is the adventure we craved.

I don't think they'll fully appreciate it until they're adults, but the exposure to a new culture is very helpful.

Bajans are very friendly, polite, and open-minded. The kids are happy to chat with strangers and don't shy away from them.

Another advantage is the great healthcare system. It's inexpensive, and you get same-day or next-day service.

As for cons, the food can be expensive, and Amazon deliveries take between one and three weeks. If you want to buy something like a rashguard, you might visit five stores before finding the right size.

Transportation is a bit scary for me because it's the other side of the road, and the highways need maintenance. Infrastructure is in progress.

Everyone drives like they're in little go-karts. But you learn to go with the flow. You also need to adapt to island time, when a visit by a plumber arranged for 9 a.m. means sometime that day.

The kids' childhood is unusual

We visited Canada, where Ebrahim and I were raised, in the fall of last year, and it was nice to get some North American vibes. The kids spoke to their friends and family and came away thinking their childhood wasn't the norm.

We still have wanderlust, and our next journey may take us to Europe, but we'll always treasure our stay in Barbados.

"H

ow long have you been living in Singapore?"

It's a question taxi drivers have been asking me since I arrived from New York nearly 20 years ago.

In the beginning, the answer was small, just a year, then two.

My husband and I had come with a two-year plan. Freshly married, we told ourselves it was an exciting chapter in our new life together. We left boxes in the basement of my sister's Brooklyn apartment, assuming we'd be back for them soon.

But as the number crept past that deadline — five years, then 10 — those boxes slowly made their way over.

These days, it's not just taxi drivers asking how long we plan to stay.

My mom comments on how far away we live, now that it includes her two grandchildren. My in-laws gently remind us of the advantages of being closer. Everyone seems to assume there's a logical next stop, a final destination that will eventually make sense of everything.

But somewhere along the way, Singapore stopped feeling like a chapter and started feeling like muscle memory. I've lost my tolerance for cold weather after years in the tropics. Back in New York, walking into someone's apartment without taking off my shoes feels strange.

Still, there are reminders that my life is split across borders. As an American, I file US taxes every year — the US is one of the few countries that require it of citizens abroad — a constant reminder that I'm living between places.

My two kids look genuinely confused when someone asks them, "Where are you from?"

As more families build lives abroad, we're not the only ones being asked that question.

In 2024, about 3.3 million Americans were living overseas — a 15% increase since 2010 — according to a Federal Voting Assistance Program estimate that pieces together tax records, Social Security data, and foreign census figures. Because Americans don't have to register when they move abroad, there's no official count.

In this series, you'll hear from others who have made homes overseas, at different ages, for different reasons, and at different stages of staying, all answering the same question in their own way: Where is home, really?