As someone who helps people redefine what retirement can be, I’ve seen firsthand how this stage of life is evolving. For years, retirement was thought of as a time to slow down and settle into a quieter routine. But today, a new vision is emerging—one filled with adventure, purpose, and fresh opportunities.

Instead of stepping away from work entirely, many retirees are embracing a more flexible lifestyle, working remotely while exploring the world. This growing movement, often called the “great unretirement,” is proving that retirement isn’t about winding down—it’s about designing a life that truly excites you.

For many, this means a lower cost of living, new adventures, and the flexibility to keep earning on their own terms. But is it the right move for you?

Retiring overseas while working remotely can be an exciting way to stretch your savings and keep life interesting. But it also comes with challenges.

Let’s take a closer look at what to consider before making the leap.

1) cost of living matters

One of the biggest reasons people retire overseas is the cost of living. In many countries, you can enjoy a comfortable lifestyle for a fraction of what it costs back home.

Lower rent, cheaper groceries, and affordable healthcare can make your retirement savings last much longer. And if you’re working remotely, your income may go further than ever before.

But it’s not just about saving money. It’s also about quality of life. Some places offer great weather, a slower pace, and a vibrant expat community—all at a lower cost.

Still, it’s important to do your research. Not every destination offers the same financial benefits, and exchange rates or unexpected expenses can impact your budget.

2) healthcare can be a game-changer

Of course, every country is different. Some places have excellent public healthcare, while others require private insurance. It’s important to research options before making the leap.

 Having security and peace of mind with regard to access to healthcare when you’re working remotely in retirement,  can make all the difference.

3) visas and taxes aren’t always simple

Moving abroad isn’t just about packing your bags and booking a flight. Many countries have specific visa requirements for retirees and remote workers, and the process can take time.

Some places offer special visas for digital nomads or retirees, allowing long-term stays with minimal hassle. Others require proof of income, health insurance, or even a certain amount of savings in the bank.

Taxes can be another challenge. Depending on where you move, you might still owe taxes back home, even if you’re living abroad full-time. The United States, for example, taxes its citizens no matter where they live, though treaties in some countries can help reduce double taxation.

Before making the move, it’s important to understand the legal and financial side of things—so there are no surprises down the road.

4) cultural differences take time to adjust to

Living in a new country isn’t the same as being on vacation. Daily life comes with cultural differences that can be exciting—but also challenging.

Simple things, like how people communicate, how businesses operate, or even how long it takes to get things done, can feel unfamiliar at first. In some countries, a slower pace of life is the norm, which can be frustrating if you’re used to efficiency and quick service.

Language barriers can also play a role. Even in places where many people speak English, not knowing the local language can sometimes make things more difficult, especially when dealing with government offices or medical care.

Over time, though, these differences often become part of the adventure. Learning the local customs and embracing new ways of doing things can make the experience even more rewarding.

5) loneliness can be an unexpected challenge

Moving to a new country can be exciting, but it also means leaving behind family, friends, and familiar routines. At first, everything feels new and interesting, but after a while, the reality of being far from home can set in.

Building a new social circle takes effort. It’s not always easy to make friends in a different culture, especially if you don’t speak the language fluently. Some days can feel isolating, even in a beautiful place.

Technology helps—video calls, messages, and social media make it easier to stay connected—but it’s not the same as grabbing coffee with an old friend or attending family gatherings.

Finding a community becomes essential. Whether it’s through local events, expat groups, or even coworking spaces, having people to share the experience with can make all the difference.

6) time zones can make remote work tricky

Working remotely from another country sounds like a dream—until you realize your meetings are at 2 AM.

Time zone differences can create challenges, especially if your job requires real-time collaboration. While some remote roles offer flexibility, others still expect you to be available during specific hours, which might mean working late nights or early mornings.

Even communication can slow down. If your team is asleep while you’re working, simple conversations that would take minutes in an office might stretch over days.

Before making the move, it’s important to consider how your work schedule will line up with your new location. For some, the trade-off is worth it, but for others, the time difference can be a dealbreaker.

7) flexibility is the key to success

No matter how much planning goes into retiring overseas and working remotely, unexpected challenges will come up. Visas may take longer than expected, internet connections might be unreliable, and the reality of daily life in a new country won’t always match the dream.

Being able to adapt makes all the difference. Some places might not feel like home, and that’s okay—moving again is always an option. Plans can change, jobs can evolve, and what works today might not work a year from now.

The people who thrive in this lifestyle aren’t the ones with perfect plans but the ones willing to adjust as they go.

bottom line: it’s not for everyone, and that’s okay

The idea of retiring overseas while working remotely is appealing for many reasons—lower costs, new experiences, and the freedom to design life on your own terms.

 There are amy people who have successfully done this. It requires adaptability, patience, and a willingness to navigate unfamiliar challenges. The reality is that it’s not just an extended vacation. Some people thrive in this lifestyle, while others find themselves longing for the familiarity of home.

There’s no right or wrong answer—only what works best for you. The most important thing is knowing yourself well enough to decide whether the adventure is worth the trade-offs.