13 Questions to Ask Yourself Before Moving Abroad

An honest self-check from a team that made the move to Costa Rica and now helps others do the same.

Should I move abroad? Only if your reasons survive honest questioning. Before you sell the house and book the flight, work through the 13 questions below. They cover money, visas, healthcare, family, and daily life. We have lived in Playas del Coco, Costa Rica for years, and we have watched these questions predict who stays and who leaves.

We are not here to talk you into anything. Roughly half the people who tell us they are moving abroad never do, and some who do move go home within two years. The ones who stay tend to have already answered these questions before they arrived. Treat this as the first page of your moving abroad checklist.

1. Why do I actually want to move abroad?

"I hate winter" and "I need a change" are feelings, not plans. Push one level deeper. Are you chasing a lower cost of living, a slower pace, adventure, or distance from something painful? Moves built on running toward something tend to last. Moves built only on running away often do not, because your problems fit neatly in a suitcase. Write your real reasons down. You will reread them on a hard day, and there will be hard days.

2. Have I spent real time there, outside vacation mode?

A week at a beach resort tells you almost nothing. Come for a month or more, rent a normal house, cook, shop at the local grocery, sit through a power outage, and visit in the low season. In Guanacaste that means seeing both the dry season and the rainy months of September and October. If you still love the place after paying a utility bill and waiting in line at the bank, that is real information.

3. Can I actually afford the life I am imagining?

Moving abroad can lower your costs, but it is not automatic. Imported goods, cars, and beach-town restaurants can cost as much as home or more, while local produce and labor cost less. Build a real budget line by line instead of trusting headlines. We wrote an honest breakdown in our guide to the cost of living in Costa Rica. Then add a buffer, because the first year always costs more than you planned.

4. How will I fund my life, and what about taxes?

Whether you live on a pension, savings, remote work, or rental income, know the plan before you land, not after. If you are a US citizen, remember that the IRS still requires you to file and report your worldwide income even while living abroad. Other countries have their own rules layered on top. Talk to a cross-border accountant before you move. It is far cheaper than untangling a mess later.

5. What is my legal path to staying?

Tourist entry is not a residency plan. In Costa Rica, for example, the US State Department notes that immigration authorities may allow visitors to stay up to 180 days, but it is not guaranteed. Long term, most expats apply for a residency category tied to pension income, stable income, or investment. Requirements and amounts change, so confirm the current rules with a licensed immigration attorney. We covered the entry rules in our post on the 180-day tourist stay.

6. How will I handle healthcare?

This is the question people under 50 skip and people over 60 obsess over. Both are wrong. Research the public system, private hospitals, and what your current insurance will and will not cover overseas. Ask where the nearest emergency room actually is. In our area, private clinics handle everyday care locally and serious cases go to Liberia or San José. Price out private insurance for your age before you commit, not after.

7. Can I handle being far from the people I love?

Grandkids, aging parents, weddings, funerals. Video calls help, but they do not hug back. Be honest about how often you will realistically fly home, what that costs, and how you will feel when something happens and you are a flight away. Some of our happiest clients split the year in halves. Some of the saddest departures we have seen were not about money at all. They were about missing people.

8. Will I learn the language, or at least try?

You can get by in many expat towns with English, including ours. Getting by is not the same as belonging. Even clumsy Spanish changes how the community treats you, what you pay, and how problems get solved. You do not need to be fluent. You need to be willing to be bad at it in public, week after week. If that idea makes you cringe, think hard about how isolated you might feel.

9. How do I react when things are slow or broken?

Somewhere new, the internet will drop, a road will flood, and a repair that takes a day back home will take three visits. If your instinct is to demand efficiency, you will be miserable, and you will make the locals around you miserable too. If you can shrug, laugh, and build slack into your plans, you will do fine. We listed the frustrations honestly in 10 reasons to reconsider moving to Costa Rica.

10. Should I rent first or buy right away?

Rent first. We say this as a company that sells real estate. Renting for six to twelve months lets you test neighborhoods, seasons, and noise levels before you commit serious money. Some people discover they prefer the next town over, or a condo instead of a house. We broke down the tradeoffs in renting vs. buying property in Costa Rica. Buying is easy to do later. Unbuying is not.

11. What will I do all day?

The beach is glorious for the first ninety days. Then it is just where you live. Retirees especially need a replacement for the structure work provided: volunteering, a sport, a business, a garden, a standing coffee group. The expats who thrive here have full calendars. The ones who struggle treat every day as vacation until the novelty wears off and boredom, or the bar, fills the space. Plan your Tuesdays, not just your sunsets.

12. What is my exit plan if it does not work?

Deciding what "not working" looks like before you leave is not pessimism, it is good planning. Set a review date, say 18 months in, and define what would send you home: money, health, homesickness, or a family change. Keep enough savings to move back without crisis. Knowing you have a way out makes the whole adventure feel lighter, and oddly, the people with exit plans seem to need them least.

13. Does everyone moving with me actually want this?

A move abroad built on one enthusiastic partner and one reluctant one is fragile. The reluctant partner's doubts do not disappear at customs; they compound with every hard day. Talk honestly about fears, deal-breakers, and what each of you needs to feel at home. If you have children, involve them early. Our post on what to know before moving to Costa Rica is a good conversation starter for the whole family.

So, should you move abroad?

If you worked through all 13 questions and your answers held up, you are ahead of most people who make this leap. The move itself is the easy part. If Costa Rica is on your short list, we are happy to share what daily life in Playas del Coco really looks like, no sales pitch required. Browse our current properties, or send us a message and ask us anything. We answer honestly, because we had to answer these same questions ourselves.

Frequently asked questions

How do I know if I should move abroad?

Test your reasons against reality. Spend at least a month living like a resident in your target town, build a line-by-line budget, confirm a legal path to residency, and price healthcare for your age. If the plan still works on paper and your family is on board, you are a strong candidate.

How long can I stay in Costa Rica as a tourist?

The US State Department notes that Costa Rican immigration authorities may allow visitors to stay up to 180 days without a visa, but the stay granted is not guaranteed and is set by the officer at entry. You also need a valid passport and proof of onward travel. Confirm current rules before flying.

Should I rent or buy when I first move abroad?

Rent first, ideally for six to twelve months. Renting lets you test neighborhoods, seasons, noise, and commute times before committing serious money. Many newcomers change towns or property types after their first year. Once you know exactly where you want to be, buying becomes a much safer decision.

Cover photo: Nataliya Vaitkevich, Pexels · Photo: Kristin Hardwick, CC0, via Wikimedia Commons