I'm going to be honest about something: when we decided to move our family to Costa Rica, we weren't 100% sure it was the right call. We were maybe 80%. And some days, 60%.
That's normal. Anyone who tells you they were completely certain is either lying or didn't think about it hard enough.
How the decision started
It wasn't a lightning bolt. It was a slow realization that the life we were building, the one we were "supposed" to build, wasn't the life we actually wanted.
Good schools. Nice neighborhood. Solid careers. Two cars. A mortgage. We had the checklist covered. But something was off. We were optimizing for a future that didn't excite us.
Costa Rica started as a vacation conversation. "Wouldn't it be nice to..." Then it became a Google search. Then a spreadsheet. Then a serious conversation at the kitchen table after the kids went to bed.
What we did right
We gave ourselves a deadline. Not for the move. For the decision. We said, "In 90 days, we're going to have an answer: yes, no, or not yet." That constraint forced us to stop researching and start deciding.
We separated the financial question from the lifestyle question. I'm a financial planner, so naturally I wanted to model everything. But my wife rightly pointed out that we were using financial analysis as a way to avoid the scarier emotional questions, including what happens when one partner is more ready than the other. So we dealt with both, in parallel, not sequentially.
We talked to our kids. Age-appropriately, honestly. Not "we're moving!" but "we're thinking about something and we want you to be part of the conversation." Kids are more resilient than we give them credit for, but they need to feel included, not informed after the fact.
What surprised us
Healthcare was better than expected. We'd heard horror stories. The reality? Costa Rica's healthcare system is solid. Between CAJA (the public system) and private insurance, we've had excellent care. Is it different from the US? Yes. Is it worse? In many ways, it's better.
The cost of living is nuanced. It's not "cheap." It's different. Some things cost more (imported goods, certain electronics). Some things cost dramatically less (healthcare, fresh food, childcare). The net effect depends entirely on your lifestyle choices.
The expat community is both a blessing and a trap. Having English-speaking friends who understand your experience is invaluable. But if you only socialize within the expat bubble, you're living in Costa Rica without actually living in Costa Rica. Building a real social life takes intentional effort beyond the expat happy hours.
The hardest part wasn't the move. It was the three months after. The honeymoon phase ended right on schedule. Suddenly, everything that was "charming" was "frustrating." The pace of life. The bureaucracy. The Tico time. We pushed through it, and the other side was worth it. But those months were real.
What we wish we knew
Your financial advisor probably can't help you with this. Ours was great for US-based planning. Cross-border? Totally different skillset. We ended up having to figure out the tax implications, retirement account strategies, and estate planning gaps ourselves. That's literally why I built Vitality Wealth Planning, so other families don't have to.
You don't need to have everything figured out before you go. We tried. It's impossible. Some things you can only learn by being here. The key is having a solid framework and enough financial runway to handle surprises.
Your kids will adapt faster than you. Our oldest was speaking Spanish within six months. Making local friends within three. Meanwhile, my wife and I were still struggling with the subjunctive tense. Kids are incredible.
Would we do it again?
Without hesitation. But we'd do it with better financial planning (ironic, I know), more realistic expectations about the adjustment period, and less time trying to get permission from Google to make a life decision.
If you're considering a move, here's my honest advice: stop researching and start deciding. Take the Readiness Quiz, talk to your family, and if the answer is "maybe," let's talk. Sometimes a 30-minute conversation with someone who's been through it is worth more than 30 hours of Googling.