Thinking of retiring overseas? Read this first.

I was recently introduced to a couple now living in Morocco. Lovely people; thoughtful, curious, and wanting to get organized around their finances.

But I couldn’t take them on as clients.

Not because I didn’t want to, but because once you live outside the U.S., especially in retirement, things can get complicated fast.

It’s not just about citizenship. It’s about jurisdiction.

Some U.S. investment firms and advisors simply can’t legally serve clients who live abroad, depending on the country.

Even if you’re still a U.S. citizen.
Even if you want to keep working with the advisor you’ve known for years.
Even if the country seems financially “friendly.”

This couple had run into roadblocks trying to access or restructure their accounts. They were getting passed from person to person and didn’t feel like anyone fully understood what was going on.

I’ve seen this happen more than once, especially with legacy retirement plans that include annuity layers or insurance-based features. These structures can be hard to navigate. Even in the best of circumstances, they can be confusing, especially without industry knowledge. Trying to sort them out from overseas only adds to the challenge.

By the time they reached out to me, some of their flexibility was gone.

That’s just one piece of why it’s so important to plan ahead—well before retirement.

That’s when you want clarity. Not surprises.

Here are a few things to think through while you still have options:

🔷 Your withdrawal sequence — which accounts you tap first, second, and third, and how that timing shapes your tax bill over time.
🔷 Your long-term income design — how much comes from each source (IRAs, Roths, taxable accounts, Social Security) and how reliable or flexible you want that monthly income to feel.
🔷 Your advisor’s ability to keep working with you — whether your current firm can legally support you if you decide to live abroad, and what limitations might surface once you change residency.
🔷 Any structural changes to make before relocating — from simplifying accounts to updating beneficiaries or shifting investments that may not be available internationally.
🔷 The portability of your financial plan — how taxes, healthcare, reporting requirements, and local regulations might change your day-to-day financial life once you’re overseas.

If you’re even thinking about retiring overseas, bring it into the planning now.

You don’t want to be sorting it out from another time zone, with people you’ve never met, when the rules feel unclear.