In light of recent federal mandates to return to the office, Pedro is having a hard time giving up on his fully remote lifestyle. Is there a creative solution to his dilemma?

An anonymous caller is excited to move abroad permanently. How should she structure her investments to support her international lifestyle while maintaining a home base in the US?

Former financial planner Joe Saul-Sehy and I tackle these questions in today’s episode.

Enjoy!

P.S. Got a question? Leave it here.

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Pedro asks (at 01:55 minutes): How can I find a fully remote job as a computer programmer so I can return to a location-independent lifestyle with my family? I’m a federal employee and I’ve been called back to the office. But it feels like I’m losing something deeply important.

During the pandemic, my job went fully remote, and I spent a year traveling the country in an RV with my partner and two kids. We visited 35 national parks and it was the most meaningful experience of my life. That time reshaped how I view my priorities, family life, and future goals.

I homeschool my kids, and I want them to stay connected—to each other, to us, and to the world around them. We’re all on board with a nomadic lifestyle, and eventually, we’d love to travel overseas again.

The challenge is that I’m struggling to find a fully remote job. I’m a computer programmer with more than a decade of experience, so the work can be done remotely. I’ve been applying and submitting resumes, but beyond that, I’m not sure what to do.

I’ve read that while interest in remote work is high, many companies are reversing course and bringing people back to the office. So what’s the best strategy to break into a truly remote role right now? Do you have any advice, especially from your own freelancing and travel journey?

Anonymous asks (at 24:54 minutes):    What’s the best way to invest a $500,000 windfall if I’m planning to leave the U.S. and live abroad full-time?

I just sold my primary residence, which I owned outright, and I’ll be walking away with half a million dollars. I also have $50,000 in a taxable brokerage account, and I receive $1,400 a month in Social Security Disability Insurance (SSDI).

I can’t work due to an autoimmune disease that flares up unpredictably—but interestingly, when I’m outside the U.S., I seldom have flare-ups. My doctors think it might be environmental. So I’m leaning fully into this lifestyle change.

I’ve sold everything I own except for one small storage unit. I’ve lived all over—Europe, South America, Asia—and I speak four languages, so I’m very comfortable abroad. I live simply, well below my means, and I prioritize experiences and creativity over material things.

Eventually, I’d like to establish residency in another country. I know I’ll need to show proof of income for that, so I’m considering dividend-paying ETFs or stocks as a way to generate passive income. I also have a virtual U.S. address and plan to keep my citizenship.

So, with all that in mind: How should I invest this money to support a long-term, low-cost, international lifestyle? Are there any specific considerations I should be aware of—either because I’m on SSDI or because I’ll be managing my investments while living overseas?

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