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The traditional path of working until 65 isn’t for everyone.
Many talented people are stuck in the grind, thinking they need multi-millions before making their dream of living abroad a reality. But here’s the truth: semi-retirement abroad isn’t just for the ultra-wealthy. It’s for anyone willing to think differently about work, life, and money.
Key Takeaways
- Start by spending 3-6 months in your target country to ensure it’s the right fit for your semi-retirement lifestyle.
- Connect with local entrepreneurs and expat groups before moving to avoid loneliness and ease your transition abroad.
- Research countries that offer favorable tax benefits and flexible visa programs for expats.
- Create flexible income sources through freelancing, consulting, or online businesses that can travel with you.
What I’m Telling My Clients
Semi-retirement means stepping back from the 9-5 while still earning income on your terms—through part-time work, consulting, or passion projects. The goal is to cover essential expenses with semi-retirement income while letting your retirement savings grow. Here are seven tips I’m giving my clients who are interested in semi-retiring abroad:
1. Test Your Destination First
Want to know the fastest way to torpedo your semi-retirement dreams? Jumping in without testing the waters first. Those Instagram photos of digital nomads working from beach cafes in Bali? They don’t show the whole picture.
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Start with a 3-6 month stay in your target destination. Countries like Portugal, Spain, and Malaysia offer extended tourist visas perfect for this purpose.
2. Build Your Support Network
Here’s something most financial advisors won’t tell you: the biggest challenge isn’t managing your money—it’s building your community. Loneliness is real, even in paradise.
Start building your network before you move. Join online expat groups and connect with local entrepreneurs. If you find your tribe early, you’ll have friends waiting when you arrive.
3. Select a Tax-Friendly Country
The right location can save you thousands in taxes each year. However, it’s important to be smart about it.
Countries like Portugal, Malaysia, and Costa Rica offer attractive tax benefits for semi-retired expats. Plus, their flexible visa programs mean you can still earn income without jumping through endless bureaucratic hoops.
4. Create Flexible Income Sources
Semi-retirement doesn’t mean zero income—it means income on your terms.
Set up a portable work system that travels with you: a reliable laptop, cloud storage, and a list of global co-working spaces. Whether you’re consulting, freelancing, or running an online business, your income should be as mobile as you are.
5. Secure International Health Coverage
Nothing kills the dream faster than a medical emergency without proper coverage.
Invest in an international health insurance plan that covers both your new country and the U.S. While it’s an extra expense, it’s also your ticket to peace of mind (and potentially lower healthcare costs overall).
6. Manage Your U.S.-Based Assets
This is an area where things get interesting (and where many people mess up). Your U.S.-based assets don’t disappear when you move abroad—but the rules for managing them change.
Understand how your retirement accounts, investments, and real estate will be taxed in both countries. It’s important not to try and DIY this part.
7. Partner with a Cross-Border CPA
Think of a cross-border CPA as a financial translator. They’ll help you navigate the complex world of international tax treaties, foreign-earned income exclusions, and compliance requirements.
The Bottom Line
Remember: Building your semi-retired life abroad is like building a house—brick by brick, with a solid foundation first. Focus on getting these seven elements right, and you’ll be amazed at how achievable your dream lifestyle becomes.
