I retired in the No. 1 country Americans want to move to most—and I don’t regret it

In 2011, I walked away from a six-figure law career and retired at age 41. I thought I was financially ready. But emotionally? Not really.
After decades of working, I had become accustomed to the sense of purpose that a career brought, and I assumed that when I stopped working, I would have to give that up, too. My biggest fear took the form of great uncertainty: What would I do with all this unstructured time?
Fast forward 14 years later and my days are far from empty. My wife and I currently live in Portugal, the #1 country Americans want to move to. I spend my free time enjoying local food with my friends and walking along coastal paths lined with wildflowers. Retiring early is one of the best decisions I’ve ever made… but I remember how overwhelming it felt in the beginning.
Here’s what I’ve learned so far in early retirement and why I don’t regret it.
1. Uncertainty is an opportunity, not an obstacle
For most of my adult life, I followed a predictable path: law school, summer co-ops, and eventually a stable law career. Then came the 2008 financial crisis. The company I worked for collapsed, and my sense of direction collapsed with it. I couldn’t imagine doing anything other than practicing law.
I could have stayed in the industry. But instead I chose the unknown. Many people think that early retirement is about not working anymore. But it’s about redefining your identity without a road map. This required a change of mindset: I needed to become an explorer.
Ocean fog covers the Sintra forest within the Sintra-Cascais Natural Park near Lisbon, Portugal.
Alex Triassic
This mentality brought us to Portugal, a country where we didn’t speak the language, knew no one, and had no idea what to expect from day to day. It was confusing at first. But uncertainty has become our motivation to grow, learn, and build a fulfilling life from scratch.
If you’re postponing retirement because you don’t know what will happen next, that’s exactly why it might be worth doing. Uncertainty may be your opportunity to travel on roads you never imagined.
2. You can still get ahead financially even if you don’t have a paycheck
When we first retired, my wife and I assumed we would gradually reduce our savings over time and hope it would last. But something surprising happened: Our net worth continued to grow.
A big reason for this is that living in Portugal has greatly reduced our expenses. Here’s how much we save annually compared to our old life in Washington, DC:
- $15,000 in state income tax
- $25,000 for health insurance and deductibles
- $14,000 in property taxes
- $20,000 for meals, entertainment and daily expenses
In total, we estimate we’ll save about $5,000 a month just by living abroad.
We follow the same financial strategy we used when we were working: We live below our means, reinvest the difference, and let compounding do the work. The only difference is that we now earn income from investments instead of salaries.
Retirement doesn’t have to be the end of wealth creation. It might even be the beginning of a more sustainable, intentional version of this.
3. Finding purpose in retirement is just as important as finding it in your career
Whether you work or not, most of us want the same thing: to feel like we matter and that we’re contributing.
Shore incident crashed into rocks at Guincho beach, located on the Estoril coast of Portugal.
Alex Triassic
When we first retired, we had an established sense of purpose as parents of a young child. We attended school events, learned the local language and built a new life in Lisbon.
But when our daughter went to college, we were back to square one. Our schedules became empty and we faced the same question we faced in 2011: What will we do with all this time?
We made a plan before diving into hobbies or commitments. We have identified six key priorities that give meaning to our lives:
- Building and strengthening friendships
- Personal care and physical health
- Quality time as a couple
- Trip
- Volunteer work and giving back
- Learning new skills
Once you established these priorities, it became easier to create a satisfying routine.
Today, my wife volunteers at our tennis club, takes pottery and Dutch lessons, and does sports. I focused on writing, freelance retirement coaching, and helping a local nonprofit as a consultant. We host dinner parties, discover new recipes, and take short trips around Europe.
With the right mindset, early retirement can be the perfect new starting point. You just have to be willing to embrace it.
Alex Triassic He is a retired lawyer. He and his wife have been living in Portugal since 2015. He writes about tax planning, investing, early retirement, and expat life. bottom stack.
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