Moving Abroad – The Best Adventure Yet!
- itllbefunretiremen
- Mar 14
- 5 min read
Updated: Apr 30
We talk about it all the time. Sometimes we think people are tired of hearing us go on and on. Then, we meet someone new—someone just starting out on their own adventure—and suddenly, we’re right back at the beginning, reliving the excitement all over again.
The emotions of moving abroad are vast and varied, but no matter where we come from, we all share so many of the same feelings.
Retirement Was Looming—But We Weren’t Ready
For us, it started with a simple truth: we were getting older, and retirement was looming. But we hadn't quite cracked the code on becoming financially independent. We were still working on the financially independent part when we realized—wait a minute—we also needed to figure out how to slow down and actually live the retirement lifestyle we dreamed about.
The big question: How could we take what we had, maybe build on it, and turn it into an adventure?
So we searched. For years. Looking for that perfect place where we could rub a couple of nickels together and still live a dream life.
And now? Well, as I write this, I’m sitting on my balcony, overlooking the ocean and the quaint little town we now call home on the island of Madeira.
Yes, I’m still working—building a small company to help others create the adventure they crave. Because the truth is, some of us have only a small pension, Social Security, or a little investment nest egg. Others have gobs of money.
But guess what we all have in common?
We want something more.
We need courage.
And we all wish we had more time for this adventure we’re creating.
We’re also looking for like-minded people to connect with.
The Big Questions Everyone Faces
It doesn’t matter where we’re moving to or how we’re going about it—Latin America, Europe, wherever—we still face the same big questions:
What visa do we need?
Should we learn a new language?
Will we fit in?
Can we afford it?
What don’t we even know to ask yet?
For us, it was about adventure. We wanted one more big adventure before we got too old to do it.
And, to be honest, we were selfish—we didn’t just want this for ourselves. We wanted something different for our youngest son, too.
We didn’t want him stuck in the cycle of working 5-6 days a week, living for that one two-week vacation, then counting down the days until the next one. We didn’t want him skipping pro football games or Broadway plays because even a weekend trip cost a fortune.
So, we brought him with us.
It took some convincing, but… we won.
At First, It Was Just a Crazy Idea
When we first talked about moving abroad, it wasn’t about adventure—it was about survival.
We simply couldn't afford to retire comfortably in the U.S. without ending up in a broken-down trailer under a bridge by a murky river.
When I first brought it up, Alan just looked at me like I was crazy and walked out onto the porch. But over the next few weeks, then months, we both caught the bug.
And when one of us started to doubt it was possible, the other one believed enough to keep us moving forward.
We talked to people all over the world. We asked questions. We listened to their stories—what worked, what didn’t. We read books. Bought programs. Joined online groups.
You name it, we did it.
And little by little, it started to work.
At first, we weren’t even thinking about Southern Europe as an actual, affordable possibility. But eventually, we saw the light.
And let me tell you—we are so glad we did!
Every single day, we wake up feeling amazed, grateful, excited.
What the Doubters Said You Can't Move Abroad
Of course, when we first told our friends and family, most of them gave us that look—the one that says, Yeah, right. That’ll never happen.
Some even asked, Why would you leave the U.S.?
Well, here’s why.
We had watched my parents sell everything they owned, pay cash for a house in Florida, and settle into what they hoped would be their forever home. But even with a paid-off house, their small nest egg and Social Security weren’t enough. Medical expenses and unexpected costs drained everything.
Eventually, they had to sell again.
They moved to a trailer park. Hoped they could live on Social Security alone.
They couldn’t.
So, they moved in with family.
That was it. The end of their adventure.
But at least they got a few years of their dream before it slipped away.
We wanted our dream to last.
So, we knew Florida—the retirement destination for Midwesterners—was not for us.
Our Biggest Champion Was the Most Unexpected Person
Guess who cheered us on the most?
Leslie’s bedridden mother.
She was the one who pushed us to figure out how to create a side income we could take with us. She learned right along with us from her bed in Kentucky as we discovered how to invest for ourselves.
She was there when we finally realized that—while our financial advisor was a nice guy—he wasn’t the be-all, end-all.
We could do this.
We learned to analyze companies.We learned to be patient and buy at the right time.We learned to use options for short-term income.
We may have been late to the game, but buddy, we did not miss it!
And now, Wolf has become quite the financial manager himself.
What a team we make!
The Takeaway—You Can Do This Too!
Okay, maybe this article didn’t turn out exactly the way I first imagined.
But here’s what I really want you to know:
🌍 You can build an amazing adventure—somewhere in the world—despite your fears, despite your limitations.
We’ve been living in Portugal for over three years now.
Yes, it took us ten years to put it all together.
But we did not miss our chance.
And every year, it just keeps getting better.
We’ve met the most incredible people—some have become lifelong friends, while others have moved on, expanding their own adventures.
We’ve already done more than we ever thought possible.
We’ve traveled all over Europe, grown our businesses, and created a life we could never have planned.
So, what are you waiting for?
Come join us.
It’ll Be Fun.
Connect with us via:
Comments