Chasing Freedom: The Power of a One-Way Ticket

My first trip to Europe was a dream come true, and I can still remember the exact feeling when it finally came true. I had planned every step—getting a passport, storing my belongings, renting out my house, and clearing out the things I didn’t need in exchange for my freedom.

The choice I made wasn’t normal for most people, and my friends and family made that clear. Comments like “you’re insane,” “what the hell are you thinking?” and the classic “what are you running from?” were all thought-provoking—but not discouraging. If anything, they made my commitment stronger and my desire for freedom even more real.

I was at my mother’s house saying my final goodbyes and wrapping up a few last-minute details when she asked, “So, when are you coming back?” My plan to travel across Europe—starting in Ireland—had grown bigger than I expected. I decided it shouldn’t have a predetermined end. That would spoil everything it represented: freedom.

With a pause and a hesitant smile, I replied, “I don’t really know. I bought a one-way ticket.” Her jaw dropped, and a wave of worry spread across her face. I knew it wasn’t the right answer—but it was the right one for me. After a long talk, she reluctantly accepted my decision, though I could still see the doubt in her eyes, as if she were thinking, He didn’t really think this through. He’s having a midlife crisis. He’s running away from something.

But I wasn’t running away from anything—I was running toward something. Toward the life I’d imagined as a kid, watching movies about faraway places and reading books that showed only one picture of a world I wanted to see for myself. I was chasing the dream of travel, exploration, and self-discovery.

Yes, I was running—like a track star in a hundred-yard dash, full of energy and determination. It was exhilarating. I hadn’t felt that alive in years, and the excitement put a smile on my face that could have lit up a small city.

A Journey That Changed Everything

My one-way ticket turned into a year-long journey filled with adventure, joy, and transformation. The places I visited, the experiences I had, and the people I met changed me forever.

From the old Irish carpenter I worked with who smirked and told me, “Go home, Yank,” to the young German student who asked if I hated his people for what happened during the Holocaust—each encounter taught me something profound.

What I learned is simple: you have to go there to understand what it’s like to be from there. You have to listen—really listen—to what people are saying. When you do, you learn as much about yourself as you do about the world.

But after living in places for as little as a night and as long as a month, I began to feel drained and longed for home. I missed my family and my old life. Eventually, I purchased my one-way ticket back, happy to tell my mother—knowing it would make her smile.

That Christmas, as I sat at the dining room table sharing stories and laughter, I realized it had all been worth it: the missed trains, the uncomfortable beds, and the occasional inedible food. It was one great, unforgettable journey.

A New Beginning: Portugal and Beyond

Now, almost 24 years later, I’ve set out again—this time to retire and discover a new kind of freedom in Portugal.

Of course, the questions and remarks came flooding back: “What’s in Portugal?” my old boss asked. “I guess I’ll have to go and find out,” I replied. My brother laughed at my idea and said I was crazy. And yes, someone once again asked, “What are you running from?”

This time—at the end of 2025—I’ll admit I might be running a little. From the chaos in Washington, from rising costs and financial uncertainty, from the endless noise. But one question keeps echoing in my head: Why are you still doing this? You’re not getting any younger.

Is it a question of why? Maybe. I’ve asked myself that many times. My answer has always been: “Why not? What’s stopping you?” I’ve researched, prepared, and planned for every possibility. At this stage in life, it’s time to take another well-planned leap of faith and see what happens next.

Or is it a question of fear? As Franklin D. Roosevelt said, “The only thing we have to fear is fear itself.” I fear looking back ten years from now and realizing I spent a decade making someone else’s dream come true instead of living my own. I fear being too old to do the things still waiting on my bucket list.

Why You Should Take Your Own Leap

You might be thinking, I could never do that. And you’re right—if you think you can’t, you won’t. But nobody ever dies wishing they’d worked a few more hours or skipped another vacation.

The purpose of this post—and my entire blog for that matter—is to encourage you to explore, plan smartly, and embark on your own journey of discovery.

Trust me, if I can do it, anyone can. Take that well-planned leap of faith into the unknown. Start planning now and just do it—I promise you won't regret it.