How I Was Building My Life Long Before I Moved To Spain
By the time we moved, the country almost felt like the least surprising part.
The typical narrative goes something like this: you wake up one day, decide you want a different life, and move abroad to find it.
For me, it couldn’t be more backwards.
Spain wasn’t the beginning of the story. It was the continuation of one that started when I was nineteen. I was only nineteen.
In the spring of 1995, I left my hometown in Western New York for South Florida and my first full-time job in radio, a goal I’d been working toward since before I was a teenager. I landed my first paying radio job in 1988—when I was thirteen—after spending years pestering everyone I could at a tiny AM station in Niagara Falls. A station that proved WKRP in Cincinnati to be true to real life.
The particulars aren’t especially important.
What matters is that when I drove south in 1995, I made a decision that would ultimately shape the rest of my life.
If you'd met me in 1995, you wouldn't have met some globally minded future immigrant. You would've met a twenty-year-old from Western New York who had barely seen the world and thought he already understood a lot more of it than he actually did. As much as I hate to admit it, if you’d shown that kid Donald Trump the politician, he likely would’ve supported him.
What mattered wasn't that I knew where I was going or who I’d end up being. I absolutely didn't. However, I had already become comfortable betting on uncertainty. I was willing to leave before I knew exactly what came next. That temperament—not Spain—turned out to be the constant.
I had already decided that I was willing to accept the tradeoffs that come with refusing to let geography—or one career, one city, or one version of life—define me.
Looking back, that decision mattered more than a destination ever could.
Everything that came afterward—San Francisco, 25 years total in California, academia, cycling, cities, journalism, bartending, eventually Spain—sprung from same willingness to keep moving toward whatever felt most alive, even when it meant leaving something else behind.
I think that’s a large part of why today—on the verge of 51—I’ve become so certain of how I want to spend my time and the people, places, and things I want to spend it with. I’ve come to the point where I can hold that list of people, places, and things in the palm of two hands.
When I left home—long before the age of reason—I had no clue that I’d fall in love with food, drink, cities, cycling, and all things urban planning. I already loved Bruce Springsteen, but had no idea I’d end up appreciating Tom Petty even more. I had no idea that I’d discover and add Elliott Smith, Social Distortion, Gaslight Anthem, and Old 97s to my favorites list. It never entered my imagination that, when I opened Spotify—yes, I still use Spotify—at age 50, I’d go for Spanish music because I like it and because it aids in the struggle of learning a second language.
All of this developed over time, but curiosity, movement, and reconstruction—for the most part—always remained constant.
A conservative kid from the northeast ends up in Miami not because he was dying to live in South Florida with the fruits and nuts, but because he has a radio career he was assembling. That’s part of a mindset that—if you have just a slice of open-mindedness somewhere in there—invites the evolution of curiosity, movement, and reconstruction that can change a human being.
Over time, I wasn’t merely curious about, moving for, or reconstructing my career—packin' and unpackin', town to town, up and down the dial—for radio. I was doing it because I started to discover that there was so much in the world I rejected as a teenager.
I developed a thirst for environments I had little experience with as a kid. Places I never imagined living, filled with people I never imagined living around.
All I know is that I’m lucky I became obsessed with radio at such a young age. It provided a way out of a place that—had I stayed—would’ve made it much more difficult to change. It would have stifled—if not rendered impossible—the ability to do what I did: continue to add and remove inaccurate and incomplete conceptions of the world from my view of it. You simply can’t go through this process unless you cast a net past the place you’re from and continue to widen that net throughout the years.
When you leave where you’re from and end up in a place that’s literally the complete opposite, you either go back home scared or keep casting a wider net. I witnessed more than one friend from my childhood take option one. But radio kept me out there—and the longer it did, the less staying away from home was about radio. It’s when pure curiosity, movement, and reconstruction took hold.
A concrete example: While in Boston to do my radio show from the 1999 Major League Baseball All-Star, I didn’t go to the game, even though my network provided a ticket and expected me to be there to mingle with sponsors. Professionally, I made the wrong decision, but in Boston I became obsessed with the city—with the city as an idea butting up against a place to live. So I spent as much time as I could wandering around it.
Long story short—that helped accelerate a move out of radio that was already in play. I was living in Las Vegas at the time for a temporary radio gig, mainly because I needed a job and wanted to work with a guy named Jay Clark.
With Boston fresh, life made it possible for me to move to San Francisco. At the time, people had called Boston the San Francisco of the West Coast. Turns out that that was a simplified version of reality, but it’s only an accumulation of experience that allows me to come to that conclusion today.
San Francisco continued the process of showing me what cities in the United States can be—and where they lack, particularly when compared to their European counterparts. So I enrolled in an urban studies program and became a student—really, an academic—for a solid eight years. During that time frame, I got into writing and riding my bike. Those experiences have persisted personally and professionally to this day.
So you can see the development I’m talking about here and how the progression of my life led me naturally to Spain. In many ways, Spain—or some variation of it—became inevitable. Because I knew enough about myself years after California became home—through accumulated experience, not to mention trial and error—to be certain about where I wanted to go, who I wanted to go with, and why.
At 25, everything interested me.
At 50, nothing and everything interests me.
That’s an important distinction. It’s just that somehow the combination of age and experience keeps you openminded enough to let new things in, but closed-minded enough to stop wasting your time and energy on—okay, cringe me and kill me for saying this—what doesn’t serve you.
But it’s true—as that person I love doing life with, my wife—likes to say!
Somewhere along the way, I also accepted something that people don’t like talking about when they romanticize moving abroad.
When you choose a place—when you choose a different path for your life—you do so at the expense of another. You loosen the relatively firm connection you once had with old routines, and, inevitably, some people. Distance redraws relationships no matter how much everyone involved wants to resist it.
This doesn’t mean you don’t hold onto the people you love. Of course, you do.
However, it’s a reality of life. If you want to grow and you want to see others grow (especially your kids), this process might be an inevitable ingredient in that growth.
That’s sad sometimes. It should be. But, to me, it’s also happy tears. Hanging onto the past often means you’re stuck in it. In that context, you—in concert with the other people around you—often bring or keep one another down. I’ve seen it play out so many times in my family and others.
This doesn’t mean tradition or choosing to do a life’s work go by the wayside. I’m only writing about my experience here, which fits with my personality. The key is truly finding a way to know who you are without letting where you are—when you’re in your teens, 20s, 30s, and 40s—completely define and destine you.
The losses you experience along the way equal the price of living the sort of life I’ve apparently been trying to build since I was nineteen.
Today, I know what a good Tuesday looks like—only because I’ve experienced so many different Tuesdays in my life. A few I’d like to forget. And more than a few that keep nostalgia alive, not as a way to ramble about how I miss things, but to ramble more productively about what I’m experiencing now.
I wake up next to my wife in a neighborhood we love. I write, ride my bike, and walk to the market. I’m slowly becoming a known entity in the neighborhood. I obsess over cities, public policy, food, music, and whatever idea has gotten stuck in my head that week. We plan the next trip—not because we’re searching for somewhere better, but because my wife and I remain curious about how other people have chosen to live, what other places look like, and how they feel.
None of that makes Spain perfect. It doesn’t erase the tradeoffs. It doesn't mean there aren't days when I wish I could teleport back to California to sit in the Frolic Room or see an Old 97s show with my kid.
It simply means I’ve finally reached a point where the life I live each day resembles the one I’d been unknowingly assembling for the last thirty years.
Looking back, that’s what all those moves were really about.
Not finding myself.
Just slowly building a life that made it easier to be the person I’d been becoming all along.
Track Residency Risk Before It Becomes a Problem
Flamingo Compliance helps expats, and remote professionals stay on top of tax residency, visa, and residency permit requirements across multiple countries and US states. The app automatically tracks travel activity and counts days against tax and immigration thresholds, alerting users as they approach a residency trigger or visa limit. When it’s time to file or report, detailed travel reports are ready to share with tax advisors or legal professionals.
Flamingo Compliance—Tax Residency & Visa Tracking
