Today marks my fourth anniversary… with Rome.

Of course, it’s been an up-and-down relationship. And will it be “till death do us part”? Too early to say. But, like any epic romance, Rome has changed my life—and changed me—in ways that, just a short time ago, seemed highly unlikely.

And so I’m incredibly thankful that, four years ago, a younger version of myself faced up to some serious questions. Am I happy doing what I’m doing? What might make me happier? And, most crucially, What might I regret not doing?

They are the same questions that, at some point, we all have to face. And the answers I got back were, as they are for so many people, incredibly intimidating. If not downright scary.

In my case, I kept coming back to one thing. I wanted to quit my job as a magazine reporter to become a freelance writer… in the midst of a recession, and without much financial cushioning. And to move from Washington, D.C. to Rome, Italy… where I didn’t speak the language, didn’t know anyone, and wasn’t sure, yet, how I’d wrangle a legit legal status.

It hadn’t always been that way. I’d enjoyed, at the beginning of my job, the “real world” rituals of donning a pencil skirt and lipstick at 8am, of commuting to the office alongside other young professionals in suits, of clicking through the halls of Congress with a reporter’s notebook in hand—and, yes, of receiving a steady, if paltry, paycheck, access to a HMO, and a few new lines to put in my résumé. I felt productive, efficient, and capable.

I also felt empty.

After a few months, it became clear that I wasn’t where I was meant to be. Maybe not ever. But for right now. Because, for right now, my office was papered with postcards of farflung places. The bookshelves in my apartment sagged under the weight of travel memoirs. And all I could think about was how I’d pursue a life of travel and writing.

My specific idea bubbled up as a pipe dream I’d think about while waiting for a source to call me back, or between press conferences, or while willing the queue of other young professionals at Trader Joe’s, also pushing carts filled with fat-free Fage yogurt and organic granola and roasted garlic hummus, to please move just a little bit faster.

I wanted to move to Rome: a city I’d visited only a few times, but (predictably, given my love of history and art) fallen in love with. And try freelance writing.

It was just a fantasy. At first. But the more I thought about the move, and reached out to expats living in Rome, and spoke to freelance journalists and travel editors, and researched my legal options for living there, and, most of all, asked myself what I reallyreallyreally wanted from my life, or at least my life in my 20s, the more freaked-out I got.

Which might have made someone saner else decide that thank you, but no thank you, this wasn’t the move for them.

But I knew I was getting freaked out because I was approaching a decision of yes. And for someone who’s really sorta kinda Type A, who likes having a nice clean picture of what her future is going to look like… well, saying yes to something that felt like jumping into the abyss? That’s just about the scariest thing you can do. No wonder I was freaked out.

When I was agonizing over the move researching my options, I reached out to an editor who had lived in Rome for years. “I just don’t know what to expect if I do this,” I told him.

“Well, there’s no way to know,” he said, matter-of-factly. “You’ll never know unless you come here. But remember: Da cosa nasce cosa. One thing leads to another.”

At that moment, I knew I might regret the move. I might have to return to the States after just a few weeks, shame-faced, begging for a job. Or for a roof over my head. But, when I was old and gray, I thought I’d regret my humiliation less than I would regret not having gone at all.

So I went.

And? It hasn’t been easy. I’ve had horrible, no-good, very bad days. I’ve missed friends and family. I’ve had moments of hating living in a different culture, especially one that can be as potentially infuriating challenging as Italy.

But, in my wildest (day)dreams, I’d dreamed that, at some point, I’d be able to balance a life of writing and photography with one of travel and exploration. That I’d write for publications like National Geographic Traveler and the New York Times and Travel + Leisure, maybe even for a guidebook or two. That I’d have the freedom and flexibility to take on projects that enthralled me, to go to art museums in the middle of the day, to take impromptu trips abroad.

That I’d have a website, or be on television, or any of the other great things that have come my way, because I put myself in this position, didn’t even occur to me then. Nor, of course, could I have predicted how many wonderful people who would wind up crossing paths, and lives, with me in Rome. Or how many adventures I’d have, from battling Umbria’s backwoods in a 4×4 truck to ducking oranges in Ivrea’s Battaglia degli Aranci.

After all: Da cosa nasce cosa. 

The big lesson I’ve learned by moving to Italy? The need to treat life—with its expectations, and pressures, and commutes and cubicles and pencil skirts—a little less seriously. And treat my own life—innermost dreams, goals, the things I don’t want to regret years down the road—a whole lot more seriously.

Well, that… and to never drink a cappuccino after noon.