“You’re going to regret this,” my best friend Luke said, visibly uncomfortable as I packed the last of my clothes into an already-bursting suitcase. I’d heard him say those words before—usually when I was ordering mystery meat at a street food stall or contemplating a vintage jacket that looked better in theory than on my frame. But this time, we weren’t talking about culinary gambles or regrettable fashion choices. This time, the stakes were higher. I was moving to London.

For context: I’m not impulsive. I’m the guy who reads every Yelp review before booking a restaurant. When I buy airfare, I double-check the dates like I’m defusing a bomb. My motto has always been: "Prepare for the worst, laugh when it doesn’t happen." But last year, something shifted. Call it a quarter-life crisis or the magnetic pull of British pubs; either way, the opportunity to work briefly at a travel magazine came up, and I leapt at it. No safety net, no blueprint. Just me, a suitcase, and a Google Doc ominously titled "London Survival Plan."

Here’s what I learned from that leap, and why I’d do it all again—regardless of how terrifying it was.

Why Staying Safe Feels So Good (But Gets You Nowhere)

I’ll admit it: Toronto had become my comfort zone. I had routines, favorite cafes where the baristas knew my oat milk order, and a reliably tepid dating life that felt more like swiping for mild amusement than true connection. The city, as dynamic and buzzing as it was, had started feeling like a beautiful sweater that didn’t quite fit anymore.

But comfort is sly. It’s warm and easy, wrapping itself around you until you can’t tell if it's protecting you or suffocating you. I realized this when I was catching up with an old friend and we could sum up my past year in two lines:

Friend: “So, what’s new with you?”
Me: “Not much. Same job, same neighborhood, same everything.”

Two nights later, the London job opportunity landed in my inbox like a late-night drunk text from the universe. It said: Time to take a chance. And this time, for once, I said yes. I wasn’t entirely sure what I was saying yes to, but rejecting it felt worse than risking failure.

Let’s Talk About Fear—and Why It’s a Jerk

Moving to a different country when you’re a chronic over-thinker is, to put it bluntly, like climbing into a hamster ball filled with bees. Every anxiety buzzes louder than the last. What if I don’t meet anyone? What if I hate the job? What if my flatmates are cult members and not the quirky-but-lovable British types with Union Jack teapots?

Those were my more (somewhat) rational fears. But fear also whispers ridiculous things in your ear. Things like: “Don’t go. You’ll miss out on the new season of The Crown.” Classic fear tactic—make the mundane seem vital and the unknown too great to risk. The truth is, fear doesn’t vanish when you take a leap of faith. It follows you to a new city, sits in the passenger seat when you’re on a double-decker bus, and asks if you’re sure you can handle what’s ahead. But fear also shrinks the moment you push past it, the way shadows disappear when the sun finally comes out.

Learning (and Failing) in London

Here’s a scene for you: Two weeks into my London adventure, a coworker invited me out to what they casually called a “pub quiz night.” I heard “trivia,” feared nothing, and waltzed in ready to prove that my random knowledge of ‘90s sitcoms and hockey stats would earn me instant team captain status. I was, however, not prepared for the British intensity. These weren’t just quiz enthusiasts. They were seasoned gladiators armed with obscure facts about 14th-century monarchs and cricket.

We finished in dead last. Now, in Toronto, I’d probably laugh it off and slink home—but something about being in a new city urges you to double down. I opened up to my coworkers after our loss, joking about my utter failure to contribute more than, “Uh, Benedict Cumberbatch?” when asked for an answer in the music round. That little moment? It broke the ice. By the end of the night, we weren’t just coworkers—we were becoming friends.

Every new leap goes like that. Sometimes you crush it (hello, finding the perfect local cafe near my flat that serves scones as if they’re manna from heaven). Sometimes you stumble (like when I accidentally said “cheers” to a barista instead of “thank you,” and they stared at me like I’d just proposed marriage). But failure, it turns out, has a way of making you stronger. And funnier. And, oddly enough, braver.

What Risk Taught Me About Relationships

You might wonder what all this moving and pub-quiz-losing has to do with dating and relationships, and I’d argue: everything. When you uproot your life for something new, it forces you to meet yourself in ways you never quite did before. It’s like any good relationship—sometimes thrilling, sometimes awkward, always revealing.

In dating, we often play it safe. We stick to familiar date spots, recycle the same compliments, and nervously laugh at jokes we don’t wholly find funny, because the idea of being fully ourselves feels too risky. But isn't it? The best connections—whether romantic or platonic—happen when we cannonball into vulnerability. London, with its crowded Tube rides and impossibly sludgy weather, taught me to let people in quicker. To embrace silences instead of filling them with chatter. To risk being bolder with what I want. (Yes, there was a brief but endearingly disastrous flirtation that culminated in me mispronouncing "scone" in front of someone I was trying to impress—but I digress.)

What Taking a Risk Actually Rewards You With

By the time I left London six months later, I was forever changed. Not necessarily in obvious ways—you wouldn’t look at me and think, “Dan’s gone full British.” But I held myself differently. I smiled more, laughed more loudly, and said “yes” to opportunities before analyzing them to death. Risks don’t always pay off in explosive, fairy-tale ways. Sometimes the reward is subtler: a strengthened sense of self, new perspectives, and a deeper appreciation for the courage it takes to jump.

Would I recommend uprooting yourself on a whim? Probably not on a whim. But I will say this: If something scares you just enough to make you curious—say yes. Life isn’t meant to be wrapped in bubble wrap. It’s meant to rattle you. And if the rattling knocks things loose, chances are, it’s clearing space for better things to grow.

So go ahead. Take your leap. Who knows what’s on the other side? Maybe a terrible quiz night. Maybe the love of your life. Or maybe, just maybe, a better you.