There’s a Japanese proverb I grew up hearing: “Fortune favors the bold.” It’s the kind of thing your parents say while watching you hesitate over a big decision—like whether to try out for the track team or confess feelings to your classroom crush. At the time, it was little more than background noise in my childhood. But years later, it echoed in my head when I found myself standing at a bar in Vancouver, realizing I was about to take the greatest risk of my adult life.

As someone who thrives on the comfort of predictable routines and the safety of measured decisions, my leap of faith felt as foreign as skydiving without a parachute. But sometimes, life has a way of nudging you… or, in my case, gently shoving you. And that push? It involved a one-way flight, a cryptic postcard, and a tiny vase of flowers.

The Leap: From Tokyo to Vancouver

This story begins a few years back when I was still working as a curator at a modern art museum in Tokyo. For those unfamiliar with the profession, museum curation is a well-ordered world where precision reigns supreme. Budgets, timelines, and inventories ruled my days, and the only surprises came from accidentally finding a half-eaten onigiri someone had hidden behind a priceless sculpture (true story). My life was predictable down to the second—and I liked it that way.

But then came the email.

It wasn’t from a gallery or an artist I’d been chasing for months. It was from him. Let’s call him Dan—partly because that’s his name, and partly because it captures his unassuming, easygoing nature. Dan and I met during my research stay in Vancouver years ago. He worked part-time at a used bookstore where I’d go to lose myself for hours. Like a scene straight out of a Nora Ephron movie, he’d recommend novels while stacking paperbacks, and somehow, our connection grew between the pages of Haruki Murakami novels and well-worn travel guides.

When my research term ended, I returned to Tokyo, leaving Dan to his coffee-stained counter and second-hand books. We still wrote postcards—yes, the analog kind—but I never thought those little snapshots of our long-distance friendship would lead to anything more. That is, until I got his email.

“Rina,” it said, “I’m putting together a show for local artists here and was wondering if you’d help with curating. Stay with me if you’re up for it!”

At first, I brushed it off. A side project in Vancouver? I was managing one of the busiest seasons at the museum—plus, I hadn’t left Japan in years. I couldn’t just up and leave. Right? But as I stared at his message, I considered something terrifying: What if I stayed afraid of shaking things up?

The Reality of Risk: When Overthinking Meets Opportunity

Saying yes was harder than I’d like to admit. Leaving Japan for an uncertain opportunity felt reckless and strange. Would Dan and I still click after years apart? Would I even enjoy curating something on my own, without the resources of a major museum? But beyond those questions lay the bigger fear: disappointment. Because let's be honest—sometimes risks don’t reward you with fireworks and fanfare. Sometimes they just fizzle out quietly.

But I went. Armed with one suitcase, a few hardback journals, and an irrational amount of green tea, I stepped into Vancouver’s drizzly spring and showed up at Dan’s doorstep. And while I didn’t know it at the time, the biggest transformation wasn’t about the project, or my career—it was about letting myself be vulnerable.

The Outcome: What We Find When We Leap

Helping organize the art show was everything I didn’t know I needed. The work was messy, chaotic, and miles outside my comfort zone. I was used to pristine glass cases and polished exhibits; here, I was stapling flyers to lampposts and sorting through abstract pottery that resembled something my five-year-old niece might’ve cooked up in her art class.

And yet, for all the unpredictability, it was exhilarating—and grounding. Breakneck deadlines left no time for overthinking. Curating alongside local artists and volunteers reminded me that it’s okay if things are imperfect; what mattered was connection. Somewhere along the way, Dan and I fell into an easy rhythm, rediscovering the humor and ease of our bookstore days. We weren’t quite strangers but weren’t familiar either—that heady space where attraction blooms.

The show eventually came together, and while it didn’t attract massive crowds or critical acclaim, it felt like a triumph in my eyes. More importantly, it gave me a powerful sense of freedom. I wasn’t just living life by the rulebook anymore—I was co-writing it with every risk I took.

And Dan? He and I went for sushi to celebrate opening night. It wasn’t a grand confession over candlelight. It wasn’t backed by swelling orchestral scores like a Ryuichi Sakamoto soundtrack. It was just simple. Honest. Unfolding exactly as it should. While our story didn’t involve dramatic fireworks, our connection deepened in ways I never saw coming.

Lessons in Letting Go

What I love most about art—and life, for that matter—is its refusal to be boxed in. The same applies to love. It doesn’t arrive predictably with a perfectly written timeline. It grows in the unknown and thrives on risk. Taking that leap wasn’t just about career growth or a new city. It was about stepping away from my curated comfort zone and toward something far messier, but far more meaningful.

For those hesitating on the edge of a decision, here’s what I’d say:

  • Start Small: You don’t need to cross continents to take a risk. The tiniest steps—striking up a conversation, saying yes to dinner, or sending a thoughtful email—can lead to the biggest shifts.
  • Ditch Perfection: Too often, we shy away because we think things need to go flawlessly. Spoiler alert: Nobody gets it perfect, and that’s what makes life interesting.
  • Embrace Uncertainty: Life doesn’t always give guarantees. Sometimes, the miles traveled matter more than the destination.

The Takeaway: You Are the Greatest Risk and Reward

Looking back, I often wonder how different my life would be had I stayed in Tokyo, wondering “what if.” Taking that leap helped me rediscover not only my work but also myself—my ability to adapt, connect, and embrace the unknown. The boldest choices often feel scariest, but maybe that’s their power. Fortune, after all, favors the brave.

Whether it’s accepting an invitation, moving across borders, or trusting in an imperfect opportunity, remember: you are your greatest investment. So, take the chance. It’s messy and beautiful, just like love itself.