My Greatest Risk

The Leap That (Almost) Made Me Vomit on an Airplane

There’s a moment – somewhere between the promise of potential and the utter dread of “what if” – that defines every leap of faith. For me, that moment took place in a cramped airplane seat on a flight to Berlin, clutching a lukewarm cup of herbal tea, trying to convince myself that I wasn’t about to dismantle my entire life over a crush.

Let me rewind.

You see, I’d always been someone who played it safe when it came to love. It wasn’t that I was unromantic (far from it – Yale taught me how to analyze every line of a Pablo Neruda poem until I cried), but I liked to have control. To plan. To know the ROI of my emotional investments. Love, though? It doesn’t work that way.

Which is probably why, when Anton – a multimedia artist with cheekbones so sharp they could’ve sliced through my careful logic – invited me to spend two weeks with him in Berlin, I froze. We had met during one of my consulting trips at a gallery opening in New York. He wore avant-garde streetwear and smelled faintly of bergamot. I was wearing a navy blazer, calculating which hors d’oeuvre tray to avoid so I wouldn’t stain my lapel. Two worlds, one orbit.

“It’ll be fun,” he said, smiling in that way that made me feel both amused and terrified. “Come see my Berlin. The city changes when the sun goes down.”

Reader, I am not impulsive. My closet is arranged by color and season. I categorize my books alphabetically, then by genre (with exceptions for anything signed or borrowed). But something about Anton – or maybe the way he made the world feel like it was teetering on a beautiful edge – inspired me to do the thing I never did. I booked the ticket.

Packing Regrets (and Emotional Baggage)

Cut to me, three weeks later, frantically Googling “how to look effortlessly cool in Berlin” from my Brooklyn apartment. If you’ve ever packed for a trip to impress someone, then you know the specific form of existential dread I’m describing. Do I own anything that says, “I’m cosmopolitan, but still relatable”? Spoiler: I did not.

If that wasn’t enough, there were deeper layers of doubt whispering under every fold of my suitcase. Was this trip an act of bravery or lunacy? Was I a romantic or a fool? Did my sudden fixation on German techno mean I was going through some kind of mid-thirties crisis? My parents (ever pragmatic) thought my decision was “ill-advised,” which is parental code for “you are absolutely losing it.”

But something inside me knew I had to do this. It wasn’t about Anton, per se; it was about me. About shaking up my comfortable, predictable life and leaning into uncertainty. The type of vulnerability I’d been too afraid to allow.

The City of Unanswered Questions

When I landed at Tegel Airport, jet-lagged but resolute, Anton greeted me with an enthusiastic hug and an itinerary that included rooftop parties, underground art shows, and lots of currywurst. From the moment we stepped into a neon-lit club pulsing with bass, Berlin unraveled itself as a kaleidoscope of chaos and creativity.

And while I’d planned to be bold and free, I quickly realized how unsteady leaps of faith can feel. I second-guessed myself constantly: Am I coming off too New York? Do I seem too eager? Did he notice when I mispronounced “Schönhauser Allee” at the subway station? Vulnerability started to taste less like champagne and more like choking on self-awareness.

But then, somewhere between a smoky record shop in Kreuzberg and a late-night café where he introduced me to something called Spaghettieis (yes, it’s ice cream shaped like spaghetti, and yes, it’s weirdly delightful), I had an epiphany. The moments that made me feel most out of my element – the ones tinged with minor embarrassment and raw sincerity – were the moments I was truly alive.

Anton didn’t seem fazed when I admitted I’d skipped techno night because I was too tired, or when I said I didn’t “get” some conceptual art piece he loved. Our connection transcended the façade I’d tried to maintain. The more I let go, the closer we became.

What Falling (Literally and Figuratively) Taught Me

Of course, not every leap lands the way you hope. Anton and I didn’t become a grand, earth-shattering love story. By week two, it was clear our wavelengths – though intensely gravitational – were also temporary. He was a nomad, and I craved roots. By the time I boarded the plane back to Brooklyn, we both understood that we weren’t each other’s final destination, just a meaningful stop along the way.

But here’s the amazing thing: I didn’t regret it. Not a single moment. Maybe that’s the real lesson about taking risks – they don’t have to be about “winning” or “losing.” Sometimes, just saying yes to possibility is the win.

Had I stayed in Brooklyn, I never would’ve danced on a warehouse rooftop with artists from three continents or eaten doner kebab at 3 a.m. below a glowing TV Tower. More importantly, I would’ve missed an opportunity to trust myself. To make choices not out of fear of failure but from a readiness to simply live fully.

Ready to Leap? Here’s What You Need to Know

If you’re standing on the edge of something uncertain – whether that’s a relationship, a move, or, heck, karaoke night – here are a few things I learned during my Berlin adventure:

  1. Don’t Wait Until You’re “Ready.” You’ll never have every answer, and that’s the point. Dive in when the water feels scary but exciting.

  2. Embrace the Awkwardness. Vulnerability is messy. It’s also the birthplace of great connections and even better stories (like “that time I got lost wandering Berlin and mistook a man in lederhosen for Anton”).

  3. It’s Okay if Things Don’t Last Forever. Not every risk leads to a happily-ever-after, but that doesn’t make it any less valuable. Find joy in the temporary magic.

  4. Bring Backup Snacks. This might not feel profound, but trust me: Berlin gave me some of my best memories – and the worst hunger-induced mood swings.

Conclusion: Leap Anyway

Do I still roll my eyes when people say “it’s about the journey, not the destination”? Sometimes. But now I understand why. Taking a risk doesn’t mean you’ll get it perfectly right – it means you’ll get off your couch and start living in technicolor.

So whether it’s saying yes to Berlin, introducing yourself to your subway crush, or booking the singing lessons you’ve always wanted (highly recommend), take the leap. Even when it feels terrifying. Especially when it feels terrifying. Trust me – the view is worth it.