I once read a quote that said, “The biggest risk is not taking one.” Which sounds great and all, but try remembering that when you’re standing at the edge of something uncomfortably uncertain—like, oh, hypothetically, selling everything you own to follow a man across the country after exactly three months of dating. Spoiler: that man ended up being a blip, but the risk? That changed my life.

Let me take you back to the summer of chaos, otherwise known as my twenty-fourth year on this wild spinning planet. I had just wrapped up a fellowship in Taos, my heart living its best artsy, high-desert dream. My days were spent writing ingenious (read: probably cringey) short stories. Someone at the retreat had referred to me as “a modern-day Georgia O’Keeffe,” and I let that nickname go straight to my head. But then, like all good fellowship programs, the funding dried up, and I found myself back in Santa Fe, artist brain intact, wallet… not so much.

Cue Ethan.

We met at one of those downtown gallery walks that everyone pretends to enjoy but mostly attends for free wine served in plastic cups. He wore a hat that I should have hated—like something from an indie band's live album cover—but on him, it just worked. Within three weeks, he knew how I took my coffee, what made me belly laugh, and how to pull me out of my very serious “artistic existential crises” (i.e., when my laptop battery died). Within three months, he had a job offer in Chicago, and I had one terrifying question: “What’s next?”

The Leap Before the Net

Here’s the secret about risk-taking no one tells you until it’s too late: it doesn’t come with a pro/con list. There’s no guaranteed safety net, and when I said, “What if I just went with him?” my friends tilted their heads like confused puppies. My mom actually dropped a bowl of red chile (which is, frankly, sacrilege).

“Lila,” she said, in that stern but somehow still loving tone perfected by mothers with daughters prone to impulsive romances, “this is not one of your stories. If it goes wrong, you can’t rewrite the ending.”

Still, there was this whisper inside me, insistent and untamed, that said playing it safe wasn’t my style. So after much internal (and external) debate, I packed a single suitcase, kissed Santa Fe’s golden light goodbye, and hopped on a plane with Ethan.

Windy City, Wild Heart

I don’t want to paint too stark a picture, so I’ll summarize: Chicago proved colder than I could fathom (physically and emotionally), Ethan and I unraveled faster than cheap yarn in a high-speed wind tunnel, and I found myself alone in a studio apartment the size of my parents’ closet. One day, I looked out the window at a pile of dirty, gray snow and thought, “So THIS is what risk tastes like.” Spoiler again: it’s bitter, with notes of regret.

But funny thing about survival—you find your legs, even on ice. I threw myself into writing, fueled by heartbreak and caffeine from too many late-night diner shifts. I stumbled into a community of aspiring writers and visual artists who knew what it meant to build from scratch. We were all struggling, we were all half broke, and we were all gloriously, recklessly alive. For the first time, my work felt… real. It had teeth.

Ethan faded to a fond(ish) memory, but Chicago? That city broke me open and gave me back something better in return: courage.

Lessons from the Leap

Looking back, it wasn’t leaving Santa Fe or chasing love that was the real risk. It was betting on myself, even when every logical piece of advice said not to. I’ll never forget the feeling of designing my first solo exhibition back home years later, surrounded by people who believed in my work—and in me—because I’d finally done the same.

Could you take a risk as big (and mildly impractical) as stuffing your life into a suitcase for someone who may or may not be your soulmate? Maybe. Should you? That’s your story to write. But here’s what I learned about making a leap, whether it’s for love, art, or anything else that sets your heart racing:

  • Gut Check Before the Go: You don’t need certainty, but you do need clarity about what YOU want. Is it for someone else—or for yourself? There’s a difference, trust me.
  • Acceptance is Key: Not every risk pays off in the way you imagine. Sometimes doors slam shut, but often, windows crack open. (With Chicago’s weather, it was more like a drafty overhead vent, but hey, anything counts.)
  • Find the Why: It’s not about where you land—it’s about why you jumped in the first place. If you can embrace that, even faceplants will come with grace.
  • Let It Shape You: Every leap, crash, and climb back up reveals something about yourself. In taking a chance, I learned resilience, adaptability, and most unexpectedly, joy.

Closing the Chapter

So, was it worth it? A thousand times yes. Not because it was free of pain, but because it put me in motion and taught me to trust the unpredictability of life.

The thing about taking risks in love—or anything, really—is that you’re opening a door without knowing where it leads. Sometimes, you step into a vibrant new reality. Other times, it’s just a hallway leading you back to yourself. Either way, you’re better for the walk.