There’s a moment in every good Western when the hero stands on the edge of a cliff, metaphorically—or sometimes literally—staring down a life-altering decision. Maybe it’s whether to ride into the frontier, guns blazing, or to settle into the quiet life of ranching back in town. For me, that cliff moment wasn’t a showdown with bandits or a cattle stampede. It involved a backpack, a one-way ticket, and a crush who didn’t even know I liked her.

The Crush That Spurred It All

Let me set the scene. It was late spring in Colorado, that bittersweet time of year when the snow finally melts, and the landscape is so green it looks like it’s been Photoshopped. I had just finished grad school in Virginia and returned to Telluride to figure out what was next. My plan? Well, I didn’t have one. My parents suggested working a summer back at the ranch, guiding kids who’d never seen a horse outside an Instagram post. My brain said, “Sure, that’s safe.” My heart? It had other ideas.

Her name was Lily. She was from Denver, and although we’d known each other since high school, we’d somehow reconnected on a visit home. Over coffee one day, she told me she was planning a month-long trek on the Camino de Santiago in Spain. “I wish I had someone to go with,” she said. Now, I should clarify—at this point, we weren’t dating. Heck, we weren’t even in that ambiguous talking stage that modern dating thrives on. But something about her smile mixed with the way she said she was nervous about going alone lit a fire under me.

The old me would have ignored it. But not this time. I blurted out the words before I could stop myself: “I’ll go.”

What followed was a slightly stunned silence, followed by her raising an eyebrow and saying, “Really? You’d just drop everything to hike 500 miles with me?”

Without thinking, I replied, “Why not?”

The Leap Before the Net

Once the initial adrenaline or maybe sheer lunacy wore off, reality hit. Taking a leap of faith sounds poetic in theory—like something you’d find in a Hallmark card or a Nicholas Sparks novel. The truth? It feels less like courage and more like panic when you’re in the thick of it. I wasn’t just signing up for a scenic hike with someone who made my heart race. I was signing up for uncertainty, discomfort, and quite possibly rejection.

The prep was, in a word, chaotic. I didn’t own a decent pair of hiking shoes, let alone any clue about what “trekking poles” actually did. My Spanish vocabulary was limited to ordering burritos, and I’d never traveled internationally by myself before. Add to that: My parents thought I’d lost my mind, and my friends alternated between “This is the most romantic thing ever,” and “You’re definitely going to die.”

But something within me—call it gut instinct or just old-fashioned stupidity—told me to push ahead. I booked my ticket. Then, armed with nothing but an overstuffed backpack and a vague promise from Lily to “meet me at the starting line,” I boarded the plane.

Finding Your Footing—Literally and Figuratively

The Camino itself was… humbling. Day one, I got blisters the size of quarters within the first six miles. Day two, we got lost trying to decipher a map (the markers were literally giant yellow arrows—don’t ask me how we messed that up). By day five, I had learned to apply duct tape to my feet like some kind of avant-garde protest against bad footwear.

But more surprising than the physical hardships were the emotional surprises. Sharing close quarters and hours of walking each day quickly peels back the layers of politeness and small talk. There were moments Lily and I bickered over silly things—where to stop for lunch, or whether I was walking too fast (or, as she exaggerated, “leaving her in the dust like a poor Western sidekick”). But there were also moments of quiet connection—sitting side by side at a stunning overlook, sharing trail mix, or laughing at how miserably sunburned we both were.

As much as I wanted this trip to be about getting closer to Lily, it became something else entirely. Somewhere in the middle of those long miles, I turned inward and started examining myself. The truth I’d been avoiding back home became clear: I had been scared to take risks my whole life. Sure, I’d moved east for grad school, but I’d clung so hard to what was comfortable, never venturing too far from the career path or the familiar. The Camino was teaching me, step by step, to let go of control—and to be okay with not knowing the outcome in advance.

The Risk That Paid Off (Even If Not How I Expected)

So, what happened with Lily? Well, here’s the part where life throws you a curveball. By the time we finished the Camino, we knew each other a lot better—a little too well, in fact. Somewhere along the way, I realized she wasn’t the person I’d built up in my head, and she realized the same about me. Our friendship deepened, but romance? It quietly fizzled out like the campfires we’d shared in the albergue courtyards.

You know what, though? That was okay. Instead of feeling embarrassed for chasing a crush halfway across the world, I felt weirdly proud. I’d done something bold and stupid and terrifying—and I’d come out the other side with stories, perspective, and a deeper sense of my own resilience.

The Camino taught me that taking a leap isn’t about the outcome—it’s about the attempt. The risk itself is the reward. Maybe you get the girl (or guy, or whoever); maybe you don’t. Maybe the journey leads you somewhere entirely unexpected. The point is, you’ll never know until you take the first step.

Lessons Learned (And Why You Should Take Your Own Leap)

If you’re standing at your own metaphorical cliff, wondering if you should take a chance—on a relationship, a career, or even just stepping out your front door—here’s what I learned along the Camino:

  • Trust Your Instincts. Your heart knows when it’s time to leap, even if your brain is screaming, “Nope.” Listen to that little nudge.
  • Plan, But Don’t Over-Plan. I had no clue what I was doing on that hike, and it worked out fine. Sometimes, the best adventures come when you stop trying to control every detail.
  • Find Joy in the Moment. Whether it’s a breathtaking sunrise or a silly inside joke, savor the small moments. They’re what make the leap worthwhile.
  • Embrace Uncertainty. The whole point of taking a risk is stepping into the unknown. Accept it, learn from it, and let it surprise you.

A Final Word on Courage

Life, like a good Western, isn’t about playing it safe. Whether you’re hiking across Spain for love, starting a new relationship, or just braving the vulnerability of opening your heart, the magic happens when you take a risk.

The real “greatest risk” is staying on the sidelines, wondering what might have been. So, saddle up, take the leap, and see where the trail leads. Who knows? You might just discover something far greater than what you set out to find.