We’ve all been there—standing on the edge of a decision, heart racing, weighing two paths like some ancient philosopher, only to realize you didn’t have the faintest idea what you were doing. For me, that crossroads came in the form of a relationship, an almost-love that will forever dwell in the annals of “what if.”

I often think about how our lives hinge on moments so mundane they slip by unnoticed—like when I met Jack (not his real name, but let’s spare him the Googling). It was just another farmers’ market Saturday in Bozeman, the air crisp with a bite of October and the faint scent of cider mingling with hay.

He wasn’t remarkable in the classic rom-com way—he wasn’t brooding in a bookstore or chasing after my train in the rain. He was selling artisanal goat cheese and handed me a sample. The look that passed between us wasn’t love at first sight—it was more like, “Hey, I believe in the superiority of snacking on local cheese, too.”

Jack was all high-country charm, with hands calloused in a way that spoke of hard work and stories I’d never get tired of hearing. He texted me once to say, “I repaired a fence, and a coyote watched me the whole time, like a tiny foreman.” What was I supposed to do with that kind of information? Fall a little bit in love, obviously.

But things weren’t simple. They rarely are when two people with vastly different ideas of life bump into each other. He made it clear early on that, just like his notoriously stubborn goats, he wasn’t leaving his land outside of Livingston. For someone who used to parade around her childhood ranch dreaming of New York publishers and faraway cities, that was a hard no.

And so I stood there, at the figurative fork in the road that Robert Frost made sound so poetic and not at all gut-wrenching.

Two Roads: The Pull of Possibility

Here’s the thing no one tells you about these major life decisions: neither path comes with a neon-lit sign that says “Guaranteed to Make You Happy.” I knew if I stayed and chose Jack, I’d likely swap some of my life’s ambitions for the rhythm of communal dinners, baby goats, and an endless view of Montana sunsets. Sounds dreamy, right?

But dreams often have fine print, and mine came with the realization that tethering myself to that world would also mean untethering myself from the very independence and ambition that have shaped me.

You see, in Montana, folks romanticize cowboys and poets, but the life itself isn’t romantic. It’s raw, unfiltered work. Some days, it’s poetry; most days, it’s broken fences and frozen pipes. And while part of me longed for that intimacy—the knowing glance Jack would throw me across a dinner table stacked with bread bowls and candles—I also wondered if I’d resent him one day for pulling me from my writing, my stories, my people.

Reflections From the Trail I Took

I said goodbye to Jack on an unassuming Tuesday morning, somewhere between coffee and the perpetually melancholy aroma of packing tape. Our breakroom goodbye wasn’t grandiose; it was full of polite smiles that both of us pretended not to notice shaking. He watched me drive away in my rust-red Subaru, not knowing he'd feature prominently in the mental reels I’d replay on sleepless nights.

What happened next? Life, mostly. I doubled down on my writing career, took trips to promote my book, fell for someone new (a city-loving historian who I’d later discover hated dogs—an unforgivable oversight on both our parts).

But here’s the thing about the path you didn’t take: it never fully vanishes. Every so often, I imagine Jack still out by that fence line with his coyote foreman, squinting at the horizon in a way that made you think he could see things you couldn’t. I’ll wonder if he ever married, if he names his goats after obnoxious politicians to spite them (this was a running joke we loved).

And sometimes, when the city crushes me with its noise and sour coffee, I picture myself there beside him, wearing muck boots and cradling a newborn kid goat while the wind smells of sage and pine.

Lessons for Fellow Travelers

If life is a trail, every step—whichever direction—is both a risk and a reward. Here’s what my foray into “The Road Not Taken” taught me:

  • You Can’t Have It All (and That’s OK): Forget Instagram platitudes about balance. Choosing one thing inevitably means unchoosing another. There’s no “perfect” choice; there’s only the best one for you in that moment.

  • Let Yourself Mourn the Path You Didn’t Walk: Even the right decision comes with loss. You’re allowed to think about the guy who got away or the leap you didn’t take. Just don’t unpack your emotional U-Haul in that space forever.

  • Carry What’s Worth Carrying: Every relationship—whether it thrives or ends—leaves its fingerprints on your soul. Jack taught me to romanticize cozy mornings, to pause for the wind through the trees, to laugh at myself more often. It’s okay to take those lessons with me, like a postcard from a road you’ll never drive again.

Finding Home in Your Choice

Looking back now, I don’t regret the road I took, although I’ll always wonder about the other one. Maybe that’s what Frost was trying to tell us—that no matter what path we choose, it’ll carry some kind of beauty and breaking. You find peace not by questioning the road but by walking it wholeheartedly, embracing both the wildflowers and the blisters.

And as for Jack? Who knows? Maybe one day I’ll stop by that farmers’ market again and find him there, still selling cheese and coaxing smiles out of strangers. Maybe I’ll thank him for reminding me what it feels like to stand at the edge of possibility with your heart wide open. Or maybe, just maybe, I’ll take the cheese and keep walking.