The Wishbone of Choices: Reflecting on the Road Not Taken

Life, as I’ve learned, has a peculiar way of cornering you into choices that feel too big to fit in your hands. You stand there, holding a wishbone of a decision, staring down twin paths like a traveler in a Frost poem. To take Choice A is to wade into uncharted waters; to choose Choice B is to cling to the safety of solid ground. The thing is, no matter which way you go, there’ll always be a little gravel under your boots that wonders what the other road felt like.

For me, the biggest fork in the road came years ago—not on some windswept mountain trail or deep in the throes of winter by a crackling ranch fireplace—but smack in the middle of a city café during a quiet moment that could’ve been plucked straight from a Hallmark movie.

She asked me to leave Wyoming.

And here’s the thing: I almost did.

That Time I Almost Ditched the Cowboy Boots

We’d been together for three years, surviving off the kind of low-budget romance that thrives on shared playlists, hand-me-down paperbacks, and badly made pancakes on slow Sunday mornings. She was a city girl through and through, with ambitions that reached sky-high and a sense of direction so sharp it could have been GPS-enabled. And I was… well, me—a guy who found his north star somewhere between the ridgelines and the campfires.

She wanted to move to San Francisco. I didn’t.

But it wasn’t as simple—or as stubborn—as that. I thought about going. Really, I did. She teased me with the promise of lattes that didn’t taste vaguely like campfire ash and a warmer climate where snow boots wouldn’t see the light of day. She whispered about art galleries and bustling farmers’ markets where everyone seemed to have a dog or a yoga mat.

For her, it was both a dream and a dare. For me, it was the start of an inward wrestling match.

Wyoming was my roots, but she was my heart. Which one do you pick when they seem to stand at odds?

Romantic Ruts and Pick-Up Trucks

They say hindsight’s 20/20, but I’d argue it’s more like 50/50—half clarity, half cringe. Looking back, we were playing tug-of-war with each other’s dreams, hoping neither of us would let go of the rope. She felt I was stubborn, clinging to my identity like a cowboy holding onto a stubborn bronco (her words, not mine). I felt she was asking me to leave everything that made me “me” behind, like some romantic version of trading a saddle for a swivel chair.

Spoiler alert: Ultimately, I didn’t go.

We broke up on the back porch of my family’s ranch house, with the Grand Tetons in the distance, eavesdropping on the kind of words that tighten your throat. She left two weeks later; I stayed.

In my more melodramatic moments, I like to think of that porch scene as akin to a spaghetti Western standoff but with a lot more tears and a lot less Clint Eastwood. In reality, it was just two people who loved each other deeply but couldn’t seem to reconcile their wildly different visions of the future.

And yet, even with that chapter long closed, there’s a part of me that occasionally wonders: What if?

Trail Markers on the Path Not Taken

A funny thing about decisions: They’re rarely as black-and-white as they first feel. At the time, choosing to stay in Wyoming felt like staying true to myself—but what if I’d left? Would I have thrived in San Francisco, embracing city life with open arms and finally learning the difference between capers and whatever else they put on artisanal toast? Would I have found new ways to fall in love, both with her and with a world that spoke in skyscrapers instead of sagebrush?

Sometimes the “what-ifs” sneak up on you in moments you least expect. They nudge at you while you’re chopping firewood, or catch you off guard when you see an Instagram ad for an overpriced urban loft.

Yet, while the curiosity lingers, I’ve also learned the importance of embracing the imperfections of the road I did take. Here’s the thing about choices: Whichever path you follow becomes the one you pave, day by day.

For me, that’s meant building a life that continues to honor who I am—and who I was back then. It’s meant writing, guiding others through the wilderness, and finding comfort in the rhythm of places that feel as constant as they are unpredictable.

It’s also meant making space for new connections and new dreams, ones that fit me like a well-worn Stetson rather than trying to squeeze into someone else’s hat.

Lessons from the Road You Choose

Let’s face it—you’re never going to fully silence the voice that wonders what life might have been like if you’d taken the other road. But you can learn to live alongside it, like an old friend you share coffee with once in a while. Here’s what the wishbone of decision-making has taught me:

  • You’re Allowed to Make “Selfish” Choices: And by “selfish,” I really mean honest. Relationships often require compromise, but if compromise becomes a coat you can’t shrug off, it might mean you’re losing too much of yourself in trying to make it fit.

  • Love Doesn’t Eliminate the Tough Choices: Movies sell us the idea that love conquers all, but in reality, love often asks for tough conversations and harder boundaries. It doesn’t mean it wasn't real—just that life is complex.

  • Dreams Don’t Always Overlap, and That’s Okay: It’s not a reflection of failure if two people can’t align their goals seamlessly. Sometimes the kindest, most loving thing you can do is let go, painful though it may be.

  • The What-Ifs Make You Human: Choosing a path doesn’t mean you can’t glance over your shoulder every now and then. Just don’t let the rearview mirror overshadow the view ahead.

Living Loud on the Way Forward

I often tell people that life is like climbing a rugged trail in the backcountry. Sometimes you can’t see what’s around the next bend, and sometimes you pick a route that turns out steeper than you expected. But if you stop, even for a moment, and take in the view around you, you realize it’s pretty incredible—imperfections and all.

For me, choosing to stay in Wyoming wasn’t just a decision to honor where I came from. It was also a choice to embrace the unknowns of what staying would look like. It meant risking heartbreak and loneliness, but also reconnecting with a self I might have lost if I’d traded the mountains for the Bay Area.

The road not taken will always be there, gleaming faintly in your memory. But so will the one you’re walking now, with its own secret beauty and hidden blessings. There’s no map for life, but if you’re lucky, you might just find you’ve been exactly where you needed to be all along.