The Road Not Taken
Growing up in Boulder, CO, my weekends were a kaleidoscope of earthy textures: soft pine needles under hiking boots, the smell of wood smoke drifting up from forest clearings, and the sound of my dad debating politics with other activists over bowls of vegetarian chili. My parents believed life was a series of deliberate choices—about what you stood for, what you consumed, and how you showed up for the world.
Naturally, this ethos bled into my decision-making process. At 18, when others were simply picking college majors like they were items on a diner menu, I was agonizing over the repercussions of studying Environmental Policy instead of English, wondering which path would allow me to "make the greatest impact" (and also worrying if leaving out commas in journal entries made me a hypocrite).
But the irony of The Road Not Taken scratches deeper when I think about Amy. Yes, we’ll call her Amy—not because I’m avoiding messy pseudonyms, but because every aspiring romantic decision-maker needs an Amy to contend with.
Crossroads in the Rockies
Amy and I met during our senior year of high school in an overscheduled microcosm of teen stress: a biology field trip at Rocky Mountain National Park. People always romanticize “field trips” like they’re hotbeds of covert romance, but let me assure you nothing feels less sexy than being knee-deep in mud with a clipboard of amphibian population data.
Yet, there was Amy. She wore muddy boots and spoke like a naturalist fluent in some secret language. Instead of dreading the ten-page report we’d have to turn in, she talked about how climate change would quietly unravel everything we took for granted. Not exactly flirty—but incredibly magnetic.
Over the next year, we became inseparable. Let me clarify: inseparable in that sweet-but-also-torturous phase where you’re teetering on the edge of defining a relationship. We liked the same indie bands, spent hours looking at constellations in Eldorado Canyon, and shared a borderline-obsessive attachment to chai tea lattes from our neighborhood cafe. And yet, when graduation loomed, so did the fork in the road.
Amy got into a university in California and was set to study ecological restoration. I’d chosen to stay local at CU Boulder. She wanted us to “try and make it work,” but in my typical overthinking style, I kept flipping back to the idea of paths diverging.
The Road I Didn’t Take
Here’s the brutal truth about being cerebral in relationships: you get a very romantic-sounding excuse to ruin everything. The mechanics of overdoing it were simple. I told myself long-distance relationships were distractions, that Amy deserved someone as unflappably ambitious as she was, and that maybe our paths weren’t meant to run parallel forever. Basically, I wrapped emotional cowardice in ambition and self-sacrificing rhetoric.
We said goodbye on one of those final June evenings where the sky looks impossibly lavender. I masked my guilt under stoic determination as she wiped silent tears and kissed me goodbye. We both said things like, “This is what’s best for us,” which is the worst kind of lie—it’s the kind you believe.
The funny thing about decision-making, though, is that it never really ends when you take one road over the other. Later that summer, I started hearing songs that reminded me of her in the strangest places—played over speakers in discount gear stores, on the radio of a coworker’s busted Subaru, even hummed unconsciously by strangers. Her shadow stretched into college, as I sat through ecology lectures wondering if she’d have laughed at my professor’s dry humor or deconstructed it. Did we break up because it was practical—or because I was afraid to choose?
Reflection Is a Two-Way Mirror
Let me pause this emotional spelunking to make something clear: I don’t regret who I’ve become. The path I chose—conservation work, creative writing, a fiercely loyal pack of friends who’ve stayed up late debating precisely how much butter makes the perfect pancake—helped shape me in authentic, wonderful ways. But looking back, I do wonder if my hesitance to try with Amy wasn’t misguided.
Why? Because her absence taught me something monumental: no decision feels perfect, because no life path is devoid of risk. There’s always a twist or setback waiting down the road. Staying in Boulder didn’t magically make me immune to heartbreak or restless longing; it just gave me different things to wrestle with. The choice we make doesn’t insulate us from regret—it only teaches us which regrets to live with. And that’s not always a bad thing.
Why Timing Isn’t Always to Blame
Hindsight has a cheeky way of letting you zoom out, showing you how all the factors aligned. In Amy’s case, “timing” partially played a role—but it’s such an easy scapegoat, isn’t it? Timing gets blamed when we’re too scared to dive headfirst, when we hit emotional speed bumps we don’t feel like navigating, or when we’re just not paying attention to the opportunity standing in front of us. Timing is an excuse we slap onto the really thorny truths.
Here’s the big, unvarnished insight I wish someone had told me back then: Risk is underrated. Seriously. Sure, if you go all-in on a relationship, you might crash and burn. But if you never open that door, you’ll never feel the indescribable swell of connection, either—the kind that makes national park constellations feel like a chapel and chai lattes taste like memories in a cup.
Lessons From the Road Taken
So, what can we learn from this mildly awkward love story? If life is a series of forked paths, here are three takeaways from my own:
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Stop Playing Nostradamus
You don’t rank relationships through predictive analytics. Calculating whether someone’s “worth it” is impossible when feelings are involved. Feelings are messy. Welcome to life. -
Let Yourself Be Scared
Fear doesn’t mean you’re doing something wrong—it usually means you’re approaching something meaningful. Deciding out of fear to avoid vulnerability might feel safe at first, but in the long run, it’s lonely. -
Understand That Love Evolves
Who you love, how you love, the timing—it all shifts over the years. The person you’re madly enamored with now might fit a different puzzle piece later. That doesn’t diminish what they meant in the moment.
A Winding Path Forward
Years later, I bumped into Amy again at—of all places—a sustainability conference. She was helping spearhead efforts to restore a watershed in the Sierras. I was there to cover the speakers as a budding writer. We grabbed coffee, laughed like old friends, and talked about our hometown with the kind of reverent nostalgia you only get from having left it. Was there a spark? Sure. But it wasn’t one I needed to rekindle. We’d grown. Evolved. Persisted in our respective directions.
The road not taken isn’t failure; it’s a reminder of the infinite alternate routes any of us could have traveled. And in reflecting on those unchosen avenues, you might just stumble across an entirely new perspective—if not love itself.
Because no matter which road you walk down, the secret to finding connection—both with others and with yourself—lies not in the path but the willingness to keep walking. Let those boots get muddy. The destination, I promise, isn’t what you think it is.
