The Road Not Taken
Life comes at you fast, doesn’t it? One minute you’re at happy hour, sipping on your third glass of wine (a terribly optimistic Chardonnay, if you must ask), and the next, you’re spiraling, wondering if that one decision ten years ago set off a chain reaction that led you to this very moment: swiping left on another guy in sunglasses holding a big fish.
This concept, the road not taken, has been haunting romantics and overthinkers alike since Robert Frost decided to make us all question every fork we’ve ever approached. And while his poem is beautiful, it doesn’t exactly clarify what you do when you’ve got two very attractive roads, both paved with temptation, and only one set of footprints in the sand (thanks, Frost and God).
As someone who has stood at a crossroads—emotionally, logistically, and yes, romantically—there’s something bittersweet about reflecting on the path I didn’t choose. So, today, we’re pulling up a chair, pouring a fresh coffee (or…you know, something stronger), and unpacking what to do when second-guessing creeps in.
Sliding Doors Moments
We’ve all had those pivotal moments when life feels like it’s straight out of a romantic drama. Maybe it was the decision to move to a new city, commit to a career, or end a relationship that no longer served you. For me, it was a decision that wasn’t so much dramatic as it was deceptively simple: stay in Washington, D.C., and continue a safe (but stifling) career in political speechwriting, or return to Texas for an MFA in creative writing—a choice as unpredictable as my hair on a humid Dallas day.
At the time, the “practical” voice in my head had a lot to say: “Ebony, you’ve worked to get here! Think of what you’ll sacrifice! D.C. brunches! Discount train rides to New York! Endless khaki-colored conversations about policy papers!” But then there was another voice, small yet persistent: “But what if…”
Fast-forward to now, and I’m writing from my sunny office in Dallas, sipping mint tea from a mug given to me by my messy-but-lovable writing group. Let me be clear: I love this life I’ve chosen. But sometimes, usually around 10 p.m. after watching a mindless rom-com like Something’s Gotta Give, I catch myself drifting. What if I had stayed in D.C.? Would life have unfolded differently—more predictably, more excitingly, more rom-com-ingly?
Regret vs. Reflection
Here’s the thing about wondering if you made the right choice: it feels like regret, but it’s usually just reflection wearing a dramatic hat. We all do it—revisiting old decisions, romanticizing discarded paths like they were flawless Instagram filters. But let’s get real: that path, as shiny as it looks now, came with baggage you’ve probably forgotten by now.
Your unchosen road, if we’re being honest, probably wasn’t all sunshine and butterflies. My alternate D.C. life? Sure, I see it now as a whirlwind of think tanks and tailored power blazers. But reality check: it also came with absurd deadlines, intense imposter syndrome, and way too many happy hours turned into sad hours (D.C. isn’t known for pushing boundaries on mixology).
A helpful tool when nostalgia hits? Remind yourself of what didn’t work. Did that old job drain your soul dry? Were you constantly battling a gnawing sense of discomfort? Were your non-negotiable needs in life (freedom, creativity, Tex-Mex) nowhere to be found? There’s power in remembering why you made your choice, even if the streets of your unchosen path always seem to smell like fresh lavender in your head.
Lessons From the Path You Did Choose
Here’s what reflection teaches you—it can bring clarity about what you’ve gained, even when you’re too stuck in the “what ifs” to notice right away.
When I look back on my decision to return to Texas for my MFA, romance was the last thing on my mind. But what I found along the way helped me grow into the version of myself sitting here, writing this. It wasn’t just about leather notebooks and dense creative workshops in small Austin cafes—it was about discovering parts of me I hadn’t even known existed.
I learned patience, a skill D.C. had practically wrung out of me after years of hyper-productivity. I found boundary-setting, too—a non-negotiable when you’re pursuing something as personal and vulnerable as your dreams. And yes, I discovered the art of saying no to stale relationships and shiny distractions that no longer aligned with where I was headed.
Are those discoveries the same ones I would’ve made had I stayed? Likely not. Each road—the one you walk and the one you don’t—has its own set of lessons waiting for you. Instead of mourning the lessons an unchosen path might’ve offered, take stock of the ones you’ve gathered by staying right where you are. Life’s biggest plot twists often come disguised as overdue self-realization.
How to Walk Your Path (Without Looking Over Your Shoulder)
So what do we do about this whole “grass is greener” syndrome? Here’s what works for me:
1. Write Your Own Narrative
The real reason some decisions haunt us isn’t that we made the wrong ones but because we keep forgetting we’re still in charge of the story. Start framing the path you’re on as the one you’re meant to take. (Think of it like re-writing your rom-com, except one where you actually like the ending.)
2. Find the Gold in Your Current Road
Regret thrives when you focus on what you lack. Instead, try jotting down what your current path—this exact version of life—has brought you. Maybe it’s independence, a village of friends, or toes-down certainty that you love what you do, even when it’s hard.
3. Stop Romanticizing Alternate Realities
Remember Gwyneth Paltrow in Sliding Doors? Both of her timelines were messy and chaotic and beautiful in their own ways. So why do we act like our “other” road would’ve been pure perfection? Next time you feel your thoughts drifting off down Fantasy Lane, lovingly remind yourself that every decision comes with trade-offs. Those trails lined with roses? Yeah, they probably also had thorns.
4. Focus On the Road Ahead
Lean in to the endless possibilities that still lie ahead. There’s always room to make new choices. In fact, some of the best roads aren’t the obvious ones; sometimes they’re the trails you blaze yourself.
The Takeaway
Looking back can be bittersweet, yes, but it can also be a reminder of just how far we’ve come. True, you didn’t walk every road, but the one you did take led you here—to all the people you’ve loved, lessons you’ve absorbed, and memories you’ve built.
So here’s my advice: stop staring into your rearview mirror and start looking forward. Because whether you chose the “safe” path or the one drenched in risk, you chose you. And when all is said and done, what better road could there possibly be?
