“Do I turn left or pull a full-on Eat, Pray, Love detour?" That was the question playing on repeat in late 2017, when the fork in my personal “life road” materialized faster than a rom-com montage. I was 28, living in a cozy East Austin bungalow, and trying to decide if I should take a stable nonprofit job half a mile from my house or accept a wild, dream-like offer to move to San Francisco and join an experimental arts collective. (Think: lots of oversized installations, vegan potlucks, and the lingering risk of running into your most pretentious ex.)

I picked stability. I stayed in Austin, kept my nonprofit gig, and wrote essays on the side, sipping coffee that didn’t cost $6 per cup. But sometimes, on quiet mornings or during certain waves of existential FOMO (yes, that’s a thing), I wonder: What would life have looked like if I’d gone?

And while this reflection might feel like a tribute to Robert Frost’s most memed poem, it’s more than that. The road not taken isn’t some philosophical shrug. It’s a way to reflect on our values, desires, and, oddly enough, our relationships—especially with ourselves.

The Sliding Doors of Love and Life Decisions

Life, like those nineties Gwyneth Paltrow movies, runs on micro-decisions. You say yes to one thing, and you’re saying no to another. You ghost a perfectly “nice” human on a dating app (can you ever trust someone who only says, “How’s your day?”), and then two weeks later, realize nice doesn’t sound so bad. You book the Austin-to-Denver flight instead of the Austin-Denver hiking trip and spend the weekend charmed—yet slightly annoyed—by your cousin’s new rescue cat.

When it came to my own choice between comfort and chaos in 2017, I asked a million people for advice, because, obviously, the world needed more opinions. Turns out, everyone was split 50/50. My dad, ever Team Stability, reminded me how “rooting yourself can lead to better growth.” My artist friend Marsha nearly booked my ticket to the Bay, declaring, “Austin will always be here. Go throw a paint balloon at capitalism!”

In the end, I pulled a Rory Gilmore and overanalyzed my way into staying. At the time, it felt like self-care masquerading as logic. But deep down, I knew: choosing Austin wasn’t just about career moves. It was about self-preservation in the face of change that felt like too much, too soon. Sometimes, the road not taken isn’t a missed opportunity; it’s a message from our intuition to slow. the. heck. down.

The Grass Isn't That Greener

Fast-forward a few years, and I’ve heard tales of what could’ve been. Turns out, most of my potential San Francisco roommates moved back to Kansas and Michigan because even artists deserve more than 400 square feet and dry ramen for dinner. Not exactly the utopia I’d imagined.

Meanwhile, staying in Austin let me deepen ties with this city in unexpected ways. I carved out weekly art classes at a co-op downtown, began mentoring students who’d never held a brush before, and cultivated a sense of community that space-dust buddha bowls in California couldn’t replace.

The thing we forget about roads not taken is they’re rarely perfect. Sure, the flashy path is tempting, but much like that Instagram couple whose every outing looks like a boho-chic fairy tale, the reality behind the screen is usually way messier.

Whether it’s a career leap or relationship choice, every road comes with potholes, long stretches of concrete, and the occasional highway breakdown where you ask, “How the hell did I end up here?” Grass looks greener because it’s Instagram-filtered, y’all.

Choosing Ourselves Vs. Choosing the Unknown

Okay, let’s get a little real: This isn’t about roads; it’s about choices—and what those choices say about who we are at the time.

When I think back to my 2017 self, I realize she wasn’t ready for constant reinvention in a city like San Francisco. At the same time, she was ready to redefine “adventure.” It didn’t have to mean crossing state lines. Sometimes, it’s about crossing thresholds you’ve built around yourself, discovering where you’re stuck, and who you want to be outside of slickly marketed dreams.

Too often, we carry this shame about “what could’ve been”—the relationship that didn’t last, the job we didn’t risk, the brunch we skipped because we were just so tired. Newsflash: choosing what feels right doesn’t equal failure. Yes, there’s value in embracing mystery and change—but there’s also honor in stability, in nourishing what you already have.

Five (Unsolicited) Lessons I’ve Learned from Roads Not Taken

I know what you’re thinking—serious Whitney wisdom vibes—but indulge me. Here’s what reflection taught me when I dropped the what-if weight:

  1. Regret Doesn’t Have to Be Your Frenemy. Just because you didn’t pick Door #2 doesn’t mean your life behind Door #1 lacks meaning. Sometimes we’re exactly where we need to bloom.

  2. Choices Aren’t Darling Little Boxes. They’re more like Duolingo lessons. Pick one language and commit, but hey—if you wake up tomorrow longing to learn Finnish instead of French, life’s still got options.

  3. Trust That You’re Not Stuck. Yes, anyone who tells you “time heals everything” is kind of annoying (and often wrong), but pathways unfold in directions we can’t yet predict. Be open to curves.

  4. FOMO Is a Liar With a Megaphone. That influencer in Bali probably cried over a delayed flight and soggy tacos before their perfect sunset selfie. You missed nothing, babe.

  5. Anchor to Your Core Desires. What did your decision reveal about you? For me, staying in Austin was saying yes to connection, creativity, and really good tacos.

Conclusion: Your Two Roads Are Yours Alone

Here’s the thing: Every single one of us will face a thousand “road not taken” moments, both small and life-altering. Choose your way. Own it. Let life surprise you.

I still wonder about San Francisco sometimes—about whether I’d have grown into one of those effortlessly cool, kombucha-brewing artist types. And then I glance out my window at East Austin: the neighbor walking his pug, kids painting murals on a cracked brick wall, and a sky that somehow looks Texas-big even in fall.

This isn’t the road not taken. This is the road I crafted. And for now? It feels just right.