Some decisions don’t just nudge you forward—they shove you into a whole other orbit. Maybe it’s taking that new job, moving to a new city, or saying yes to dinner with someone you’re not entirely sure about. I’ve always believed that life happens in the maybes—those blink-and-you’ll-miss-them fork-in-the-road moments where one answer changes everything.

The problem? You never know you’re in one of those moments until it’s already gone. And for years, one of those moments haunted me. It stuck around like the kind of ex who still casually likes your Instagram posts even though they very much should not. It’s the big what-if of my twenties: the career I didn’t chase.

The Call Sheet I Never Signed

Picture this: I’m twenty-four, fresh out of grad school, armed with two things—an MFA in Screenwriting and a dream list of studios I wanted to work for. You know the type: glossy offices where every meeting somehow includes both endless espresso shots and someone pitching a gritty reboot of Clueless.

And then came this curveball. A tiny production company—it didn’t even have its own dedicated lot—offered me a job. Small money, smaller team, but incredible creative control. They told me, “We want our scripts to sound like they’ve lived a life someone actually wants. Can we carve that out of you?” And oh, my ego loved it. But I also had an offer at a bigger studio, the kind with immaculate hallways and a name that made your aunt beam at family dinners.

One path was safe and shiny. One was a gamble bigger than Gollum’s final leap at the Ring. I chose the studio. The consistent paycheck lured me in like Netflix’s autoplay feature—“just one more” was impossible to resist.

Honestly, at first, it was glamorous, bustling, and fun in that Devil Wears Prada way. There were networking drinks on rooftops with a clear view of downtown L.A., and sure, I felt like I was living an Instagram-filtered chapter of my life. But deep down? I sometimes wondered if I’d bailed on the riskier path too soon. Did I shut a door I should’ve left open, just a crack?

Why Regret Shows Up Like a Bad Rom-Com

Here’s the thing they don’t tell you about regret: it doesn’t play fair. It doesn’t announce itself all at once. Instead, it’s that quiet voice during late-night reruns of your life’s weirdest decisions, wondering which alternate universe you might belong in.

For me, regret showed up whenever I heard about people who did pick the risky things. A friend-of-a-friend who landed a Sundance short. A college roommate whose tiny web series got picked up by Hulu. And then here's me: polishing someone else’s script into something their toddler nephew could technically read. Cut to me at 2 a.m., binging Mad Men and spiraling into questions like, did Peggy Olson ever take the easy way out? Probably not.

But then, something shifted. Regret became less of an unwelcome houseguest and more of a weird, overly honest mentor. I learned to sit with it. To listen. And here’s what I discovered: It’s okay to acknowledge that a road not taken wasn’t necessarily a missed opportunity—it was just one star in a constellation of decisions. Not every path floats your boat the first time. Some delays are blessings in disguise.

(Also, fun mid-revelation fact? Saying “constellation of decisions” earns major points at wine-and-cheese parties. Trust me.)

Do You Want a Red Carpet, or Just the Right Carpet?

Back then, when I chose the big studio, I chased the life I thought I should want. Familiar pressures nudged me toward the “right” choice. Beverly Hills doesn’t exactly raise you to believe in the beauty of small, messy beginnings. You’re meant to aim big—Oscars big, box-office-big, name-droppable-at-a-gala-with-Barbra-Streisand BIG.

But over time, I realized something more profound: Don’t chase what looks successful to others. Chase what feels fulfilling to YOU.

The little production company? Yeah, it folded within two years. If I’d taken that job, I might’ve been scrambling for rent and burning out on grocery-store sushi. Or, maybe I’d have written the script of my dreams. I’ll never know. But what I do know is this: the more time you spend mourning the what-ifs, the less time you give yourself to build the what’s-next.

Lessons for Your Own Roads (Because Trust Me, You’ve Got a Few)

Here’s what my regret-turned-life-coach taught me about navigating decisions—whether they’re career-related, relationship-driven, or just about picking a meal delivery service you don’t resent.

  1. Be Honest About What Pulls on Your Heartstrings.
    Is it safety? Thrill? Passion? Or just someone else’s expectations disguised as your own? No shame in the first or fourth, but try not to lie to yourself about what’s guiding you.

  2. Risks Are Sexy, But They’re Expensive.
    Big risks can feel tantalizing, but ask yourself: What’s my backup plan if this goes south? Having a safety net doesn’t make you a sellout—it makes you smart.

  3. Detours Aren’t Wasted Time.
    I used to think taking a “safe” road was a wasted opportunity. Now I see those years refining someone else’s scripts as my version of boot camp. I learned story structure like the back of my hand (and also learned to control FaceTiming my mom during work hours).

  4. Stay Inspired, Even If You’re Not Where You Thought You’d Be.
    When I finally started writing my own short-stories-turned-script-ideas, it was at 11 p.m., long after office hours. I didn’t realize it then, but creativity doesn’t need permission to find you. It just needs space.

What Happens Next

The road you didn’t take will tug at your sleeve every now and then. Trust me—every Shabbat dinner where my producer cousins casually slip in that they’re developing a streaming series about Jewish matchmaking (yep, that’s happening), the twinge of "what if" feels personal. But here’s my gift to myself, and to you: Forget the map. Focus on the next step.

You can make U-turns, switch lanes, even park for a while and reassess. The road isn’t constant; life’s more of a GPS that reroutes when you wander off-course. And sometimes? The view on the detour is better than whatever the shiny “best” path promised you.

Listen, I ended up here—writing this essay—and I couldn’t be happier to admit that I’m still figuring it all out. And maybe that's the lesson. Choose the best choice you can at the time, and trust that, even on the road not taken, you’ll find your way.

The beauty of life isn’t in taking the perfect path; it’s realizing that you’re still traveling.