I once heard someone compare making a major life decision to jumping off a cliff and building your wings on the way down. While that sounds poetic, it’s also wildly impractical—like trying to assemble Ikea furniture mid-freefall. Risk is scary, and it should be. But sometimes, taking a leap of faith isn’t about soaring. It’s about trusting that the ground beneath you knows how to catch you.

My greatest risk wasn’t a movie-worthy “all or nothing” moment. There was no slow-motion leap, no adrenaline-pumping soundtrack. Instead, it was a deliberate step into something wildly uncomfortable: leaving my carefully set life in Montgomery and venturing into the intimidating unknown of the rural Deep South to collect oral histories from people I didn’t know and who didn’t immediately trust me.

This is a love story, but not the kind you might think.

The Perfectly Good Life I Left Behind

Picture this: I had a stable job at a local museum—charming, steady, with regular hours and a desk that didn’t wobble. I’d spend my days cataloging Alabama’s most beautiful mess of a history, from yellowing photographs to brittle Civil Rights-era pamphlets. It was a job with purpose, and I was good at it.

But good isn’t enough if there’s a little voice inside you whispering, “What if there’s more?” That voice doesn’t care how comfortable your desk chair is or how much you like the lunch spot next door. Mine kept asking me this unrelenting question: “What would happen if you left it all behind to chase a story?”

I felt guilty for even considering it. My family is the type that thrives on security. My mom and dad were teachers who patiently shaped young minds every year. My cousins all stayed close to home. I was part of a culture where “steady and safe” was a sensible mantra. I knew what it would sound like to them: “Carrie’s throwing away a good job to…to loiter on strangers’ porches?”

But I felt compelled. There were voices out there waiting to be heard—people who had lived through Alabama’s defining moments but whose stories hadn’t made it into the pristine museum galleries. Lives unfolding in quiet towns with no historic markers. And if there’s one thing I’ve learned, it’s that the stories not in the spotlight are often the ones you need to hear most.

Packing Up My Courage (and My Car)

So I did it. I quit my job, packed my car with a sketchy map, a borrowed tape recorder, and a snack bag that would make even a ten-year-old feel embarrassed. (Let’s just say I’ve never turned down a Honey Bun.) I had lined up visits with a handful of Alabamians whose names I’d gotten through very tentative connections.

I was as prepared as I could be—but emotionally? Not even close.

The first time I knocked on a stranger’s door, I got a polite but firm “No, thank you.” Actually, it was more like: “I don’t know you, and I don’t know why you care about a story from fifty years ago, but I’ve got better things to do.” Totally fair. I slunk back to my car feeling like I had gate-crashed an unflattering scene from “Sweet Home Alabama.”

Over the first few weeks, I learned this: trust is not built through introductions or credentials. It’s built through time, patience, and shared humanity. Eventually, I stopped approaching conversations with a mental list of exact questions and started listening for what people were actually trying to tell me about their lives.

One older woman sat me down one evening after a too-short response to my questions and said, “You don’t just dive into someone’s past like it’s a buffet. Sit with me. We’ll talk about what I want to talk about, and we’ll see if you’re ready to hear the rest.”

Point taken.

The Romance of Risk

Let me tell you something: this is what falling in love feels like, whether it’s with a person, a new career, or even yourself. It’s equal parts joy and fear. Standing at the edge of your comfort zone isn’t glamorous; it feels downright clumsy. It means handing over control and hoping for a connection.

Over time, those connections became magic. I heard devastating tales about loss and resilience from Selma to Cahaba. I sat on fraying couches, sipping the sweetest iced tea of my life, while someone recounted the heartbreak of a segregated childhood. I learned that laughter often pokes its head into the darkest stories, like sunlight through storm clouds.

One man told me how music had saved him, pulling his life in a completely different direction despite the weight of systemic inequality. Another woman walked me out to her yard to show me twisted tree roots that looked like her “family history”—equal parts beautiful and chaotic—a story written in wood.

Your “Greatest Risk” Moment

What I learned? Risks aren’t about dramatic endings with neat bows. They’re about uncomfortable middles. They’re about cracking yourself open, finding your limits, and recalibrating who you are.

And here’s the part where I flip this back on you: is there something quietly tugging at you right now? (Yep, I see you staring at that DIY pottery kit still in its box from last Christmas.) Maybe you don’t want to leap off a cliff, but could you lean over the edge just a little?

Here are a few practical takeaways for anyone teetering on the edge of “should I stay, or should I risk it?”

  • Start with what feels manageable: Risks don’t have to be life-altering immediately. Begin with a small “yes,” like trying salsa dancing lessons when you’re more of a two-left-feet individual.
  • Do it scared: Don’t wait until the fear goes away—it won’t. Take it along for the ride and show it you’re in the driver’s seat.
  • Expect awkwardness: Let me assure you—discomfort and self-doubt are part of the package. They are not evidence you’re failing; they’re proof you’re trying.
  • Seek connection: Every risk is easier to weather when someone’s there to listen. Find your support crew, whether it’s a best friend, a therapist, or that person from yoga class who always gets your sarcastic jokes.
  • Celebrate progress, not perfection: Your version of a leap may look tiny from the outside, but it’s monumental for you. Give yourself a round of applause anyway.

The Happily-Ever-After You Don’t See Coming

My greatest risk didn’t sweep me off to a glamorous life. I returned to Montgomery years later, knowing more than I ever could’ve absorbed behind museum glass. I didn’t do it perfectly or gracefully (don’t ask about the time I accidentally locked myself out of my car while hauling a box of cassette tapes). But I did it fully.

The relationships I built with the people I interviewed? Those changed the course of my life. Taking a chance on something uncertain solidified my career as a writer and made me fall, just a little, for the unpredictable.

Whatever leap you’re contemplating—whether it’s whispering an overdue “I love you” or walking into a new beginning—I hope this story gives you permission to jump. Not recklessly, but bravely. A little messiness only adds character to the best stories anyway.