The Fear I Conquered

Fear and My Flirtation with Control
If you had told my teenage self that one day I'd be writing about conquering fears, she would’ve responded with a bewildered “What fear?” from behind a plate of impeccably organized hors d’oeuvres at yet another Buckhead charity gala. See, back then, I prided myself on being fearless—or at least pretending to be. No stage too big for a speech, no room too intimidating for small talk.

But here’s the thing about fear: it loves subtlety. It doesn’t always show up wearing a horror-movie mask and dragging a chainsaw. Sometimes, it’s far sneakier, weaving itself into the corners of your perfectly curated life like a cobweb you convince yourself isn’t really there. For me, the eight-legged phantom in the room was this: I was terrified of failure. And not just the big, life-altering kind of failure, but any form of coming up short.

Bless my sweet Southern heart, I carried that fear like a family heirloom, polished and tucked away behind all my accolades and carefully orchestrated successes. But then, slowly and without asking for permission, life started to chip away at my veneer of control—in dating, in my writing, in ways that caught me off guard. Here’s how I faced it, cemented stronger connections, and let failure teach me what white-glove perfection never could.

Failing at Flirting: A Humbling Start
To properly understand my shift, you need to know about the first time I truly bombed at flirting. It was during my freshman year at Emory, and I was smitten with a philosophy major who somehow managed to quote Nietzsche and look good in boat shoes (a rare duality). Having grown up navigating social scenes with ease, I thought flirting would come naturally. Spoiler: it didn’t.

I attempted charm: “You know, your interpretations of existentialism are almost as layered as the pistachio soufflé at Canoe.”
His response? A blank stare, followed by, “What’s a soufflé?”

Mortified, I laughed it off, abandoned my efforts, and spent the rest of the semester avoiding boat shoes altogether. It wasn’t just a bruised ego. That interaction brought up a deeper fear—that I wasn’t good enough at something I had no excuse not to excel at. Why couldn’t I wing it like the cool, unbothered women I admired in Nora Ephron films?

Learning to Fail at Work (And Life)
The flirting incident wasn’t isolated. Life came for me again when I transitioned from writing for a glossy lifestyle magazine to my “dream” job of penning novels. Little did I know that moving from starry-eyed deadlines to the achingly quiet discipline of novel writing would be like swapping ballroom waltzing for breakdancing—underwater. I struggled with rejection letters, scathing critiques, and this gnawing sense of not being “good enough” right away.

One night, after my third manuscript rejection, I found myself in tears over a casserole I’d burnt while trying to watch re-runs of Sex and the City. (Not exactly Charlotte’s level of composure, but relatable, no?) I called my mom, who calmly said, “Perfection isn’t connection, sweetheart. No one relates to a façade.” She wasn’t talking just about dating or writing—she was talking about life.

Facing the Fear with Dating as the Mirror
Here’s the fascinating part: My reflections on fear often came back to dating. Relationships have this way of holding up a mirror to insecurities you didn’t know you had. Every awkward first date, mismatched expectation, and semi-casual “What are we doing here?” text exchange forced me to confront my fear of imperfection head-on.

Like when I once planned an entire date at a jazz café (complete with a monologue on Coltrane) only for him to say, “I kinda hate jazz…is there pizza?” Let me tell you, early Carrie would’ve taken that as a failure worthy of retreat. But instead, I laughed, got pizza, and, somewhere between bites, discovered how freeing it was to let the night—and myself—be imperfect.

How I Let Fear Teach Me

If you’re wondering whether I’ve fully conquered my fear of failure, let me save you the suspense: not entirely. That polished foundation I grew up on is hard to dismantle (also, perfectly suited for Southern humidity). But I’ve softened it. Here’s how:

  1. I Let Myself Be Laughably Bad at Something
    Whether it’s learning the violin at age 30 or starting a vegetable garden after killing three houseplants in one summer (RIP to my ficus), I’ve embraced the art of being hilariously, spectacularly bad. It’s good preparation for when life decides to hand out curveballs instead of comfort zones.

  2. I Redefined Success
    Success isn’t just ribbon-cutting ceremonies or five-star reviews. It’s the conversation you have on a park bench where you truly connect. It’s the fun of trying, the joy in the failure. (Also: You can survive someone telling you they hate jazz. Truly.)

  3. I Let People See Me Scramble
    One of my biggest fears—or so I thought—was that people would be disappointed to see me fail. But funny enough, letting a date or a friend witness me misstep has often led to greater connection, not less. Vulnerability turns out to be weirdly attractive, go figure.

Why It’s Okay to Fear (and Fail Anyway)
If you’re reading this and feel like life (or love) demands an excessive level of togetherness, I’m here to say it doesn’t. In fact, it rewards experimentation, even if it means laughing when your date would rather eat greasy pizza than hear a saxophone solo.

Fear, as I’ve learned, isn’t the saboteur. It’s the push we need to live more authentically—to write that sloppy first draft, to navigate a wildly messy heartbreak, to let ourselves be real even in the face of pasta sauce stains or a missed opportunity. Flirting, failing, and all those other scary steps don’t just pave the way for growth; they are growth.

So yes, I used to be afraid of failure, but these days, I flirt with it pretty regularly. It’s a dance I’ve learned to stumble through—with or without jazz in the background.