What they don’t tell you about failure is how deeply personal it feels when you’re standing in the middle of it. Back in my early twenties, fresh out of grad school and armed with an overly inflated sense of capability, I thought I could outwork, outsmart, and outrun every obstacle in life. Turns out, life doesn’t operate on hubris. It operates on lessons, and sometimes those lessons crash into you like a semi on the I-64. Spoiler alert: you will not win that collision unscathed.
My first big lesson in failure came disguised as a dream—that dream being a local storytelling event I ambitiously organized in my hometown in West Virginia. I imagined it as our slice of literary glory, Piedmont’s answer to NYC’s The Moth, something that would celebrate Appalachian voices and foster connection in a place that often feels overlooked. The idea warmed my chest like moonshine on a winter night. But reality? Reality had other plans.
The Fantasy vs. The Faceplant
In my head, it all looked perfect. Locals would line up at the rec hall as fiddles played softly in the background. There’d be laughter, heartfelt stories, homemade pierogis from Mrs. Talbot (who was kind enough to offer her catering services), and maybe even a strong sense of what some folks in these parts like to call “revival.”
But here’s what really happened:
- The “crowd” consisted of my parents, my college buddy Kyle, and three curious town regulars who likely came for the pierogis—and then left when they realized there wouldn’t be beer.
- Two of the four storytellers canceled last-minute: one due to a plumbing issue (which, honestly, might’ve made for a more riveting story than anything on our mic that night), and the other ghosted entirely, likely due to my lack of Instagram marketing savvy.
- The one mic we had kept cutting out, meaning my mother was forced to stand up and tell her story about a haunted coal mine shouting across the room like she was at Sunday potluck.
If I had to sum it up in one image, imagine a party balloon being slowly deflated while John Denver’s “Take Me Home, Country Roads” plays in the background. Yep, that was the vibe.
Failure Hits Different
The next day, I woke up in the funk of post-failure regret, which, if bottled, would probably taste like instant coffee stirred with disappointment. I replayed every missed opportunity and rookie misstep a hundred times over. Why didn’t I recruit more speakers earlier? Should I have brought my uncle’s old banjo to spice things up? Was it my bad taste in flyers (designed on Microsoft Word, by the way—look, money was tight)?
But here’s the kicker: It wasn’t just about the failure itself. It was about the weight of letting down the people I wanted so badly to uplift. Growing up, Appalachia taught me two truths—how deeply community matters and how easy it is to feel like you’re constantly under the lens of judgment. This wasn’t just about a failed event; it was about what it meant to embrace my roots and make something good grow here—something I’d thoroughly botched.
Except...maybe I hadn’t botched it as badly as I thought.
What I Learned When I Stopped Kicking Myself
When I finally stopped wallowing long enough to reflect, I noticed something unexpected: I actually learned a handful of lessons that would stick with me long after I recycled the leftover flyers. Here’s what failure taught me:
-
Big Dreams Need Small Steps.
I treated that event like building the Sistine Chapel, forgetting that Michelangelo probably didn’t just show up with a paintbrush and vibes. Creating something big means laying a foundation—and accepting that it doesn’t have to be perfect right away. -
Humor Is a Survival Tool.
Listen, if you can laugh about your mom bellowing ghost stories to half a dozen pierogi eaters, you can laugh about almost anything. Humor helped me find clarity—and gave me the courage to try again. -
Community Is What You Cultivate.
After the event, Mr. Talbot (a man of few words who speaks mainly in weather-specific phrases) told me, "Well, son, y’did something. And that’s more’n’ most folk try." Truth is, even showing up matters. The five people who came? They were there, and maybe that’s what counted most. -
Failure Won’t Kill You.
At most, it bruises your ego—and your wallet if you’re unlucky enough to foot the pierogi bill. But you’ll survive, and sometimes survival is victory enough. -
Reframe the Story.
I thought my event would be a story of success. Turns out, it’s a better story as a cautionary tale—one I can now tell to help others avoid their own small-town debacles.
How Failure Made Me Resilient (and Weirdly, a Better Partner)
Now, you might be wondering, “James, what does organizing a public storytelling event in West Virginia have to do with relationships or dating?” The honest answer? Everything.
When I look back at that failure, I realized what it taught me wasn’t just practical advice but emotional wisdom—wisdom I later carried straight into my personal life. Relationships, like community projects, run the risk of messy breakdowns and unmet expectations. But they also thrive on effort, patience, and adaptability.
For instance, when my now-fiancée and I hit our first big fight, I felt this familiar pang of disappointment, like I’d stepped into the same frustrated version of myself that I was after the storytelling disaster. But then I remembered: failures aren’t endings. They’re just chapters. If you lean into imperfection rather than run from it, you always stand a chance of writing a different ending.
Building love—and connection—isn’t about being flawless. It’s about showing up, owning your missteps, and trying harder the next time (even if the “next time” involves twice as many pierogis).
Your Right to Fail Out Loud
So, here’s what I want you to know: whether it’s a dream project, a first date, or a last-ditch effort to save a relationship, failure is never the red light you think it is. Failure is a detour, sure—but it’s still part of the route. You can’t reach anything worth having without veering off course now and then.
My storytelling event didn’t pan out the way I envisioned—it wasn’t Piedmont’s version of The Moth, not even The Caterpillar. But it gave me something infinitely more valuable: resilience. It taught me that while I can’t control outcomes, I can control how I show up, time and time again.
So go ahead—fall flat, miss the mark, serve up your own embarrassing, microphone-failing flop. Just make sure to laugh when you look back. And who knows? You might even find your fiancée mid-flop, staring at you over burnt pierogis and thinking, This is someone who isn’t afraid to keep trying.
Because truthfully? That’s the real victory: staying willing to show up, failures and all.
