There’s something about cold pizza at a boardwalk carnival that makes you think, “This is either peak joy or a frozen snapshot of chaos.” Writing this piece felt a lot like that. It was exhilarating, messy, and stretched my soul in every direction, much like trying to eat funnel cake on a windy day. But, to tell you about the hardest piece I’ve ever written, we have to rewind to a moment in my life when the stakes felt sky-high—or at least towering higher than the ferris wheel on Ocean Boulevard.

Setting the Stage: A Love Letter to Imperfection

Picture Myrtle Beach in late October. The tourists have mostly packed their bags, the air smells faintly of salt and endings, and the boardwalk starts to belong to the locals again. I’d been tasked with writing a deeply personal essay about heartbreak—more specifically, finding closure in a breakup that leaves you feeling wrung out, like beach towels left to dry on sagging laundry lines.

I’ll be honest: I wasn’t ready. My editor (bless her relentless encouragement) called it “a test of vulnerability,” but it felt more like trying to recite slam poetry while standing knee-deep in a riptide. The relationship in question had been short-lived but intense—the literary equivalent of a sparrow hitting a glass window. We didn’t see the collision coming, but once it happened, it was impossible to walk away unscratched.

Act I: The Blank Page Dread (AKA Overthinking 101)

If you’ve never stared at an empty Word document and felt your heart race, consider yourself lucky. For a week, I wrote nothing but fragments. Half-finished thoughts, memories I wanted to shape into something coherent, but they slipped between my fingers like wet sand. On bad days, the inner monologue sounded like a poorly reviewed stand-up show:

“Kaylee, people don’t want another Eat, Pray, Love rehash. Get it together.”
“Why don’t you spend less time describing sunsets and more time being, I don’t know, LEGITIMATELY USEFUL?”

The problem was that this breakup wasn’t even about “the one that got away.” It wasn’t epic, Romeo-and-Juliet level drama. It was just ordinary heartbreak—messy, confusing, its edges both sharp and blunt. How could I make a story out of something so pedestrian?

Here’s the thing: The fear of writing is rarely about the writing itself. It’s about what happens when you finally put the truth down on paper, and suddenly, there it is, glaring at you. My truth was that I wasn’t angry about the breakup. I was ashamed. I’d let parts of myself shrink in that relationship—parts, frankly, that I was still trying to get back.

Act II: The Turning Point (With a Splash of Sass)

Halfway through this emotional slog, I remembered something my grandmother used to say whenever she saw me sulking over a teenage melodrama: “Even oysters need grit to make pearls.” Sure, at the time, I rolled my eyes hard enough to see my own brain, but the point stuck. Difficulty doesn’t have to just sit there, inert—it can transform you.

Once I reframed that breakup as a story not of loss but of growth, the piece started to reassemble itself. Slowly, I began untangling the narrative, with the same determination required to undo the tiny necklace knots I’d accidentally made in college (and still, somehow, haven’t learned to prevent).

I asked myself:
- What did this relationship—and its messy ending—teach me about boundaries?
- How did I confuse sacrifice with compromise, and which corners of myself felt hollowed out as a result?
- Most importantly: How do you rebuild?

I leaned into the watery metaphors I grew up loving—of ebb and flow, hurricanes followed by stillness, and tides rediscovering a shoreline they once abandoned. There was catharsis in treating my heartache like an oyster’s grit. Maybe this breakup would create something worthwhile too.

Act III: Lessons Learned (Pass the Life Preserver)

When the piece finally came together—triumphantly titled something self-deprecating like “How to Lose a Guy Without Incidentally Losing Yourself”—I realized some profound truths that applied far beyond the pages of that article. Here they are, for anyone who might be in the thick of their own rebuilding phase:

  1. Heartbreak Isn’t Linear. Some days you feel like a dolled-up megastar who just aced their karaoke rendition of Beyoncé’s “Irreplaceable.” Other days, you’re crying over leftover Chinese food because it reminds you of movie nights you used to share. Both are valid. Let grief ebb and flow on its terms.

  2. Boundaries Aren’t Walls, But They’re Necessary. Relationships should stretch you but never break you. If someone pokes at your edges so much that you become unrecognizable, it’s time to evaluate whether the wind is blowing you off course—and recalibrate.

  3. Don’t Wait for Closure. You’ll Know When You’re Whole. Closure isn’t a neat ribbon tying everything together; it’s waking up one morning and realizing you haven’t thought about them in days. It’s loving your own company again and letting the emptiness fill with something softer—like hope.

  4. Laugh When You Can. Honestly, one of my breakthrough writing moments came when I compared my ex to a boardwalk fortune teller who makes vague promises and collects your quarters. Humor, even at its gallows, has a way of bringing clarity.

Act IV: The Published Piece (And a Side of Existential Dread)

Publishing that essay felt like walking into a crowded beach bar wearing nothing but a sarong and good intentions. Vulnerability is terrifying, especially when it’s immortalized online. For days, I was convinced I’d made a mistake. What if people sneered at my oversharing? What if it came across as self-indulgent?

But then came the messages—from strangers, friends-of-friends, and even old high school acquaintances. People wrote to say, “Thank you. I needed this,” or “Your grit versus pearl metaphor hit me square in the chest.”

I realized the hardest pieces to write are often the ones people most need to read. Honesty, even when messy, has a way of resonating. And this wasn’t about me anymore—this was about readers seeing themselves in my story.

Sunset-Sloshed Takeaway: When Writing Hurts, Keep Going

It’s always easier to tell someone else’s story. Writing my own felt like spilling a Mason jar of sea glass across the floor, trying to put the pieces back into some order that made sense. It wasn’t about perfection; it was about honoring what had been broken and reframing it as something worth keeping.

So, here’s my parting thought: If you ever find yourself staring at a blank page, too paralyzed to start, remember this—it doesn’t have to be pretty, or polished, or Pulitzer-worthy. It just has to be yours. The hardest stories to write often hold the most beauty, not because they’re neat, but because they’re true.

And sometimes, it’s in those messy, honest stories that we find our way back to ourselves.