Sometimes, writing is like picking the perfect trail for a day hike. The morning air hums with potential, your backpack is loaded with snacks (because snacks are critical), and the mountains seem endlessly inviting. Other days, the path feels more like scrambling up one of those impossibly steep Wasatch slopes at the tail end of July, with no shade or clear endpoint in sight. The hardest piece I’ve ever written? It was one of those uphill battles—one with a surprising twist by the time the summit came into view.

Let’s rewind.

The Tangled Terrain of ‘Should I Write This?’

A couple of years ago, I was asked to write about relationships—specifically, how faith shapes love and how both evolve over time. As someone raised in an LDS family where relationships were spoken about with a blend of practical wisdom and ideals perhaps more sparkling than a Salt Lake City snowfall, I figured it would be a breeze. After all, I’d spent much of my life grappling with how people connect, commit, and occasionally combust in the face of expectations. How hard could it be?

Turns out, pretty hard. Hard in the way trying to assemble Ikea furniture without the instructions is hard. There were existential questions I couldn’t ignore: Should love defer to what is expected, or should it push against the walls of convention? Was I using my own memories like tiny wrenches, tightening a story that fit too conveniently? I realized I wasn’t just writing about relationships—I was untangling my own.

Anyone who’s ever stared into the stark glow of a blank Word doc or stood in front of a potential date wondering whether to go for the hug or handshake can appreciate the sensation: this terrifying mix of anticipation and self-doubt. One false move, one bad paragraph, and the whole thing could tumble into irrelevance.

The command from my editor was clear: Make it relatable. "Bring the readers in with a funny story," they urged. But truthfully, humor felt miles out of reach. My brain kept spiraling, wondering if I should admit how my view of love had been shaped—or misshaped—by a parade of talks about eternal marriage, ward youth dances, and a misguided teenage crush that led me to fast for spiritual clarity (spoiler: it didn’t work).

Just Add Humor? Easier Said Than Done

Eventually, I started with a memory. When I was 13, I managed to convince myself that one of the girls in my school was my “soulmate.” This delusion was not based on much—our shared interest in poetry and the fact that she didn’t seem entirely repulsed by me—but hey, it was enough. I spent weeks crafting what I considered the apex of romance: a heartfelt, hand-written letter explaining exactly why we were destined to be together. In retrospect, it read less like a sonnet and more like a Hallmark card had been run over by a tractor.

When she very kindly (and I do mean kindly) told me she didn’t feel the same, I sunk into what anyone over the age of 12 would recognize as a hormonal drama spiral. I couldn’t see it then, but that moment was less about rejection in the traditional sense and more about me mistaking infatuation for compatibility. Ah, young love.

This story trickled into the piece, sandwiched between larger ideas about how love isn't always the result of grand destiny but often grows from very unromantic things: compromise, shared values, and learning to laugh about burnt dinners. The beauty, I realized, is that love can flourish not in the declarations of star-crossed fate but in the spaces where people work to truly see each other. While that realization was profoundly moving to write about, pulling it out of myself felt like yanking a set of awkward roots embedded in soil long undisturbed.

Tears, Rewrites, Repeat

When I turned in the first draft, my editor (rightly) called me out. “It’s good,” she said. “But where’s you in this? You have this way of making the abstract personal. Right now, it feels like Caleb looking down from 30,000 feet, not like Caleb hiking the trail itself.”

Her point hit harder than the sunburn I got hiking Angels Landing in Zion without sunscreen (never again). She was asking for vulnerability, real stakes—not just safe observations but something I felt uncomfortable admitting even to myself. That’s when it clicked: This wasn’t just an article. This was my chance to be honest with readers and with myself, even if my honesty didn’t come wrapped in perfect prose.

So I rewrote it. And rewrote it again. And again. Along the way, I threw in more personal anecdotes, like the time I realized I was making excuses for not dating a wonderful woman simply because her background didn’t align perfectly with what my family might have envisioned. Or how stepping back from my faith helped me understand that unconditional love isn’t always synonymous with conformity. Every revision was messy, like reheating leftovers that just didn’t taste quite right no matter how many seasonings you added.

But eventually, I landed on something I felt proud of—not perfect but true. Laced with humor, humility, and more than a little wrestling with my cultural wiring, it became the piece I needed to write, even if it wasn’t the one I’d expected.

Lessons from the Trek

So, what did this all teach me about love, writing, and everything in between? Three big takeaways stood out:

  • Rejection Doesn't Define You. Whether it’s being turned down in middle school or feeling like you’ve missed the relational benchmarks life imposes, rejection is less about your worth and more about life nudging you in a different direction. It’s okay to sit with discomfort—it’s fertile soil for growth.

  • Love Evolves. When I was younger, I thought of love as an endpoint—something you achieved after making the “right” choices (or fasting for clarity). Now I see it as a constant evolution, a practice rather than a prize.

  • Honesty Wins. The hardest truths are the ones we hesitate to vocalize, especially to ourselves. But when we name them, we make room for shared understanding and deeper connection.

Writing the toughest piece of my career felt like an exercise in vulnerability, uncertainty, and a fair dose of overthinking. But just like any relationship worth its salt, it also taught me more about who I am. Maybe that’s the point—it’s not about the easy trails, after all. It’s the steep hikes, the moments when you pause to catch your breath and realize you’re nowhere near done, that stay with you long after the journey ends.