Messy Middles, Coffee Meltdowns, and Donut Truths: A Conversation with Kyle Holden, Author of “Someday Starts Today”

When Kyle Holden set out to write Someday Starts Today, a guide to getting out of your own way and starting before you’re “ready,” he didn’t expect the biggest obstacle would be… himself.

“Oh my goodness, yes,” he laughs, when asked if he had to take his own advice during the publishing process. “I hit a wall after my first edit. Suddenly, I wasn’t thinking about the message—I was chasing the perfect launch. Headlines, bestsellers, marketing plans. I lost sight of why I wrote the book in the first place.”

That “why” was simple: to help at least one person feel less stuck. But in chasing viral moments, Kyle nearly stalled out. So, he did what the book teaches—he made it small again. “I just focused on the next step. One page, one breath, one honest attempt at progress.”

This theme—of shrinking the pressure in order to keep moving—carried Kyle through the dreaded “ugly middle.” It’s the phase no one posts about: when self-doubt creeps in, and every part of the dream feels uncertain. “The messy middle convinces you that what you’re doing isn’t enough. That it’s not working,” he says. “But that’s actually part of the process. It has to be.”

Kyle’s smallest step was sometimes just scribbling a few sentences. Other times, it was closing the laptop and coming back later. “There’s a quote I love—‘If the next step feels too big, it is too big.’ So I made it smaller.”

Self-publishing came with its own tidal wave of choices. “It was like steering the ship while building it,” Kyle jokes. “There are no rules, just options. You have to decide what to listen to and what to leave behind.”

In Kyle’s case, that meant scrapping a lot of traditional content strategy in favor of gut instincts. “Content creation burns me out,” he admits. “So I leaned into what felt natural instead.”

One of his most unexpected creative choices? Including breathing exercises every 15 pages. “I wanted to help readers re-center. When you’re spiraling, it’s easy to stop absorbing. So I built in moments to pause.”

The most surprising story in the book? That came from a therapy session. “My therapist told me I was ‘should-ing all over myself’ and I burst out laughing. That phrase made it into the book—and it ended up being one of the stories I’m proudest of.”

Of course, the final stretch to launch wasn’t all breathing exercises and breakthroughs. Kyle faced formatting disasters, last-minute edits, and what he calls “peak imposter syndrome.” At one point, holding his newborn in one arm, he typed with the other. “Some nights, my writing session was twelve words and a sigh,” he says.

Despite it all, Kyle hit “publish.” And then came the weirdest part: the silence. “I didn’t tell anyone I wrote a book. Not even my family,” he says. “Because I was scared I wasn’t really an author.”

But on a random morning in a coffee shop, a friend saw the book on his table. “She froze. Looked at the name. ‘Wait, you wrote this?’ That’s when it hit me. Yeah. I did.”

Even now, Kyle wrestles with starting new things—like a zine about food, music, and joy that lives in his head “perfectly.” But he reminds himself: dreams are loud, but progress is quiet. “You just have to take a step. Even if it’s messy.”

When asked the final, vital question—what kind of donut captures his personality—Kyle doesn’t hesitate. “A yeast donut with chocolate glaze, sea salt flakes, and a mango drizzle. Classic, but with some unexpected warmth.”

Just like the book.

Kyle Holden’s book Someday Starts Today is available now wherever books are sold.

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