How To Counter the Perfectionism That Kills Creativity

And let it alllll hang out.

I was a Type A person with perfectionist tendencies and about to do the work my entire career had been in service of: the writing of my first book. From my research I’d written thousands of pages of notes and hundreds of pages of notes on those notes—stuff that was the best of the best, sure to find a home in future paragraphs, paragraphs which had themselves already been meticulously outlined and lived within larger chapter outlines, all of them residing quite orderly in a massive folder I called, with a sense of Manifest Destiny, “The Book: Structured.”

I started in.

The writing didn’t flow though. The rigidity and order that had in the past, in the magazine pieces I’d written, freed me to focus on the sentences now chained me to ideas and narrative progressions that didn’t—I don’t know—feel right. Maybe it was the scale of the undertaking. A book is so much longer than a 6,000-word feature. But I couldn’t place what was off and thought I could fix it by focusing even more on the sentences before me. I stared at the screen. Haggled with myself over word choices. Wrote and rewrote and wrote again the same sentence, the same paragraph, the same page, losing hours and then days and constantly searching for the thing, that feeling, which told me what I had…had potential.

The feeling never came. The writing I produced wasn’t terrible exactly but was dutiful, predictable. Limp. Which meant it was also, strangely, seductive: thisclose to being what I needed. So each day I tried again to improve it and follow the structure I laid out but each day I fell further behind.

The deadline drew close, and then closer. I freaked out a little, and then a lot.


I’ve never had writer’s block and wouldn’t call what I experienced in those days and weeks writer’s block, but I would say it shook me. How I found my way has been perhaps the best lesson of my writing life, and one that’s applicable to any creative pursuit of mine, or yours, or really any pursuit at all.

I wasted weeks tinkering before I had what Southern Baptists call a Come To Jesus. The moment when I reassessed everything.

I realized the problem wasn’t the sentences. The sentences, even beautiful sentences, would only be as good as the narrative they served. I was focusing on the sentences as a way to not focus on the larger issue: My outline sucked.

That terrified me. I had spent all this time outlining everything because I always outlined everything—it comforted me to outline everything—and on the biggest project of my life the outline wasn’t right?! Should I start again? If I started again how much time would I lose? How would I know that a new outline would get me to a better spot?

I had no answers. If anything I just had more questions, which dug ever deeper into my psyche. Why was I so obsessed with outlining everything? What was I really trying to control?

Yeah: what was I trying to control?

Well, and this took days and long walks and a couple sleepless nights to arrive at an answer, but I was trying to control the trajectory of my career, and life. And yet the trajectory of my career and life—these were outside my control. Yes, I could put in the time and do what I saw as great work but I had no sway over how the reading public would respond to it, just like I had no sway over whether, say, the tree in my backyard might fall in a storm onto my garage or the makeup of my wife’s genetic code might one day lead her to develop cancer. Life doesn’t give two shits about how much you want to control it. Life, the particulars of it, everything outside my thoughts and actions, which were the only things I could control—life would do to me what it wanted. The only thing I could do in return was respond to any shit storm with courage and objectivity.

So what was the objective truth of my book?

My outlines were really a metaphor for my life: I was holding on so tight to what I’d created that I was slowly strangling it.

So I let it go.