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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.

I started again.

I started from a place of where I thought my book should start. I started with what was most appealing to me, instead of what was most logical. It was still terrifying—this was still the biggest project of my life—but I consulted the outlines far less…and the writing came easier. The story opened up before me. I could see how scenes would give way to narrative sequences and then whole chapters. I was glancing at my outlines occasionally but I was also ignoring them when—and here was the weird part—when the story told me I should.

Suddenly the story opened wider. The writing flowed now. I was writing faster and more per day than I ever had but the writing wasn’t bad, was in fact decent, at times some of the truest stuff I’d put on the page. Stuff that sounded like my best thoughts.

I woke up each day looking forward to that day’s work. That had happened in the past as well but the difference now was how experimental I’d become with tone and style. Just trying an idea to see if it worked. Getting more courageous with what I put on the page.

My friend and former colleague Tom Junod once told me he likes to listen to The Doors when he’s writing, not because he loves The Doors but because Jim Morrison…went there. He wrote songs that were long and overwrought and filled with a mysticism even Morrison didn’t grasp. Some of those songs were terrible. Some of them were the most iconic anthems of the 20th Century.

The lesson for Tom was to always err on the side of big and bold, especially in a first draft. A good editor will catch where you’re pretentious or just flat out wrong. But try stuff. Let the process control you as much as you control the process.

I finished the first draft. It was better than I thought, not perfect (and I still had those tendencies) but good enough to hand to my editor. When I got the notes back they weren’t as numerous as I expected. My first draft was like the initial pass a sculptor takes at a mound of clay. Nothing was finished, but the potential was evident.

I tinkered again. It was akin to the sort of tinkering I’d done at the outset, when I was flailing, but now with a draft on the page I saw more clearly what needed to improve. My perfectionist instincts flourished. They could isolate a problem and work, work, work, the fix. I had never written under this sort of process.

I never wanted to write any other way.

The second draft became a third and even more finely dissected piece of writing. My inner perfectionist thrived. So did the book. It kept improving.

When I at last sent it back to the editor and then onto the galleys to be published, I was thrilled with it. This was the best work I’d done.

When the book debuted, it got rave reviews, became a №1 best-seller on Amazon, and was optioned to be made into a movie.

More than that, it changed the way I look at writing and life. There is always time later on to perfect the work you do now. The main thing is to work—today, in this moment—with a confidence and boldness that’s true to yourself, that honors all of who you are and would like to be. Relax and rip. If you overshoot, you can correct it. It is much easier to turn it down than dial it up.

With every blank page and blinking cursor I face in life, I have one motto now:

Channel the inner Lizard King.

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