How's the Writing Going, Cheryl Strayed?

“I love writing. I really do. Even though I often hate it at various points in the process. Learning to accept that has been so important to me.”

Left, Cheryl Strayed, photographed by Holly Andres; Right, Strayed’s advice collection, Tiny Beautiful Things, which recently has been rereleased and made into a HULU series.

CHERYL STRAYED is the author of the #1 New York Times bestseller Wild: From Lost to Found on the Pacific Crest Trail, which has sold nearly five million copies worldwide and was made into an Oscar-nominated major motion picture. Her book Tiny Beautiful Things has been adapted for a Hulu television show by the same name that launched April 7th 2023. In 2016, Tiny Beautiful Things was adapted as a play that has been staged in theaters around the world. Strayed is also the author of the critically acclaimed debut novel, Torch, and the collection Brave Enough, which brings together more than one hundred of her inspiring quotes. Her award-winning essays and short stories have been published in The Best American Essays, the New York Times, the Washington Post Magazine, Vogue, Salon, and elsewhere. She has hosted two hit podcasts, Sugar Calling and Dear Sugars, which she co-hosted with Steve Almond. She lives in Portland, Oregon.

SARI BOTTON is the author of the memoir in essays, And You May Find Yourself...Confessions of a Late-Blooming Gen-X Weirdo. She is the former Essays Editor for Longreads, and edited the bestselling anthologies Goodbye to All That: Writers on Loving and Leaving NewYork and Never Can Say Goodbye: Writers on Their Unshakable Love for New York. She teaches creative nonfiction at Bay Path University and Kingston Writers' Studio, and is the Writer in Residence at SUNY New Paltz for Spring, 2023. She publishes Oldster Magazine, Memoir Monday, and Adventures in Journalism.

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*A version of this interview was originally published in November, 2022 at Catapult. (RIP Catapult!)

This is a column called How’s the Writing Going? It’s the question no writer wants to be asked—but which every writer wants to ask others. We want to know that other people are struggling the same way we are or to learn other writers’ hacks and antidotes for blocks and other challenges.

Here I chat with Cheryl Strayed about why writing is always hard—even when there’s no pandemic—and how to keep doing it anyway.

Sari Botton: Cheryl, on August 6th, 2020, you tweeted, “Writing is Hard. Dammit.” When I saw that, I felt so validated because I was in the middle of working on my memoir, and every day I had to basically trick myself into sitting down and writing. Like everyone else, I was traumatized, and struggling to write because of that. So, when I saw you admit to struggling, I thought, Okay, I'm not alone. When you tweeted that—what you were struggling with? 

Cheryl Strayed: Well, first of all, I would say writing is always hard. So, this wasn’t a  revelation that was strictly induced by the pandemic. I’ve learned that difficulty is part of the experience of writing for me. And I would say that’s common. Very few writers are like, You know what? Writing is easy. But the pandemic for me—I mean, not that it's over; when I say “the Pandemic,” I mean those first couple of years, especially that first year-and-a-half –it was so incredibly difficult. I have two teenagers and they were in online school for a year and a quarter. They were home all the time in an era when they wanted to be out with their friends. The parenting was extremely hands-on, in ways almost like being back to the era during which my kids were toddlers. There was a lot of angst and turmoil and seldom a sense of quiet or solitude in our house–which makes writing quite difficult. The distractions were real and many. . 

SB: The pandemic made me very aware of a certain amount of privilege I have as a non-parent. So many people, women in particular, had to suddenly become schoolteachers in their own homes, while also trying to make a living over Zoom. That must have been so hard. Not to mention what a scary time it was.

CS: It was so scary and my kids struggled and that made writing even harder. 

SB: Were your kids toddlers when you wrote Wild? 

CS: When I sold my first book, Torch, I was three months pregnant with my first child. By the time it was published, I had two kids under the age of two–they’re seventeen months apart. At the time I thought, How on earth will I ever write another book? Because it was so hard to write Torch without kids, I couldn’t imagine how I’d do it while taking care of two children. 

But I did. They were really little when I wrote Wild. I pieced it together–trading off childcare with my husband, Brian, who’s a documentary filmmaker, or writing while they were napping or when they were at the preschool they attended for two-and-a-half hours a day a few days a week. I do look back and wonder, How did I even do that? I would sometimes go to these “residencies,” as I would call them—self-made residencies where I’d check into a nearby hotel for two nights. I’d be away from my family for forty-eight hours, and I would write like a motherfucker. So much of Wild got written that way. I sold Wild the year before I began writing the “Dear Sugar” column for The Rumpus, and I was doing the final revisions on the book while I was finding my way into this strange new gig of writing an anonymous advice column. Eventually, those columns were collected into my book, Tiny Beautiful Things, which was released in 2012, the same year as Wild. 

I’ve learned that difficulty is part of the experience of writing for me. And I would say that’s common. Very few writers are like, You know what? Writing is easy.

SB: Wow, it’s been ten years for both books. And now Tiny Beautiful Things was just re-released—a new edition with additional columns. Plus it’s been a stage play, and it’s also a Hulu show starring Kathryn Hahn, which you worked on. Oh, and you have a Substack newsletter, Cheryl Strayed’s Dear Sugar. There was a “Dear Sugars” podcast, too, that you did with the original Dear Sugar who passed the column on to you, Steve Almond.

I remember when you were writing those original columns anonymously as “Dear Sugar.” I’d wait all week to get to Thursday so I could read the next one as soon as you published it. Did you have an easier time writing and publishing Tiny Beautiful Things than Torch or Wild?