Cover Photo: This header image has a picture of Cheryl Strayed sitting in a chair on the left hand side and a cover of her newest book, TINY BEAUTIFUL THINGS, on the right hand side.
Photograph by by Heather Andres/book cover via Knopf Doubleday Publishing Group

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.”

New York TimesWild: From Lost to Found on the Pacific Crest TrailTiny Beautiful ThingsTiny Beautiful ThingsTorchBrave EnoughThe Best American EssaysThe New York TimesThe Washington Post MagazineVogueSalonSugar CallingDear Sugars

Sari Botton: Cheryl, on August 6, 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, . When you tweeted that, what were you struggling with?

You know what? Writing is easy

SB: The pandemic made me very aware of a certain amount of privilege I have as a nonparent. 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.

SB: Were your kids toddlers when you wrote Wild?

Torch How on earth will I ever write another book?Torch

WildHow did I even do that?WildWildTiny Beautiful ThingsWild

SB: Wow, it’s been ten years for both books. And now was just rereleased—a new edition with additional columns. Plus it’s been a stage play, and soon it will also be a Hulu show starring Kathryn Hahn, which you’ve been working on and which will be out in early 2023. 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 than or ?

Tiny Beautiful ThingsI’ve got to write a column. I can’t write a column!Isaac FitzgeraldTiny Beautiful Things

Oh, I’ll write it for a while, then hand it on to another writer

SB: It seems like something that was a perfect organic fit. And that’s probably why it has naturally appealed to so many people and had so many lives, in different formats. I’m also so excited for the Hulu show.

SB: I think you really do embody Sugar. I remember when we were both in The Rumpus Women calendar in like, 2011? I dressed as the Lena character from the Kundera novel . You emailed me then and wrote, “I’m Dear Sugar. Shhhh.” I was like, Oh, wow. Now I know who Sugar is! And I wasn’t allowed to tell anybody. I felt extremely special!

Before Dear Sugar, did you ever envision yourself as an advice columnist?

SB: Oh, definitely. I’m actually getting ready to launch an advice column on Oldster Magazinecalled Ask the East Village Yenta, who is me.

SB: I am someone who people come to for advice. Honestly, though, sometimes I can be a little too blunt in delivering it. I’ve had some rifts with friends over the years because I can be a little indelicate in delivering a platter of truth, which is something that I’m learning to do differently. Have you got any tips for a burgeoning advice columnist?

I empathize. I believe in your goodness. I believe you have the capacity to answer this question yourself.

SB: This is great advice. Thank you! So, what other kinds of things have you been writing lately?

This TellingLolita in the Afterlife: On Beauty, Risk, and Reckoning with the Most Indelible and Shocking Novel of the Twentieth CenturyJenny Minton Quigley

SB: That’s brilliant.

SB: Let’s talk about process, especially when the writing is hard. As I said, I have to trick myself into writing in so many different ways. When I’m stuck, I use the pomodoro method, racing a timer for even just five minutes. After five minutes, I’m almost always primed to do more. Sometimes I have to journal to talk myself into writing. What are some of the things you’ve had to do to get yourself into the chair and actually write?

I’m not going to sweatThis is going to be easy and I’m going to enjoy every minute of itThere are going to be times that this burns and that I look at the clock and think, we’re only twenty minutes into this sixty-minute class and I want it to be over.I’ll put up with that part of me and that part of my processOh yeah, this actually helps me do well

This is too hardI can’t do this. I’m going to give the money back. Just fail.No, I don’t want to do that. I want to push through.What is wrong with me? Why is writing so hard?

What would it mean for me to change? What would Cheryl the writer be like in this new iteration without the agonizing and anxiety? I can’t wait to get started! I’m such a good writer. I’ve got this covered!

SB: In a similar vein, when I was freaking out as I was writing my book, often I had to give myself permission to quit. At three thirty in the morning, when I was staring at the ceiling, the only thing that would allow me to go back to sleep was the idea that I could just walk away from my book. Of course, in the morning, I’d get back to chipping away at it, and I no longer wanted to quit. But giving myself that out really helped.

Well, what is the worst-case scenario? And let’s see if I can live with that.

SB: It’s funny; I’m having sort of the opposite thing happen now, where I’m still wrestling with old fears that have recently been invalidated or resolved. For so long I didn’t finish writing my memoir because I was afraid of my family’s reaction. But then my family loved the book, as I wrote about here. But I’m still operating with that old fear hanging around me. It’s almost like an old friend or a security blanket that I carried around with me—or my excuse. Like, Without that, I almost feel more naked now. I’m having to reorient myself as a writer, and it’s a different kind of scary.

when you interviewed me many years ago

SB: What are you working on now?

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 a contributing editor at Catapult, and the former Essays Editor for Longreads. She 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 Catapult, Bay Path University and Kingston Writers' Studio. She publishes Oldster Magazine, Memoir Monday, and Adventures in Journalism.

Photo credit to Sylvie Rosokoff