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.”

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.

Cheryl Strayed is the author of the number one 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 is currently being adapted for a Hulu television show that will be released in early 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 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 cohosted with Steve Almond. She lives in Portland, Oregon.

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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, Okay, I’m not alone. When you tweeted that, what were you 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 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.

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.

SB: Wow, it’s been ten years for both books. And now Tiny Beautiful Things 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 Tiny Beautiful Things than Torch or Wild?

CS: The only way that it was easier to write Tiny Beautiful Things is that I was writing the columns every week, so I didn’t know I was writing a book until I’d written it. It helped that I had a deadline. Each week I’d think, I’ve got to write a column. I can’t write a column! Then I would write it, usually overnight, and I would send it to Isaac Fitzgerald, who was the managing editor at The Rumpus at the time. It would go up on Thursdays at noon, and so often I would send it to him at like 11:30 a.m. I always say that Tiny Beautiful Things is the book I wrote by accident.

And here we are, more than a decade later, and the book has had a big life, being adapted for the stage and the screen, and now there’s a new edition. It came out this month, and it includes a new preface and six new columns.

I never imagined when I began writing the Dear Sugar column that it would become such an important part of my writing life. When I took it on, it was really just a fun thing. I was being paid nothing for it. And it was anonymous. When I started writing it, I thought, Oh, I’ll write it for a while, then hand it on to another writer. And then pretty quickly I realized that was impossible. I gave it everything from the deepest parts of me—same as I do in my other writing—and so I couldn’t pass it on. Sugar was me. I could no sooner hand over anything I wrote as Sugar as I could hand over anything I wrote as Cheryl Strayed.

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.

CS: Thanks. I’m excited too. The process of adapting it for television has been so interesting. I’m one of the writers on the show, and also an executive producer. The wonderful Liz Tigelaar is the showrunner, and I’ve learned so much from her about writing television. We had a writers’ room of nine amazing humans that we did via Zoom. And Kathryn Hahn is brilliant in the role. I can’t wait for you all to see it. I feel constantly astonished by the places the Dear Sugar column has led me.

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 The Unbearable Lightness of Being. 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?

CS: No. Honestly, when I said yes to the column, I didn’t really read advice columns. I mean, I’d read them occasionally if I came upon them in a newspaper or magazine, but I wasn’t somebody who followed advice columns. And I had never gone through therapy, didn’t read self-help books—and still don’t. But what’s true is that I believe in the power of story to heal us. Like, actually.

The most consoling and illuminating and helpful thing to me in times of trouble is reading—reading the works of people who write honestly and deeply about the truest parts of what it means to be human. And so, as Sugar, I decided to do that. I trusted that using story would be a helpful form of advice because it’s a story that has saved me, over and over again. Dear Sugar is an advice column, but the columns are also essays about life, wouldn’t you say?

I believe in the power of story to heal us.

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

CS: I love it.

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?

CS: It’s really important for people to feel like you’re not judging them, like you’re rooting for them. As Sugar, I always try to say, “I know this is maybe hard to hear, but I am so much on your side.” I use the phrase “unconditional positive regard, ” which I’ve written about in one of my columns. Even if I think the person’s making a mistake or kind of being a jerk, I hold them in unconditional positive regard. What that means is: I empathize. I believe in your goodness. I believe you have the capacity to answer this question yourself. That’s essentially the center of where I come from as Sugar. And also: I’m not above you. I’m not the wise person who knows. I’m not holding the platter of truth. I’m not able to serve it to you. No, I’m sitting around the table with you, also trying to eat from that platter of truth. Historically, advice columns have been written from a place of superiority—the advice giver knows what the advice seeker does not. From the beginning, I conceived of it differently. I sit horizontally in relation to those who seek my advice, not above them. I think that’s made a world of difference. A lot of people feel loved by Sugar, even if I say something that’s hard for them to hear.

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

CS: I’ve written so many different things over these last several years. I wrote a long short story for Amazon Originals called This Telling that was published as an ebook. It was fun to return to fiction, my first love, and to write something in which I’m not anyone in the story. I wrote another piece of fiction for Lolita in the Afterlife: On Beauty, Risk, and Reckoning with the Most Indelible and Shocking Novel of the Twentieth Century, an anthology edited by Jenny Minton Quigley. The piece is a letter from Dolores (a.k.a. Lolita) to Dear Sugar.

SB: That’s brilliant.

CS: I also wrote a screenplay about Janis Joplin—three drafts of it, in fact. It was an epic task, researching her life and then finding a way to tell her story. I was working on the screenplay when I wrote that tweet you referenced.

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?

CS: For me, whether it’s writing or anything in life, it’s important to accept that there are negative aspects of it—that parts of it are inherently hard and unpleasant and uncomfortable. We might even feel like we’re suffering. It’s like when you go to a workout class, you don’t go in thinking, I’m not going to sweat, or, This is going to be easy and I’m going to enjoy every minute of it. No, going in, you think, There 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. Writing is like that too. For me it’s important to accept that part of the way that I feel about writing, especially before I begin writing, is that I’m resistant to it, avoidant of it, and sometimes even angry that I have to do it—angry at myself for saying yes to a project or a piece. And then of course I do it and later look back on that self from a few hours or few months before and laugh because 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. I would say I’m even a step beyond acceptance of this negative aspect of writing. I now see it as a necessary part of my process. I’m not just thinking, I’ll put up with that part of me and that part of my process. It’s now more like, Oh yeah, this actually helps me do well. I need that feeling so I can do my best work.

I just had this realization a couple years ago when I was writing that Janis Joplin screenplay. I was like, This is too hard. I thought, I can’t do this. I’m going to give the money back. Just fail. And then I thought, No, I don’t want to do that. I want to push through. But I was like, What is wrong with me? Like, Why is writing so hard? I really interrogated myself to try to figure out how to cure myself of this problem. I tried to envision the place I was trying to get to.

I asked myself, What would it mean for me to change? What would Cheryl the writer be like in this new iteration without the agonizing and anxiety? And then I realized that this idealized writer I was trying to get to was insufferable. I tried to imagine myself sitting down to write and being like, I can’t wait to get started! I’m such a good writer. I’ve got this covered! Nope. I can’t write from that place of ease and confidence and enthusiasm. I have to write from that place of doubt and fear and dread. It was such an important realization because I understood that I don’t need to change. I don’t need to rid myself of that anxiety in order to continue doing the work I do. That, in fact, anxiety contributes to the work I do.

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.

CS: That’s such a wise practice. My version of what you just said is that very often when I’m feeling anxious or scared or upset about something, I’ll say, 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, Here’s my excuse why I haven’t published a memoir. Here’s an excuse why I haven’t published more personal essays, because I’ve got this fear and I’ve got these people in my life who are going to be mad at me. 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.

CS: I remember us talking about that when you interviewed me many years ago. I think that’s part of growing as a writer. Our excuses have to change over time because we realize they weren’t true.

SB: What are you working on now?

CS: I have two books in progress. I’ve written a bit of a memoir and a bit of a novel. I realize I should probably work on just one at a time, so I think it will be the memoir first. But the novel keeps interrupting me. So, we’ll see . . .

SB: I look forward to reading them both.