“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 onmy 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: Wow, it’s been ten years for both books. And nowwas just rereleased—a new edition with additional columns. Plus it’s beena stage play, and soon it will also bea Hulu showstarring 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 aDear Sugarspodcast, 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 publishingthanor?
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 onOldster Magazinecalled 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 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 . . .
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.