Cheryl Strayed’s Dear Sugar

Hello friends!

It’s time for another installment of my occasional Tells Us series, in which I ask an author to tell us about five things. I know I often say something along the lines of “and this one is extra special,” but this one…really is extra special because it’s Chloé Caldwell who, from pretty much the moment I met her, has felt like family to me.

Chloé and I met at a party in Portland in 2011 on my 43rd birthday, when she was 25, but we’d been corresponding online for several months before that, after she’d read and tweeted about an essay I’d published nine years before called “The Love of My Life.” Shortly after we got to chatting, we discovered that when the essay was originally published in The Sun magazine, Chloé’s mom, Michele, had read it and written to me—saying things that her then-teenaged daughter would echo years later—and Michele and I also discussed our mutual love for Lucinda Williams. Chloé was gobsmacked by this and in her email to me she wrote: “I guess I am more like my mother than I thought.”

Which always makes me laugh because, girl, DUH.

Ever since then, I’ve rooted for Chloé the way one roots for their favorite wild niece. It’s been an exquisite pleasure to watch her do exactly what she said she was going to do and make a life of writing, as an author and teacher. Her books are intimate and honest, edgy and bold, tender and searching. When I have a book she’s written in my hands, I never want to put it down. It always feels like a box of secrets you get to open.

Her new book is Trying. It’s a memoir about her efforts to become pregnant and her deep desire to have a baby and also about her life falling apart suddenly. (Spoiler alert: she puts it back together, better than before.) I read it in a couple of big gulps, staying up too damn late to finish it. Afterwards, I lie in bed wondering if I should text her to say how much I loved it, but decided to wait until morning, since it was the middle of the night in her time zone. When I picked up my phone the next morning there was a text from Chloé telling me she loved me and she was grateful for the years of our friendship in its “many stages and colors.”

I am too, Chloé. Happy pub day!

xCheryl

Tell us about a time when you took advice that turned out to be really good or really bad.

My dad passed away last December, and he was in the top three closest people to me over my life. He used to have a phrase he used with his guitar students: “You get good at what you do. If you practice guitar, you get really good at guitar. If you don’t practice, you get really good at not practicing.”

I love this phrase because you can apply it to every single thing in life, in ways both literal and abstract. If you write, you get good at writing If you look at Instagram, you get good at looking at Instagram. If you walk, you get good at walking. If you swim, you get good at swimming. If you write, you get good at writing. If you don’t write, you get really good at not writing. If you look at Instagram, you get REALLY good at looking at Instagram.

I think my dad’s lesson seeped into my brain from hearing him say it so much. It wasn’t advice as much as a notion. Now I pass it along to my students and think about it once a day. It seems simple and like something we all know, logically, but the way it is phrased really drives it home.

When he died, one of his guitar students wrote, “Rob was good at love and music. It’s what he did.”

There are so many more nuggets of advice I’ve gleaned from people, one of those people is, you, Cheryl. Once you (she?) told me your friends remember if you go to your wedding or not, and I’ve applied this to friends’ book launches and other big live events. I’m definitely not always there! But I do my best to put in the effort because I think you’re right that people remember. You don’t have to do anything drastic, just make an appearance. Also, “Your book has a birthday, you don’t know what it is yet” — that ran through my head again and again in my twenties. I definitely attended the School of Cheryl Strayed.

I suppose the above is not advice either; it’s also a notion. Apparently I gravitate toward notions, philosophies, and nuggets rather than advice. Interesting.

Actual advice: my mom always said to put sunscreen on your hands to protect them from sunspots. Another one from my dad: Lean forward and roll down the hill. When I asked him what it meant, he said, “Make a decision and don’t think, just act.” Advice from Lidia Yuknavitch: “collect rocks.” My uncle once said “pay yourself first” meaning put some of what you get paid into a savings account. It stuck.

There are some notions I loved in a class I once took with Sheila Heti, one being “You are your own authority.” She meant of your book project, and it resonated so deeply with me. She explained no one is above you, no teacher or mentor or professor or workshop class mate. You get to choose. There is something really powerful about creative agency.

Tell us about a personal transformation in your life or a change that you’ve made for the better.

In May 2023 I left my marriage, once the way I was being deceived came to light. I wasn’t really conflicted on the decision.

Once I left, so much in my life improved — some immediate and some over time. It was as though the clouds parted and the sky broke open. My writing became a big focus, the way it had been in my twenties. Financially, I began thriving more than I had. Spiritually, I felt lighter and more connected to the world and everyone around me. It showed me—quickly—because life changed quickly—what and who my resources were. It came to light how many inner resources I’d built within myself. Some people fell away, and the real ones came into focus. It clarified my friendships. And finally, I could write. No matter how uncertain other aspects of my life had gotten, no one could take that away from me.

Even though I’d sold my book under one premise (notes on desire and unexplained infertility) I allowed it to morph into another book about disenfranchised grief and queer reawakening. The whole experience made me trust my intuition in an intense way.

Tell us about your new book, TRYING.

Yikes. Trying is maybe the book I’ve been writing toward for a while now. I’ve published four books of nonfiction and autofiction, and never had this experience where my life blew up while writing the book. When I sold the book in March 2023, it was a book of notes observing the fertility industrial complex, yearning to get pregnant. In May 2023 everything changed and my life as I knew it was over. A more honest, queer, and authentic life was waiting in the wings. From there, I continued writing my book in real time, because it was all I could do. I kept the first section of the book true to how I’d written it, and over time, with support from my editor, Yuka Igarashi at Graywolf, figured out how to approach what would become Act 3, which actually doesn’t come at the end but comes halfway through the book. In Act 3, the structure and tone and voice changes, because in life, my structure and tone and voice changed. Yuka and I have described it as the book going from black and white and into color. Suddenly, the book becomes loose and fast and unhinged the way my life did. I ended up having a spiritual experience writing the book, learning my body and subconscious knew something my surface-brain did not. It was powerful and made me love writing all the more. There’s a line in the book, “I love writing.”

It’s a book that’s perfect to give divorced and gay friends, or anyone who thought they were living one life and ended up living another.

Tell us about a regret you have or a mistake you’ve made.

It’s wild how this stumps me, even though I’ve made massive mistakes. My dad used to roast me saying the alternate title for one of my essay collections was “Feel Bad For Me: I Fucked Up 28 Times and I’m About To Do It Again.” He said this lovingly, of course!

I definitely regret the times I didn’t live with integrity or authenticity, but without those times I wouldn’t know what integrity or authenticity feels like, so I don’t fully regret those either.

I have some silly meaningless tattoos, sometimes I consider getting rid of them. There are many instances I could have been a better friend, communicated better, been less reactive. I don’t think I needed to get married. But again, I don’t regret that stuff, because it led me here, and I like my life. Writing has been a huge reason why.

Tell us your best advice.

Make art and writing. I am obsessed with something I read once about how writing strengthens the immune system. I think that’s fascinating. It doesn’t matter if people read or see your art, but if you feel the need to make / write something, the worst thing you can do for humanity is to not honor that. Art and writing heal and connect us. I’m unclear how people survive without it.

Be clear and direct. Clarity is underrated.

Use your resources. I love this one because it can (like “you get good at what you do”) be applied to anything. You can apply it to creativity, community, and your town. You can apply it to your friends with skills, your mentors you’ve fallen out of touch with, your local library. It can be something as small as your pantry and something as large as New York City. I use this phrase / concept for everything and it’s lowkey life-changing.

CHLOÉ CALDWELL is the author of the national bestseller, Women (Harper Perennial, 2024). She is also the author of the books I’ll Tell You In Person, The Red Zone, and Legs Get Led Astray. Her essays have appeared in The New York Times, Vogue, The Believer, Bon Appétit, The Cut, Vice, Longreads, Nylon, The Rumpus, and half a dozen anthologies including Goodbye To All That: Writers on Loving and Leaving NYC and Without A Net: The Female Experience of Growing Up Working Class, and Sluts. Chloé lives in Hudson, New York. She offers writing support at www.scrappyliterary.com and on her Substack.