The Memoir Land Author Questionnaire #128: Chloé Caldwell
"Over a year after working on the book, and a few months after selling it, my life blew up overnight so I had to figure out what the concept of 'trying' was going to be post-divorce."
Since 2010, in various publications, I’ve interviewed authors—mostly memoirists—about aspects of writing and publishing. Initially I did this for my own edification, as someone who was struggling to find the courage and support to write and publish my memoir. I’m still curious about other authors’ experiences, and I know many of you are, too. So, inspired by the popularity of The Oldster Magazine Questionnaire, I’ve launched The Memoir Land Author Questionnaire.
Here’s the 128th installment, featuring serial memoirist Chloé Caldwell, author, most recently of Trying: A Memoir, out last week from Graywolf Press. - Sari Botton
P.S. Check out all the interviews in The Memoir Land Author Questionnaire series.
CHLOÉ CALDWELL is the author of the national bestseller, Women. 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, Bon Appétit, The Cut, Vice, The Believer, Nylon, The Rumpus, The Sun, 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. She offers writing support at www.scrappyliterary.com. Her substack is at chloecaldwell.substack.com. She lives in Hudson, NY.
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How old are you, and for how long have you been writing?
39, writing for twenty years. I never went to college or got an MFA but began taking my writing seriously around 23.
What’s the title of your latest book, and when was it published?
Trying, published on 8/5/25 by Graywolf Press.
What number book is this for you?
Five.
How do you categorize your book—as a memoir, memoir-in-essays, essay collection, creative nonfiction, graphic memoir, autofiction—and why?
I’d categorize it as an experimental memoir. It’s definitely creative nonfiction and heavy on the stylistic choices. Since it is with an independent press that pushes outside-the-box books, I felt I was able to be a bit free with it.
During first (and second, and third) drafts, I live by Sheila Heti’s writing advice of, “You shouldn’t know what you’re doing or why.” I love not knowing how I’m going to end a book. Something else surprising is how readers make connections and notice stuff in my books that I don't. I write a lot on instinct and intuition, so the work makes organic connections, and sometimes they’re there subconsciously. It’s a really fascinating experience.
What is the “elevator pitch” for your book?
The book is for anyone who thought they were living one life, but ended up living another. It is for anyone whose life has blown up, or might blow up. Or if you are considering blowing it up. It could be a gift for a recent (or longtime!) divorced or separated person, someone having a queer awakening or reawakening, and for anyone that wants to write / make a lift of writing and creativity.
What’s the back story of this book including your origin story as a writer? How did you become a writer, and how did this book come to be?
I became a writer through writing all the time. When I was working on this book, I reached out to my past editor at Soft Skull, and asked if she would be at all interested in seeing the material. For the next year, I sent her material a few more times with some feedback she gave me. I worked on deepening the material and pushing it further. In March 2023, I sold it to Graywolf.
What were the hardest aspects of writing this book and getting it published?
This process was insanity. Even though I’ve written four other works of nonfiction and autofiction I’ve never had this experience before. I sold the book under the premise of unrequited desire and trying to get pregnant—I wanted to offer a narrative that didn’t end with IVF or a baby.
However, over a year after working on the book, and a few months after selling it, my life blew up overnight so I had to figure out what the concept of “trying” was going to be post-divorce. My editor gave me some space and collaborative support while we did some trial and error as to what the book was going to turn into. I felt and feel lucky to have had my book by my side while everything else was so uncertain.
The book is for anyone who thought they were living one life, but ended up living another. It is for anyone whose life has blown up, or might blow up. Or if you are considering blowing it up. It could be a gift for a recent (or longtime!) divorced or separated person, someone having a queer awakening or reawakening, and for anyone that wants to write / make a lift of writing and creativity.
How did you handle writing about real people in your life? Did you use real or changed names and identifying details? Did you run passages or the whole book by people who appear in the narrative? Did you make changes they requested?
I think like with anything, you use your own ethics. Every relationship and friendship is different. Unfortunately, there is not one size that fits all. I changed some names and kept others.
No, I did not run passages by anyone.
Who is another writer you took inspiration from in producing this book? Was it a specific book, or their whole body of work? (Can be more than one writer or book.)
Notes To Self by Emilie Pine, Little Labors by Rivka Galchen, Notes To Myself by Hugh Prather, Knocking Myself Up by Michelle Tea, In Vitro: On Longing and Transformation by Isabel Zapata.
What advice would you give to aspiring writers looking to publish a book like yours, who are maybe afraid, or intimidated by the process?
When people have a desire to write or make art, they should do it, because it makes people happier. The publishing industry is definitely challenging, gatekeeper-y, and hierarchical in many ways. That is why I launched Scrappy Literary, to demystify publishing as well as heal people from MFA culture.
One thing I’d say is that you don’t have to throw thousands of dollars at writing. The library is free, as is typing.
What do you love about writing?
Freedom.
What frustrates you about writing?
Underpaid.
I’d categorize Trying as an experimental memoir. It’s definitely creative nonfiction and heavy on the stylistic choices. Since it is with an independent press that pushes outside-the-box books, I felt I was able to be a bit free with it.
What about writing surprises you?
Everything. During first (and second, and third) drafts, I live by Sheila Heti’s writing advice of, “You shouldn’t know what you’re doing or why.” I love not knowing how I’m going to end a book. Something else surprising is how readers make connections and notice stuff in my books that I don't. I write a lot on instinct and intuition, so the work makes organic connections, and sometimes they’re there subconsciously. It’s a really fascinating experience.
Does your writing practice involve any kind of routine, or writing at specific times?
Like many writers, I love mornings and caffeine. Unlike many writers, I listen to music with lyrics all day while I’m writing. I like to light a candle just to signify the start of the process; I find it soothing.
Do you engage in any other creative pursuits, professionally or for fun? Are there non-writing activities do you consider to be “writing” or supportive of your process?
I’m of the philosophy that everything is writing. Reading, swimming, walking, yoga, obsessing. Resting. Music. Talking with friends. Sleeping and dreaming.
What’s next for you? Do you have another book planned, or in the works?
I’ve been working on a top secret novel for over two years. I’m also hosting an accountability group through Scrappy Literary and I’ll be hosting a retreat called Writing Chaos In Real Time in the near-ish future.
I thoroughly enjoyed this interview and thank you for it! I read Women last year, and it immediately went on my "inspiration" shelf. I had no idea Caldwell didn't have an MFA, which is encouraging as a fellow writer without an MFA who started taking writing seriously around 23. Can't wait to get my hands on a copy of Trying, and will look into Scrappy Literary!
Excellent interview! #proudaunt of CC!