CHLOE CALDWELL could easily be considered a veteran among millennial authors. Her forthright honesty and trademark “oversharing” have made her one of the most endearing and exciting writers of a generation. Her first book, Legs Get Led Astray, was published on her 26th birthday in 2012. It is a winning tapestry of candid essays that traces her stumbling path through young adulthood. Two years later, she explored her first time falling in and out of love with a woman in the widely applauded autobiographical novella, Women. Both books are poetic, intimate page-turners, and demonstrate Caldwell’s knack for slicing through the bullshit.
Her new book, I’ll Tell You in Person (Emily Books), is just as fierce, from her straight-talk on how heroin exacerbated her acne to things she hasn’t quite figured out, including her sexuality and her writing career. She’s candid about the pain of her parents’ divorce, and grateful to the myriad friends who helped her through it. “Friends in all forms. Childhood friends, Twitter friends, bad friends, fun friends, complicated friends, parental friends, mentor friends, food as a friend, drugs as a friend, attention as an addiction,” Caldwell said of those who inspired her. “Also, failure; growth.”
I’ll Tell You in Person also shows how much Caldwell’s voice has matured. While she’s divulging all her secrets, it feels less raw than before. Has age made her cautious? Or have famously unabashed women such as Lena Dunham and Amy Schumer taken some of the thunder out of her in-your-face ballsiness? Or is it simply more intimidating to let it all hang out when you know you there’s an audience waiting to get inside?
Her own feelings about the work are, at best, mixed. “I’ll Tell You in Person was like a breached baby,” she said. “The process toward publication was much more stressful than my other two books. It’s like my fucked-up kid. I look at it and think: What the hell is wrong with you? Why were you such a pain in the ass? Oh fine I love you, but you’re weird. It’s definitely harder to write when you know you have readers. I rarely thought about my readers during the writing of Women, but while writing I’ll Tell You in Person I got pretty paranoid.”
Caldwell was just as candid throughout our conversation.
ALYSSA OURSLER: Let’s start with the title. How’d you come up with it?
CHLOE CALDWELL: The title is a phrase I was texting to my friends all the time. They found it incredibly annoying. I liked annoying them. I wanted to tell them the anecdotes I was relaying face-to-face over wine, so I could speak more animatedly and use my hands and make eye contact. That sounds so creepy! I smacked the title on my manuscript and no one ever suggested a change, so it stuck.
I’ll Tell You in Person felt more grounded in time and place than your first two books. Do you agree, and was that intentional?
I do agree. Legs Get Led Astray has an urgent feel, as my material was really close to the bone as I wrote it, and Women is raw and urgent emotion, the kind of art that comes out of a painful experience. It makes sense that I’ll Tell You in Person is more grounded, because in my life I became more grounded. I gave recurring characters names and added more scenes and dialogue than in my previous books.
That said, nothing I do is usually intentional. I try not to analyze my work or purposely make something different from something else. I like to stay in a bubble of idiocy. It keeps me creative.
At what point did these essays come together as a collection, and was that process different from your first collection?
Legs Get Led Astray was just a shitshow I was working on. I was publishing essays online and then put them in a manuscript. For this, I was working on piecemeal essays for various publications. A few publishers were emailing my agent at the time — asking what I was up to post-Women — and she encouraged me to put together an essay collection. We started seeing how they’d fit together and what themes were prevalent: friendship, intimacy, identity, failure.
Is that why you decided to break up I’ll Tell You in Person into these different parts, which is something you didn’t do with your first collection?
Most essay collections are split into parts. Anne Lamott does it with most of her collections, Jonathan Ames does it, Lena Dunham did it with Not That Kind of Girl. It was a helpful way for me to wrap my head around theme: How are these essays similar and how are others different? What feel do I want to evoke? It’s not exactly a “This is how I’ve grown from childhood” memoir, so we didn’t have to use chronological order and got to play a little. The sections did have titles I kept changing in the early stages of the manuscript but over time we found them cheesy, so I nixed them.
In the intro, you write: “The liberating thing about publishing an essay collection before you are a fully formed person is that there is nothing to fear. You have no readers. No experience. No memories of doing it before. No wounds.” What were your wounds from your first collection? How have they shaped this collection?
I was probably just being dramatic.
Okay. [Laughs.] But you obviously wanted to say something specific about your love for this genre of writing? Why?
I guess because it was my third book, and I was teaching nonfiction and was sort of drowning in personal stories, my own and others. I was looking at my life and asking, “How did I get here? How am I so balls deep in nonfiction?”
Do you ever worry about reactions from the people you are writing about?
This is a question I feel we should stop asking women writers. I just read an interview with Mishka Shubaly, who writes about his life constantly. His prose was called “muscular” and “passionate.” He said his writing has ruined all of his relationships and the person interviewing him just ignored that disclosure. Since I’m a woman I get called “vulnerable,” never “muscular” or “passionate.”
If writing had impacted my life that negatively I’d probably have stopped doing it. I understand the impulse to ask me the question, but it doesn’t have anything to do with the book I wrote. I read an interview with Emma Cline recently, who said, “Asking what my parents think of my work is a way of reminding me of my social and emotional obligations as woman.”
What, then, are you hoping readers will take away from the work?
I recently had a conversation with my friend, the writer Chelsea Martin, about our essay collections, and our lack of angles and branding. I said, “I feel like my brand is just me bragging about how dumb I am,” and she said, “I just want everyone to admit they don’t understand themselves.” Ideally, everyone walks away with something different from I’ll Tell You in Person. I really like the idea of readers projecting their own lives onto it. There should be more books about women just living their lives, being human, having experiences, fucking around, and I’m honored I get to contribute to that small genre.
In the first section of the book, food is quite prominent. Then, the second part kicks off with an essay about heroin. In that progression, you really capture the way innocence and naïveté can escalate into danger. Do you think that self-awareness sets this collection apart from Legs Get Led Astray?
Probably. In Women and in Legs Get Led Astray, I’d allude to my parents’ divorce, or how I used to be into musical theater, or grew up with a bunch of guy friends, in just a fleeting sentence. In I’ll Tell You in Person, I had the space to explore those situations and themes more. I didn’t have any word count restraints, as I would if I were writing an essay for the internet, so I got to really take time and sit with sentiments I’d previously found uninteresting.
Throughout the collection, you give a lot of detail, especially with music — listing band names, citing specific song lyrics, and the like. What do you think is the key in using specifics to get to the universal?
What I love about using music is that people remember where they were when they heard a song or an artist for the first time. It brings them back to themselves, to their own home screen. I never know if I’m making the specific universal, but hopefully sometimes I do.
Most of your work centers around relationships, but I’ll Tell You in Person stands out in that it focuses far less on romantic relationships, which seem to be mentioned only tangentially. Were you done exploring romance?
I was more interested in other types of unconventional relationships I was having or had in my childhood, mentors like Cheryl Strayed and Maggie Estep, and babysitting Cheryl’s daughter Bobbi; artists I met via Twitter or through my work, like Lena Dunham, and my formative relationships with my girlfriends and guy friends. I was asking: How did I get to be the person that I am? How do we become who we are? How has relationship X from the past informed relationship Y or inspired relationship Z in the present?
Your essay “The Laziest Coming Out Story You’ve Ever Heard” is more about identity and sexuality, and, essentially, ties your three books together. Is that what you were hoping to do with the piece?
“The Laziest Coming Out Story” was born of a few anecdotes I’d forgotten to include in Women or, for whatever reason, were deleted. I like the essay because it’s never finished. Every week something happens that I could include in it. When Emily Gould [co-founder of Emily Books] sent me my editor letter before I did a new draft on the book, she said, “At times, this essay is lazy!” and I went back to it and just couldn’t make it un-lazy. Finally at the end of the editing process, my editor Ruth Curry [the other co-founder] was like, “Though this is still lazy, it’s fine. Maybe that’s the point.” I was like, “Yeah, that’s the point!”
Did you feel any pressure to include an essay about sexuality, since Women was widely considered an LGBT book?
No. I wrote “The Laziest Coming Out Story” for fun a couple of years ago and published it on Medium because I needed the money. Just because I wrote one book on sexuality doesn’t mean I’m a spokesperson for it. I guess I do feel a little pressure about it, but I don’t give into it. Women is a thing of its own and not all my books are going to be Women.
It’s funny, because Legs Get Led Astray reads pretty hetero, though one reviewer said I didn’t use pronouns in many of the essays, and another person told me they never knew if I was gay or straight in it. But I read it as a super heteronormative book. Women is kind of LGBT, and I’ll Tell You in Person has barely any sex in it at all! It’s my most sexless book to date.
I’ll Tell You in Person begins with you at age 20, without a college diploma — and you still don’t have one, even though you’re now teaching. Has this lack of “formal” writing education impacted your writing, and this collection in particular?
It impacts my writing immensely. I’m self-taught. I’m not a perfectionist. I didn’t sit through writing workshops thinking critically about writing. We submitted this collection on my 29th birthday. I was at a place in my life where I had to make some decisions. I had two books out, and no skills, really. No money. I began reflecting heavily on the choices I’d made. Like, “Well, shit. Where is there to go from here?” I either have to dive head first into my so-called career or waitress or go back to school.
Not going to college or getting an MFA means I skipped learning to be competitive. I didn’t get assaulted with people telling me I suck. I get people telling me I suck now, sure. But I’m not as vulnerable a writer as I would have been at 20. I got to stay sort of sheltered. Plus, I got to publish books with three indie presses and learn about writing and editing and publishing in this hands-on way. It was like my college.
What is your writing routine like now, and how does that compare with your routine for previous books?
I don’t have special writing routines. I work every day. Sometimes that means I’m teaching online, sometimes book edits, sometimes a new piece of writing.
My reading routines are what really vary from book to book. For Women, I read novellas as I wrote it. For this essay collection, I reread essay collections: Jonathan Ames, Joan Didion, Dodie Bellamy, Sallie Tisdale. I like immersing myself in the form I’m writing in as I work. I keep the sorts of books I’m aspiring to be like in my bed for months in case it works by osmosis.
What are you working on now?
A short story collection called Relatively Unknown. Each story will be from a different woman’s point of view, kind of like Personal Velocity by Rebecca Miller. I’m also dabbling in Final Draft, thinking about taking my shot at a screenplay.
You talk about five-year plans in the book, and laugh about them. But you also grow up a lot throughout the book. Do you have one now?
Nah. It makes me uncomfortable to think about my life in that way.
What’s been the most unexpected thing about your writing career?
Teaching. Never in a billion years would I have expected I’d be helping people with their writing or making my income this way. It’s so challenging, constantly changing, and exciting. I now have dozens of interesting women in my life whom I met in my classes. It’s unbelievable. And I get to work from home most days a week. I feel so lucky.
What advice do you have to other writers of personal essays?
Change names and/or let your friends choose their pseudonyms. Don’t ask for permission, but do warn people. Never surprise those in your life with an essay you haven’t given them a warning about. Sit with the essay longer than you think you have to. And always write with love.