There is a time in every avid reader's life when books play the part of the best friend. Or, at least, there was a time in this avid reader's life when books were her best friend. My favorite books served several of the same roles that IRL friends did; the voices that came out of my most dog-eared pages made me laugh and cry, taught me things about the people around me and about myself; they kept me company on nights I couldn't sleep and were what I turned toward when I needed reassurance that I was not alone in this world—or, at least, that I wouldn't be forever. It was in these books that I found a reflection of myself and my experiences, even if that reflection wasn't crystal clear; the distortion sometimes even made it easier to connect.
A book doesn't have to feel like a friend for me to love it, but it is this type of book that I am likely to read over and over again; it's this type of book whose pages I fill with marginalia, whose underlined passages I text to everyone I know, whose sentences resonate as much—or more—in my head as do those in conversations I have over the course of a day. And Chloe Caldwell's latest, a collection of essays titled I'll Tell You in Person, is one such book; it will stay with you in its messy, funny, bitter, poignant, ecstatic, tragic wholeness while you read it and long after, as if it were a person you met at a party, one who you want to see again and again.
Caldwell, whose previous works include the novella Women and the essay collection Legs Get Led Astray, has an uncanny gift for engaging her readers on a level of intimacy usually felt only between people who know one another in reality. Perhaps this is because Caldwell exposes the parts of her life that so many young women tend to keep hidden, that so many young women are told are too private for public consumption, the very definition of the overshare. But, of course, refusing to name or speak about something doesn't take away its power, and Caldwell's essays prove this by illuminating problems both mundane and extraordinary, granting readers the ability to confront the things that trouble them in their own lives.
This is a powerful thing, but its importance does not weigh down Caldwell's work; the fact that she covers weighty topics in some of her essays does not detract from the overall lightness of this collection. In fact, there is an airiness, a breathability to Caldwell's writing, maybe because reading it feels like she is talking to you, in one long, beautifully constructed burst, and so the selections in this book feel correspondingly like a conversation, rather than a lecture. There's a throughline of wit and a hyper-attuned awareness of the absurdity of some of the situations Caldwell finds herself in, ones that are recognizable to any woman who's been in her 20s, but also distinct to the author (and distinctly funny—after reading "Hungry Ghost," you will have a hard time not cracking yourself up thinking about candle shopping at T.J. Maxx). In short, ITYIP is the type of book that is tempting to describe as a bible for young women, but which, since it lacks any pomposity or self-seriousness, evades that type of classification. Rather, it feels more like a beautifully written set of field notes, a journal from the front lines of being a young woman, the kind of book that is impossible not to respond to and not to want to press into the hands of all your best friends, the ones that aren't books.
Below, Caldwell explains how "intimacy is sort of her thing," what makes something worth writing about for her, and how it's stupid to think that successful writers need to live in New York City.
The title of this collection really struck me, I think because it speaks to an intimacy that can be difficult to experience in this era of texting and canceled plans. I feel like I tend to hoard my best stories to tell to friends and family on the chances I get to actually see them, rather than via phone or email. Were you aiming for this level of intimacy when writing these?
Yes—I hoard my stories too! Then, when I find I’m telling the same story over and over, like I did with "Hungry Ghost," I know I need to make it into an essay. I’m always aiming for intimacy in my work, it’s sort of my thing. With my novella Women, though written in a really intimate voice, I was vague. The narrator had no name, no age, worked at an unspecified library, and never named a city. That was fun for me, and I purposely did that so the reader could envelop themself in the experience and project onto it. One girl asked me if it was about NYC, another thought it was set in San Francisco.
With ITYIP, since they were personal essays, I had to get more detailed, giving names and locations to ground the reader in place and time. I love tiny nuanced details. I do realize they alienate some people, but it doesn’t matter to me.
You cover a lot of ground in these essays, touching on topics ranging from the death of a close friend to acne and heroin problems to babysitting to preparing for the visit of a (famous) internet friend to what it was like to come out as queer. Some of the essays center around objectively big, life-changing events, whereas others are about smaller moments, the kind of things some people might not think to write about. What makes something worthy of writing about for you?
There’s no criteria for me. The more interviews I do and questions I am asked, the more I realize how laid-back I am. I honestly do what I want. I keep writing [what's] enjoyable for myself. I will never force myself to write something and I never tell myself “who cares that’s boring.” Some of the essays, like "Soul Killer," of course everyone responds to because of the content, and then there is "Failing Singing," which is about, like, nothing, and inspired by Meghan Daum’s Music Is My Bag. I guess I wanted to challenge myself to take something mundane, like my relationship and singing, and see what I could make of it. Internal conflict is often the basis for my essays.
Personal essays are having a real moment, enjoying both positive and negative attention. Why do you think they—specifically ones written by women—are such current cultural lightning rods?
I think women are hungry to hear the experiences of other women in literature and film. And we’re lacking them. Just look at the success of Jill Soloway or Cheryl Strayed—though they’d been working towards it for decades. They dared to tell stories from their experience and point of view, through the female gaze, and people are responding. We need more women to do this!
What is it like to write about people that are still in your lives? Your family members and friends play prominent roles in many of these stories, and one famous friend—whom you leave anonymous, but who is relatively identifiable—has a story based around her; what's it like for you to write so honestly about these relationships? Have you ever experienced any blowback? Or, the opposite? Has it strengthened ties?
This question is asked to me in almost every interview, and you’re the first to ask me if it has strengthened ties. Yes, it has. I’m working on an essay either called "In Defense of the Parents of Writers" or "On Shame and Shamelessness" about this question. I feel like many times I’m asked, the person is implying that I am doing something wrong or bad. I’m not, and my family and friends know I write because I’m a writer—not to expose anyone or stir the pot. I researched interviews with male writers like Jonathan Ames, Mishka Shubaly, and Daniel Nester to see how often they are asked these types of questions, and barely found anything.
I spoke to Lena [Dunham] about the essay I wrote about her ["Hungry Ghost"]. I never blindsided anyone; I always warn them ahead of publication. She read Hungry Ghost before the book published. She was supportive. She said she trusted me completely. I made sure I was the one who looked like the idiot in the essay. The essay is truly for me, mostly about making internet "friends" and money and class.
You've written both non-fiction and fiction, with your excellent novella Women. Which comes easier for you? Are you working on any more fiction?
Women was more enjoyable to write than ITYIP. I love using white space the way I did in the novella; there’s more room for experimentation. I do have some exciting news to announce about another book of fiction, but the contract is still in the works so that’s all I’ll say.
Recently, there's been some conflicting takes about whether or not writing is "a job," and, if it is "a job," whether or not it's one off of which people can make a living. As someone who writes, but also teaches and who has written about money—and lack of it—in a highly relatable way, what's your feeling about the current state of writing as profession? Is it tenable to expect to be able to make money solely as a writer? Or is it necessarily a bad thing if writers have other sources of income, out of need or even desire?
I survive as a writer by teaching writing. This is huge for me, as I didn’t study writing myself or go to college. I’m hanging on by a financial thread, and to do that, I have to teach three classes at a time, host private workshops at my apartment, work for a catering company, and, once in a while, work at my dad’s music shop. I make chunks of money from writing or book advances once in a while, but not enough to live on.
A lot of writers feel like they need to live in New York City in order to be part of the larger publishing scene. What's it like for you to be a working writer and not living in New York?
Do people still think that? Seems stupid. There’s no time to write in NYC. Everyone is at their job 40 hours a week or commuting to their job. I love living in Hudson because my bank, post office, and therapist are all a two-minute walk away. It saves me so much time. I’ve lived all over the place, running to buses and trains, writing during my work time, so I love being settled and I love working from home and having a nicer apartment than I’d ever have in NYC. Plus, I’m in NYC once a week, sometimes more, for teaching and events, so I get my fix that way. Personally, I’d love to read more books and see more movies NOT set in NYC.
Do you have any advice for young women writers who aren't sure how to begin their careers?
Make friends with other writers. Go to events, book parties, classes, readings. Support the writers you love and they will support you back. Read everything. Use Twitter to make friends. Many women have been asking me how to find a mentor. They will find you, but they can’t find you without you taking some risks. Put yourself and your work out there, so you can be found. Don’t wait for anyone else's permission to write.
What have you read lately that you've really enjoyed?
I loved When Watched by Leopoldine Core. It's an incredible work of art of short stories, each inserts you into the point of view of a different character experiencing their relationship. Right now I’m enjoying a novel called Plastic Vodka Bottle Sleepover by Mila Jaroniec, which will be released mid-November.
I'll Tell You in Person is now available for purchase here.