Chloe Caldwell’s first two books, the essay collection Legs Get Led Astray and novella Women, built up an almost-cultish audience of devoted readers who return to her books the way fans of a band play favorite albums on repeat. The music analogy is deliberate, as Caldwell’s writing is heavily infused with references to music. The title of her first essay collection is a lyric from the Okkervil River song, “Last Love Song For Now,” and her new collection, I’ll Tell You In Person (Coffee House Press/Emily Books, October 4), begins with an epigraph from David Berman, the lead singer of the Silver Jews. It’s hard to read more than a few pages of Caldwell’s writing without hearing one of the songs she mentions play in your head, if you’re lucky enough to know that song. Over email, I asked her a series of questions about how music works in her writing and life.

—Andrew Bomback for Guernica

Guernica: One of the things I love about the way you use music in your writing is that you don’t dumb it down for your audience. You reference bands and songs that may not be familiar to readers, often without explanatory details. How do you imagine your readers processing these lesser known music references in your writing?

Chloe Caldwell: I don’t feel the need to educate people with a parenthetical aside like “Great song by the way!” How obnoxious that would be. I never thought about people learning about new music from my books, but if they do, that’s great. Music is such a huge part of my life that it’s obvious it would sneak into my writing in a casual way.

I’m not trying to choose obscure songs. Recently my mom said, “You write about me so much!” after she read a galley of my new book. It’s the same with music as with my mom: since my books are first-person narratives, it makes sense songs would sneak in. And I’m writing exactly what I listened to, so I never have the option of using a less obscure song. You are what you listen to.

Guernica: When you’re drafting, do you have a song playing in the background so that your memory is as accurate as possible?

Chloe Caldwell: I usually do not try to make my memory as accurate as possible and listen to the songs I am writing about while writing. What I will do, though, is choose songs or albums that evoke a specific feeling. I wrote Women to the same three songs for a year: “I Follow Rivers” by Lykke Li, “Pink Rabbits” by The National, and “Devon” by Grimes. All break-up songs. I wanted the book to stay in that tone of heartache, and those songs helped me access it. Many of my writer friends can’t listen to music with lyrics while writing, but it doesn’t bother me at all.

The one time I did use music to trigger memory accuracy was for I’ll Tell You In Person (ITYIP). I was encouraged by an editor to write about my parents’ divorce, and I knew I had to do it through music and how music was an escape for me as a teenager. So I wrote the essay “Music and the Boys” and got to indulge in a bunch of ’90s and early 2000s music. I even made a Spotify playlist for it, but some of those songs are so bad I didn’t end up listening to it much.

One thing I stopped doing while writing about music (at least, mostly) is including a bunch of song lyrics. That was a habit for me, and I don’t think it’s effective. It’s trying to get the reader to see why the song was so important to you, and it rarely works well. Most people don’t want to read half a page of italicized song lyrics. So often I still put lyrics into my first drafts but cut them later.

I didn’t like that “singing” was something someone could command you to do, and when you said no, you were a dick.

Guernica: In the new collection’s essay “Failing Singing” you write about singing during your childhood and teenage years. How much has your singing background prepared you for the intimacy required in writing a personal essay? How does the experience of being exposed onstage compare to the experience of being exposed on the page?

Chloe Caldwell: In that essay I am trying to figure out (and I don’t, not really) why I became so turned off by singing, and what I’ve concluded is that it made me feel too vulnerable. I didn’t like that “singing” was something someone could command you to do, and when you said no, you were a dick.

With writing personal material, at least you can take a long time to decide what to expose, right? You don’t have to do readings, and people can still access what you’ve made—your books. Singing in front of people is like, if you flub, you’re fucked. It’s like writing an essay on the spot. This is why I’m so enamored with people who do stand-up comedy and storytelling series. I suppose I’m terrified of the immediacy of the form.

After a singing recital, people are judging how well you did in that moment on that day, five minutes ago. With readings, they are judging something you wrote a year ago, or five years ago, a finished project, unless you’re one of those writers who works out their material during readings and reads from works-in-progress. I’d be scared to do that.

Guernica: Do you ever think about how you’ll eventually read or perform an essay when drafting?

Chloe Caldwell: I never think about doing readings while drafting, to the extent that about three times in the past couple months I’ve had the fleeting thought of, “Fuck! I’m gonna have to do readings from this book! What the hell am I going to read?” It feels like that each time with a new book, though. You can’t imagine reading from it. Then a year goes by, and you can’t imagine not reading from it. But I do think standing at a microphone (this singing essay was originally titled “Microphones”) was a skill I learned through my teens, to stand and perform—and that even though I was nervous, I never peed my pants or had an anxiety attack.

The thing I liked about musicals and choosing/learning songs to sing in my voice lessons and recitals was that the songs told stories. And I’ve always noticed some of my favorite songs are like personal essays. They tell stories; they begin us in one place and end us in another. “Stone” by Okkervil River: personal essay. “The Art Teacher” by Rufus Wainwright: personal essay. “The Opposite of Hallelujah” by Jens Lekman: personal essay. Any song by Joanna Newsom: experimental personal essay. I like songs that have tiny mundane and concrete details like the ones I enjoy putting into my essays.

Something I forgot to mention in “Failing Singing” (goddammit) is that once, after practicing singing to various songs and musicals while my dad was home, I asked him how I did. He said something to the effect that I sounded great but that I was mimicking exactly what I was hearing. I could sort of change my voice to sound like everyone else’s. I never found my own voice singing as I did with writing.

Guernica: I like your analysis of songs as personal essays. Which artists/bands do you think align with your writing and which specific songs (besides the ones mentioned above) specifically sound like a Chloe Caldwell essay?

Chloe Caldwell: There are musicians I haven’t necessarily mentioned in my books who, I feel, are doing what my essays would do if they were songs. I would hope so. Their names are: Sharon Van Etten, Claire Boucher (Grimes), Lykke Li, Camille, Soko, Ane Brun, Natalie Prass, Marisa Nadler, Frida Hyvönen, Mitski, Emmy The Great, Angel Olsen, Lady Lamb, and Mirah. These women are around my age, and I’ve read interviews with them, and we write about similar themes: coming of age, feminism, heartbreak, solitude, ambition, therapy (see Sharon Van Etten’s song, “You Know Me Well”), and sexuality. Marisa Nadler even has a song titled “Hungry Is the Ghost” on her new album, about which I had no idea when I wrote my essay “Hungry Ghost” for ITYIP. Then there’s Courtney Barnett who does the stream-of-consciousness thing in her songs I do in my essays, particularly her song “Depreston.” Oh, and Bethany Cosentino of Best Coast, of course! I love her upfront take on moods and hormones and depression and financial/career struggles. She wrote an excellent essay for Lenny Letter, too!

Guernica: In “Music and The Boys,” as you mentioned, you weave in a number of hit songs from the 1990s and 2000s and even include a Beyonce song at the end. The essay feels more “mainstream” than some of your other work, particularly because of the music choices (e.g., Soul Asylum, Macy Gray). Is there a different level of pressure, or expectation, when writing about popular songs that everyone knows and about which everyone has their own distinct memories and feelings?

Chloe Caldwell: Ah, so that’s why a friend told me I should publish that essay in Seventeen magazine! It makes sense: “Music and The Boys” would feel more mainstream since it takes place in high school, so there was a need to fit in, to be the same as everyone, to like the music the boys liked, even if I didn’t like it (but I did). I was the person in my family who liked mainstream music and radio. Then, after high school, when my brother caught me listening to Jack Johnson for a year (he’d gotten into my car twice in one year, and I still had “Brushfire Fairytales” in my CD player) and he gently told me it sort of sucked, he gave me the Elliott Smith CD “Either/Or,” which I loved, and then he continued to give me more obscure music. I remember sometimes I’d have something weird like CocoRosie playing in my car and would switch it out with something more mainstream if a friend was coming into my car. Like I hid the part of myself that liked good music.

I also enjoy when someone close to me wants to recommend me a song and they’re like, “I think you’ll like it—I’m not sure,” as though I am unpredictable in my taste, because I am.

But in writing about that time, I don’t feel a different level of pressure. My editor, while we worked on that essay, said, “We really don’t know how you feel about this frankly terrible music.” So I added in at one point that I was embarrassed. I didn’t want to add that, though. I felt some loyalty toward the frankly terrible music. I didn’t want to make fun of it, because we loved that music at the time. We didn’t know not to. There’s a sweet innocence to that, to thinking Shakira is the shit.

Guernica: The music critic Ben Ratliff has described how a listener can become a “proprietary shareholder” in the music he or she hears. We become “One Who Likes Song X” or “One Who Likes Musician X” or even “One Who Wants to Own All of Musician X’s music.” The proprietary shareholder listens to music with a “vertical sensibility, following a single line through time.” Do you agree with Ratliff’s shareholder ideas when it comes to music? And do you think it applies to books, yours in particular?

Chloe Caldwell: I do agree. I have this problem where sometimes I think I own works of art: I do this with music, movies, certain essays. In ITYIP, I mention this habit and the concept of participation mystique, not knowing where you begin and the artist ends. I suppose I do that with the musicians I listed in your previous question.

In my early twenties, I was a very aggressive music listener. If I drank too much, I’d go behind the bar and change a song on the bartender’s iPod. So not only did I identify with what I was listening to, I made other people watch me do it. So it became my “brand” of sorts. Then I went further and sprinkled the songs and bands in my writing, calling Legs Get Led Astray after an Okkervil River lyric, making it my brand even further just to get Will Sheff’s attention (which has not yet worked).

I love being “One Who Likes Song X.” I remember once, when I was living in Seattle, I had a voicemail from my dad and brother and they were like, “We’re listening to ‘You Broke My Heart’ by Lavender Diamond talking about how you love it.” I also enjoy when someone close to me wants to recommend me a song and they’re like, “I think you’ll like it—I’m not sure,” as though I am unpredictable in my taste, because I am.

I’d hope my books are okay on their own, but I certainly love following writers’ trajectories and development over time. Something cool that could happen is if a reader hasn’t heard of me and reads ITYIP, then goes back to my previous works, the way we do with albums. That recently happened to me with St. Vincent. I hadn’t heard of her. Then she was very popular, so I listened to her newest release but realized I like her 2011 album the most. It can be fun to do that, to read and listen backwards.