In the tenth addition to the Mentor Series we meet Chloe Caldwell, a writer whose career has looked quite different from the often touted “traditional” path of college, graduate school, and professorship. The author of the novella, Women, the essay collections I’ll Tell You in Person and Legs Get Led Astray, and the forthcoming memoir, The Red Zone: A Love Story, Caldwell has also taught several courses on writing for places like Catapult and LitReactor. Through those courses, she’s mentored aspiring writers like Emily J. Smith.
Emily J. Smith is a writer and the founder of Chorus, a matchmaking app where friends swipe for friends. Emily has published in the The Rumpus, Catapult, Salon, Slate, Hobart, among others, and frequently writes for Medium.
In this refreshing conversation, the two writers talk about the world of professional writing from a new perspective—one where the road to success is the one you make for yourself.
– Monet Patrice Thomas, Interviews Editor
Emily Smith: One thing I love about you and respect so much is that despite your success you’re so accessible to and real with your students—it doesn’t feel like a hierarchy but more like people learning from one another. I know mentors played a big role for you early on in your career. Is that kind of relationship with students intentional? Do you like playing that mentoring role?
Chloe Caldwell: Since I didn’t go to college, I don’t have experience in an academic setting, and that must play into the casual nature of my teaching. In high school I hated authority and being in class, sitting still, homework, so now I try to bring a different kind of energy to my classes.
Mentors have shaped my life, definitely. I do feel I had years of luck, meeting writers who meant so much to me, having them blurb my books, hiring me to nanny, helping me along, and I love that I’m now able to give back. It feels really nice to be able to use the resources I’ve created and share that knowledge with my students. Though if I’m doing too much “mentoring” I can burn out, and need to remember to have my own mentor, as well!
Smith: You’ve taken a lot of nontraditional paths, one of which is that you published most of your books without an agent. Finding an agent is so painful; there’s so much competition. And if you’re trying to sell an essay collection, I mean, forget it. (Not that I’m frustrated…) Would you recommend taking a nontraditional path like you did?
Caldwell: Often we are labeling things either traditional or nontraditional, and then thinking there are only two roads to take. But much of it actually falls in the middle. It’s funny teaching as I get older because, sort of like that line in Dazed and Confused, I keep getting older, and many of my students stay the same age. When they try to follow my path, they can’t because that path doesn’t exist anymore because it was only mine. What stays relevant though, is that to be a writer, you have to write.
Smith: Definitely things are very different now. It feels like there are infinite publications to write for these days but actually getting people’s attention from any single piece or career traction in a real way is almost impossible. It’s like the proliferation of online outlets offsets the impact of publishing in any one of them. As someone who came to writing later and definitely does not have a “typical” literary background, I’ve certainly benefited from the existence of more accessible outlets. But when an essay is published it frequently fades into the sea of content. Is your impression that things are harder or easier for new writers, now?
Caldwell: The space, I think, is harder now in a lot of ways! When I started writing personal essays, around 2007, the genre wasn’t as popular. As for taking a nontraditional path, it depends what your goals are. My goals weren’t to become rich and famous, so it worked for me, because I just wanted to write, and didn’t mind doing odd jobs to support myself. When I started writing, of course there were blogs, but there wasn’t Thought Catalog or Medium, so I feel there was less instant gratification. People didn’t get hired based on their Twitter feeds, or become famous from Instagram captions. For some reason, maybe just because I’m more immersed in it through teaching, it feels like everyone and their mother wants to have an essay collection published now, and it did not feel that way to me back in 2011.
Smith: That would be funny, if someone became a writer to be rich. You do have to love doing the work. Except, that’s not exactly it: one thing I realized when I first started writing seriously (in my thirties) was that many writers don’t actually like writing. Learning this was life-changing. I’d assumed I wasn’t a “writer” because writing for me was hard and painful and words didn’t flow out from my fingers each morning like magic. When I finally got to know other writers—like you and the people I met through your classes—I realized that’s not how it works for most writers. The difference is that writers can’t help but write, not because it’s fun or easy but because, often, it’s how they process the world. So, the struggle shifted from being a sign that I should stop to just being a part of the process.
Caldwell: Exactly. I know many writers who say they write because they failed at everything else. In Lorrie Moore’s story, “How to Become a Writer,” the first line is: “First, try to be something, anything, else.”
Smith: Let’s talk about motivation. For a long time I was ashamed that I cared so much about being read—I assumed it was just another sign that I was not a “real” writer. Then I heard Claire Messud say in an interview on the I Have to Ask podcast that she writes to communicate, and so of course she wants to be read. It was so validating, and helped me reframe my own motivations. But if you’re writing because you want to connect and communicate with people, it can be demotivating to write endlessly without knowing if you’ll ever be published. When you were first getting started, did you struggle with this? What made you keep going, keep writing?
Caldwell: It reminds me of the Winnicott quote Melissa Febos uses in her book, Abandon Me: “It is a joy to be hidden and a disaster not to be found.” I have also heard someone say that “not being read is painful” and I definitely understand that.
I didn’t struggle with motivation because I was really young, around twenty-two when I started writing seriously, and I was blind and naive and not yet bogged down by insecurity. Being so young and not having any financial expectations worked well, because then any time I got anything—like being published for no pay, or a book deal with little pay—I found it amazing. After I got something published, that would become my motivation to keep going, so I could publish something else. I struggle more with motivation now, since I am married (WTF?) and have a part-time daughter. It’s easy to just want to do family shit like watch movies and go swimming and stuff, so I find I have to encourage myself to prioritize my writing more than I used to. When I have an idea or am excited or passionate about a project, though, I’m a motivated and fast writer.
Smith: It’s true; it’s sometimes easier to be motivated when you’re young because your imagination is still grandiose and you haven’t been shackled by reality. Although maybe young is relative; I felt that naive (and still do to an extent) when I started writing even though I was in my thirties. I knew nothing about the industry—the hierarchy of literary magazines, how hard it is to get a book deal, what constitutes an “artful” essay—so I just started trying everything, writing what I wanted and publishing wherever would take me, and then began to learn the particulars over time.
Do you feel like not coming from the traditional academic path shaped how you approach writing and teaching?
Caldwell: Definitely. I’m actually grateful I didn’t do an MFA program. One of my own mentors, Carole Maso, who teaches at Brown University, also did not get an MFA and she said, “I didn’t want other people to tell me which parts of my writing mattered.” I’m paraphrasing. She said she wanted to figure that out on her own, and I feel the same way. I think teaching creative nonfiction has been my college experience, in ways. For example, I’m currently teaching an essay generator class at Catapult, online, which is a twelve-month alternative MFA program. For the program, I created my own syllabus, and a year-long reading list. In my own life, I’ve never been assigned a year-long syllabus or a reading list. So I have this brilliant opportunity to create a reading list not only for my students, but for myself. On the reading list: Vivian Gornick, Joe Brainard, Chelsea Martin, Michelle Tea, Samantha Irby, and more.
Smith: Now that you’re a few years older and have more financial expectations and less naivety, how do you stay motivated?
Caldwell: I’m probably less motivated now, because I’m not as thirsty, or at least I work slower, because now I have more responsibilities than I did when I was working as a babysitter/living at home/single/etc.
I stay motivated because I love the feeling of finishing an essay or book. And, if I don’t write for a few months, I turn into a crabby bitch.
Smith: [Laughs] It’s like the motivation to write is less about the pursuit of happiness than warding off this annoying existential itch. Do you journal or have a daily writing practice or any rules like that?
Caldwell: Nope. I know people don’t like hearing that, but it’s true. I’m more of a go-with-the-flow writer. If I’m intensely working on a project, I like it to be the first thing I do in the morning, but other than that no ritual. For me it’s just getting my ass in the chair and focusing on my project rather than reading the New York Times and online shopping.
Smith: It’s so hard. I think a lot of readers know you for your essays but you also wrote the novella, Women, and are working on a longer form project now. Do you like writing longer-form books? Do you have any preference between working on that kind of project and working on essays?
Caldwell: I love both in different ways. Essays are fun because they can be short, long, experimental, playing with tenses, and occasionally, essays are a way to break and finish something while working on a book-length project. A book-length project requires commitment of a wildly different level. With essays, when they become boring to work on, I know it will be over soon. With books, I have no idea. It could take three more years, and that thought is daunting. There’s something enjoyable though, about having a long-term relationship with a book project—the way it changes as you change, working on it in various times of your life, in an array of places. The book I’m working on now, I began when I met my partner in 2017, and now it’s 2020 and we are married, so my book-in-progress has seen me through many experiences, like a good friend.
Smith: That’s the dream. I agree with the theory that you just have to keep “showing up” for the work to come, but it’s also true—at least for me—that some days the ideas just flow and some days they really, really don’t. How does an idea for an essay or a book come for you? More specifically, what makes a story worth telling, in your mind?
Caldwell: If I find I’m telling a story over and over to my friends, that’s when I know I’ve got to write it down or turn it into an essay. The biggest thing I’ve learned from teaching is that no essays are “worth” more than others. I like to treat all my students’ stories equally—a trauma story is just as valuable as a story about being a rodent person (essay I read recently). Ideas are mysterious but one hard-and-fast rule I have for myself is if I find myself bringing up a topic repeatedly to my friends, or telling the same story over and over, it is something I need to explore on the page.
Smith: Do you consider yourself a successful writer? What does that even mean to you?
Caldwell: In the sense that I’ve been able to write and publish my books in the way I wanted to—yes. Success to me isn’t about financial gain and status. It’s having the luxury and privilege to write books while having a job I like to support me, and that keeps me in my wheelhouse of the writing world. But if success means you’re financially set and have a house “on the water” and an apartment in NYC and things are handed to you, then no! Cheryl Strayed says it best when she says that success often looks like failure to outsiders.
Photograph of Chloe Caldwell by JD Urban. Photograph of Emily J. Smith by Emily J. Smith.