The Mentor Series: Emily J. Smith and Chloe Caldwell

Learning this was life-changing. Smith: [Laughs] It’s like the motivation to write is less about the pursuit of happiness than warding off this annoying existential itch. Smith: Definitely things are very different now. (Not that I’m frustrated…) Would you recommend taking a nontraditional path like you did? I stay motivated because I love the feeling of finishing an essay or book. 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: That’s the dream. For example, I’m currently teaching an essay generator class at Catapult, online, which is a twelve-month alternative MFA program. Emily J. 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. Smith. 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. Success to me isn’t about financial gain and status. 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. Caldwell: I love both in different ways. More from this author → 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. 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. 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. 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. Caldwell: Often we are labeling things either traditional or nontraditional, and then thinking there are only two roads to take. A book-length project requires commitment of a wildly different level. I know people don’t like hearing that, but it’s true. 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. I struggle more with motivation now, since I am married (WTF?) and have a part-time daughter. More specifically, what makes a story worth telling, in your mind? 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. But when an essay is published it frequently fades into the sea of content. – 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. Caldwell: Definitely. 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. On the reading list: Vivian Gornick, Joe Brainard, Chelsea Martin, Michelle Tea, Samantha Irby, and more. 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. It feels really nice to be able to use the resources I’ve created and share that knowledge with my students. Through those courses, she’s mentored aspiring writers like Emily J. 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. 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. It was so validating, and helped me reframe my own motivations. Smith: It’s so hard. Smith: You’ve taken a lot of nontraditional paths, one of which is that you published most of your books without an agent. Caldwell: Nope. 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. For the program, I created my own syllabus, and a year-long reading list. What made you keep going, keep writing? I’m more of a go-with-the-flow 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. I think teaching creative nonfiction has been my college experience, in ways. I’m actually grateful I didn’t do an MFA program. Caldwell: Exactly. So I have this brilliant opportunity to create a reading list not only for my students, but for myself. Smith: Now that you’re a few years older and have more financial expectations and less naivety, how do you stay motivated? The Mentor Series: Emily J. I know many writers who say they write because they failed at everything else. 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). 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. Cheryl Strayed says it best when she says that success often looks like failure to outsiders. 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. Is that kind of relationship with students intentional? 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. 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. People didn’t get hired based on their Twitter feeds, or become famous from Instagram captions. Though if I’m doing too much “mentoring” I can burn out, and need to remember to have my own mentor, as well! 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. She said she wanted to figure that out on her own, and I feel the same way. When you were first getting started, did you struggle with this? Photograph of Emily J. It’s like the proliferation of online outlets offsets the impact of publishing in any one of them. I know mentors played a big role for you early on in your career. 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. In my own life, I’ve never been assigned a year-long syllabus or a reading list. 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. But much of it actually falls in the middle. 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. And if you’re trying to sell an essay collection, I mean, forget it. After I got something published, that would become my motivation to keep going, so I could publish something else. Share this:Click to share on Facebook (Opens in new window)Click to share on Twitter (Opens in new window)Click to share on Tumblr (Opens in new window)

Emily J. Caldwell: The space, I think, is harder now in a lot of ways! Do you feel like not coming from the traditional academic path shaped how you approach writing and teaching? Finding an agent is so painful; there’s so much competition. Smith is a writer and the founder of Chorus, a matchmaking app where friends swipe for friends. 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. When I started writing personal essays, around 2007, the genre wasn’t as popular. 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. 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. 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. 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. How does an idea for an essay or a book come for you? 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. So, the struggle shifted from being a sign that I should stop to just being a part of the process. As for taking a nontraditional path, it depends what your goals are. Mentors have shaped my life, definitely. Smith. Smith: That would be funny, if someone became a writer to be rich. 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. Do you like playing that mentoring role? 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. Smith by Emily J. The biggest thing I’ve learned from teaching is that no essays are “worth” more than others. 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. Smith   is a writer and the founder of   Chorus, a matchmaking app where friends swipe for friends. 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. Do you journal or have a daily writing practice or any rules like that? 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. Is your impression that things are harder or easier for new writers, now? 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. It could take three more years, and that thought is daunting. With books, I have no idea. Emily has published in the The Rumpus, Catapult, Salon, Slate, Hobart, among others, and frequently writes for Medium. 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. What does that even mean to you? 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! Do you like writing longer-form books? With essays, when they become boring to work on, I know it will be over soon. When I have an idea or am excited or passionate about a project, though, I’m a motivated and fast writer. 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. Emily has published in the The Rumpus, Catapult, Salon, Slate, Hobart, among others, and frequently writes for   Medium. Smith and Chloe Caldwell

By Emily J. Smith
July 20th, 2020

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. 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. ***
Photograph of Chloe Caldwell by JD Urban. And, if I don’t write for a few months, I turn into a crabby bitch. Caldwell: In the sense that I’ve been able to write and publish my books in the way I wanted to—yes. Do you have any preference between working on that kind of project and working on essays? Smith: Do you consider yourself a successful writer?