How’s the Writing Going, Deesha Philyaw?

“For me, getting better as a writer is learning how to get to the essence of things and boil down all of that exposition and backstory.”

This is a column called How’s the Writing Going? It’s the question no writer wants to be asked—but which every writer wants to ask others. We want to know that other people are struggling the same way we are or to learn other writers’ hacks and antidotes for blocks and other challenges.

Here I chat with Deesha Philyaw about interrogating writer’s block, working on multiple projects at the same time, and how character can drive plot.

Deesha Philyaw’s debut short story collection, The Secret Lives of Church Ladies, won the 2021 PEN/Faulkner Award for Fiction, the 2020/2021 Story Prize, the 2020 LA Times Book Prize, and the Art Seidenbaum Award for First Fiction. The collection was also a finalist for the 2020 National Book Award for Fiction. The Secret Lives of Church Ladies focuses on Black women, sex, and the Black church and is being adapted for television by HBO Max with Tessa Thompson executive producing. Deesha is a Kimbilio Fiction Fellow and will be the 2022–2023 John and Renée Grisham Writer in Residence at the University of Mississippi.

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Sari Botton: So tell me what’s going on with you and your work.

Deesha Philyaw: I’m packing to move, going on vacation, and writing. And I’m also teaching.

SB: Where are you moving from and to?

DP: I have lived in Pittsburgh since 1997. So for twenty-five years, which is half my life. And I have always been planning to leave. My youngest daughter graduated from high school this year. I didn’t know where I was going to go, but I knew it was away from here. Then the pandemic hit as I was sort of planning. And then, after my book came out, the University of Mississippi offered me the John and Renée Grisham Writer in Residence opportunity. So I will be there for the 2022–2023 academic year. I have a light teaching load at the university because the purpose is for me to write my next book, and the best part is I get to live in John Grisham’s old house on seventy-seven acres.

SB: So you’re writing a new book. That’s exciting. How’s the writing going? And has it been maybe a little easier now than it might have been in the depths of, say, pre-vaccination Covid-19 times?

DP: I’ve been writing a lot since 2020, prior to my book coming out that September. When the pandemic hit, one of the things we could keep doing safely was reading and writing. And so I’ve written a lot of short stories. I’ve been working on a novel. I also started working on a YA novel, and The Secret Lives of Church Ladies story collection is being adapted for television, and I’m writing that as well. So I’m just bouncing around between projects. But in the back of my mind, I think, I really should be working on the outline for my novel because my agent is waiting on that. It’s like whack-a-mole. Whack-a-mole is how it’s going.

SB: You’ve also got a new podcast, Ursa Story, with author Dawnie Walton and Longreads founder Mark Armstrong, focused on short fiction and amplifying underrepresented writers. You are doing a lot! Is this new for you, this whack-a-mole approach, or is it part of how you’ve always worked?

DP: I’ve always worked on more than one thing at a time and sometimes in more than one genre at a time. I’ve also been writing some essays during the pandemic as well.

SB: I sort of work that way too. I call it “cheating.” I often need to toggle between at least two projects. When I’m stuck on my primary project, I need to be able to cheat on it with another one. And then when I get too stuck on the other one, I need to cheat on it with the primary project.

DP: I like that. When I have a deadline looming, I kind of zero in, like I’ve got to bang this out. But up until that time, I’ll waffle back and forth between different things. In February I got to spend a month alone in Miami just to write. I thought, I’m gonna spend a week finishing up the short story that I’ve been working on. And then I’ll spend three weeks working on the novel. It ended up being the opposite; I spent three weeks working on this story and then had a week just to work on the novel. It was fine. I thought, Excuse me, the story took as much time as it needed to take.

SB: Are you struggling with the novel?

DP: Well, I had stopped working on my novel a long time ago. Because I was stalled on the novel, my agent suggested I work on the short story collection, because I had some stories. So it was her idea to write Church Ladies. After I turned in the manuscript for Church Ladies in 2019, I thought, I understand now why I got stuck on the novel. Now I’m gonna pour myself into the novel. And then I didn’t. Then Church Ladies came out and I started working on more short stories and essays. I started writing personal essays about divorce and also dating again and then trying to date in the pandemic. Those were things that I kept thinking, I’m not gonna write about this, but then I couldn’t stop writing about them. I was taking writing workshops and teaching a writing workshop at the same time. I was really stimulated, and I think that’s why I was so productive during that time.

SB: Sometimes I think you have to be open to what wants to be written when. If you don’t surrender to that, you can really get your mind jammed up. Did you figure out what was jamming you up about the novel, or was it just not the time for it? Did the other things need to be written first?

DP: It was the fact that I had no interest in my character at all anymore, and there was no story there. I had more of a situation, an idea, but there was no story. There was very little at stake. The main character was way too much like me. She was only doing things that I would do. And she saw the world the way I saw it. She didn’t take any chances. I didn’t let really bad things happen to her. I made her so nice. So there was nothing there. I was bored. But I kept trying to write her. Well, I shouldn’t say I kept trying to write her. I kept thinking to myself, I should be writing my book right now, but I realized it wasn’t that I couldn’t figure out how to write the story. I just lost interest. And I think acknowledging that for myself, that I was no longer interested in this character, was important.

My agent was really helpful in this process. She said, “What part or parts do you like about the novel?” She asked, “Are there characters you like, or scenes? What parts are you excited about?” And it was the main character’s best friend. The scenes with the two of them, when they were girls, I still laugh at. That character’s backstory, I think, is incredibly funny and interesting. I didn’t think about stakes until later. Part of the plot was my character risks losing everything, but she also didn’t really like her life. My agent was like, “So what if she loses everything, if she’s losing something she really doesn’t want anyway?” It’s like having a character lose a job they hate. Of course they’ve got to figure out how to pay the bills, but that can’t be the story. If a character loses a job that they love, you have more of a story. If they lose it and it’s totally unfair and no fault of their own, and they’re being railroaded and they’re a whistleblower, that’s a story. What I had to learn how to do is basic novel writing, just basic storytelling—raising the stakes. I taught a workshop this summer, and there was a woman who also had a story about a woman who was unhappily married. I was teaching a craft lesson on raising the stakes. I asked, “What does your character want? What is the value of that thing? It has to have some value. And how can you make it complicated for them to get it? Or what is at risk? What might make them lose it?” She said exactly what I had been saying for years: “It’s not that she wants something, it’s that she got what she wanted and she’s not happy with it.” I said, “Well, then the story’s over. Now what does she want? She has to want something, and you have to make it really hard for her to get it. Then you have a story and then there are some stakes.” And that’s what I had to do for myself too.

SB: So you’re now working on this novel again?

DP: I’m working on the outline of it. I’ve written a couple of chapters, and now I’m doing this process called the snowflake method where you basically outline the characters and what they want and who they are. And that becomes the outline for the novel itself.

What I had to learn how to do is basic novel writing, just basic storytelling—raising the stakes.

SB: So “character is plot,” as one of the Greeks said, I think.

DP: Yeah, exactly. I don’t outline my short stories, but for this novel I’ve kind of mapped things out.

SB: Are there ways in which you get in your own way as you’re writing? I know that often I have to trick myself into getting started, especially when I have multiple deadlines. I have to promise myself a cookie if I work for an hour. Or I have to Pomodoro my way through it: Let’s just set the timer for twenty-five minutes. Do you ever get so stuck that you have to, like, make bargains with yourself about how to get going?

DP: I think I—what did you call it? Cheating. I cheat when I get stuck. So I’m rarely just stuck across the board. When I’m stuck on my girlfriend story, I know that it’s time for me to go home to my husband story. And then when I get stuck again, I go back to my girlfriend. Other times, if someone asks me, “What are you working on?” and I have to be succinct—I can be very long-winded—in just describing what I’m working on to another person, I can have a little breakthrough. Like, oh, that’s what this is.

SB: Yeah. I think talking is really good, especially with other writers.

DP: Sometimes it’s just time away from the writing—leave it, come back. I’ll see things that I didn’t before.

SB: That is such an important thing for me also; I need to put writing away for a bit, especially if it’s giving me a hard time or even if I think it’s amazing, I need to put it away and come back to it a week, two weeks later. The mind just does its own thing. Too often I think writers get caught up in “I’m not writing enough. I’m not producing enough words. I’m not sitting long enough for long-enough periods.” I feel like the breaks are almost as important as the periods when you’re throwing yourself in there and writing.

DP: I think it’s also knowing yourself and the difference between this is the kind of break that leads to a breakthrough and this is just me avoiding and playing on Twitter. Although, sometimes playing on Twitter can lead to the breakthrough, you know? But we know ourselves. It’s good to know when we need to rein ourselves in and when it’s like, no, this is good. This break is writing, this time away is writing. This is part of the larger process of writing.

SB: There’s some anonymous Twitter account where it’s just all the non-writing things that qualify as writing. Like walking your dog is writing, cooking dinner is writing. It’s kind of true. Sometimes you need to do the Zen thing of another activity. You’re always writing, even when you’re not sitting at your computer or at your desk writing longhand, however you write.

DP: We hopefully know the difference between that and, say, avoiding it, because of what people typically call writer’s block or imposter syndrome. I am not a licensed therapist, but I really think that it’s something else. We’re worried about what somebody’s going to say, or there’s too much pressure to perform. Or we don’t think we have a right to write the thing we’re writing about. Or we’re already worried about marketing. Rather than face those things, sometimes we go, “Oh, it’s imposter syndrome. Oh, I have a writer’s block.” Because if we interrogate what’s really going on, we’ve got to do something about it.

SB: Pressure is a huge obstacle. I’m always trying to find ways to lower the stakes for myself. Shitty first draft. Pomodoro for twenty-five minutes. Kill the perfectionist.

DP: Yeah, silence that voice. What does Anne Lamott call it? KFKD, the radio station that’s playing in your head. “You can’t do this,” or “How dare you,” or whatever unhelpful thing is being broadcast about you and your work.

SB: Earlier you referred to yourself as long-winded, but I think of you as such an economical writer. You achieve so much in such a spare way.

DP: That’s come with time, because when I first started writing twenty years ago, I was explaining everything. Exposition was everything. And really, unless you’re Toni Morrison, you really can’t get away with that. That’s not to say all she writes is exposition—it’s just that she writes it so well. At the outset, my exposition was a couple of things happening. One, it was me telling myself the story, which is how a lot of us write drafts. Over time I’ve gotten more economical about that. For me, getting better as a writer is learning how to get to the essence of things and boil down all of that exposition and backstory.

The second reason is that I was in a place where I felt like I had to explain myself all the time. I didn’t trust myself as a writer. I didn’t trust the reader to get it. And that had everything to do with feeling misunderstood and unheard in my personal life. The first time I tried to write about my father it was like twenty pages. Like a deposition, an indictment, everything he had ever done wrong. And it just poured out. I had two writing mentors at the time, and I asked them, “So tell me, where should I submit this?” And they both said, “Nowhere. This is a journal entry.”

SB: Wow. You wrote about him so beautifully for Pipe Wrench magazine.

DP: Thank you. One of my mentors said, “All emotional expression is not artistic expression,” which is a nicer way of saying, “Keep that in your journal.” Over the years, I’ve learned how things move from your journal to a literary journal. The next time I wrote about my dad was like fifteen years later. I think the essay is under five hundred words. That’s all I felt like I needed to say because I was in a different place by then. I didn’t have that same little-girl need. I could approach it as someone who had started to heal from some of those things. After I wrote that essay, I was like, That’s it, I’m not writing about him again. And then Pipe Wrench magazine, here they come. The way Pipe Wrench works is like a literary dinner party. They give you an essay that several writers are all responding to, and you can write whatever you want. The main piece for that issue was an essay about generations of black men in Los Angeles who tend to pigeons and train them to compete in flying competitions. I immediately started thinking about my father, not because he’d ever done that, but I immediately thought, Well, if my dad had done something like this, maybe he would’ve been a better person. And then I went, Oh, I can’t write that. And then, I guess I’m gonna write that.

SB: Okay, one last question. I know that for me, the judicial coup the right-wing majority of the Supreme Court is in the midst of—including the overturning of Roe v. Wade, which forecasts the destruction of more basic rights and bodily autonomy—has greatly affected my brain. It has ratcheted up my own sense of terror, and burying myself in work until I can’t think straight seems to be the only antidote. Well, that and donating to abortion funds, et cetera. Is it having a similar effect on you? Does it infringe on your ability to get work done?

DP: As a Black woman and mother in this country, I’ve had to learn to focus and write in the midst of endless terror. For centuries, we’ve had a scream and a song coexisting in our throats. Our stories are our balm and testimony.