Deesha Philyaw did not teach me how to write, but she did teach me how to turn writing into a career. I have spent many hours on the phone with her asking what I should charge for a certain piece of content, or where to submit my work. She is a kind human being who has always cheered on her friends and contemporaries, so seeing her win—and win big—over the past three years has been a thrill.
If anyone knows how to make entrepreneurship and writing look easy, it’s Philyaw. The Secret Lives of Church Ladies author signed a seven-figure book deal with Mariner Books in September for her debut novel, The True Confessions of First Lady Freeman, and another short story collection called Girl, Look.
A seven-figure book deal is very impressive. But anyone who knows Philyaw knows that she has the hustle it takes to make writing a business. In 2011, when I was a baby content writer looking to make a decent side hustle out of the only thing that I’ve ever been really good at, Philyaw taught me lots of tips and tricks—and always told me to never accept less than I’m worth.
To be a writer you need to be entrepreneurial
The business side of writing can be tough. Writers need to be business savvy and understand the ins and outs of how to sell as a writer. There are also very important nuances that first authors need to understand when they go out to query an agent.
“[It’s] not just writing an agent and sending them your work and telling them how great it is,” Philyaw says. “There’s actually a format for how you query an agent and what you send and what you don’t send and when you send it.”
Like many career writers, Philyaw started out as a freelancer. She also knew that she wanted writing to be her career.
“It’s been entrepreneurial from the beginning,” she says. “Once I knew that, I wanted to try and make a living at writing and not just write as a hobby or for my personal benefit. And that was when I was getting divorced. I was like, ‘I’m gonna have child support and alimony for a while, but eventually I got to try and make this work.’”
“I was gunning for publication,” Philyaw continues. “The problem in the beginning was that I was writing novels, and it takes a long time to write novels. And so that’s not a thing that’s gonna get you paid right away on a regular basis to pay your bills.”
Philyaw submitted her work wherever she could, though she admits the way she went about it didn’t quite make sense. “I was not writing things that were a good fit for these prestigious publications. But I wanted the prestige because I wanted to build my byline and I also wanted to get paid more,” she says.
How Deesha Philyaw got her first break
This was before the economic collapse of 2008, when media outlets and magazines paid freelancers quite well. Surprisingly, it was an unpaid writing job that started to bring Philyaw real work.
“I saw a call for a columnist for a site called Literary Mama. I pitched a column called ‘The Girl’s Mine’ about being an adoptive parent, and they liked it,” Philyaw says. “And so that was not a paying gig, but I did it for four years for free. It was one of the ones where exposure really did pay off because that’s what got me on the radar of national print publications, newspapers and magazines. And editors started reaching out to me about publishing things with them.”
“One of the editors reached out and invited me to pitch him and I was like, ‘Thank you so much. How do you pitch?’” she recalls. “I had no idea how. And now you know, in retrospect, I probably should have asked someone else or just googled… But he was so kind and he taught me how to pitch him. Then I pitched him, and then I ended up writing several pieces for his magazine and that was great until, again, the economy collapsed.”
When the magazine Philyaw had been writing for ultimately went under, she had to diversify her workflow. She began writing parenting articles and writing for businesses wanting to outsource work. Since she was writing parenting content and had a healthy co-parenting relationship with her ex-husband, Philyaw and her ex co-authored a book called Co-parenting 101: Helping Your Kids Thrive in Two Households After Divorce.
“The co-parenting book came out in 2013,” she says. “And that’s how I got an agent. And that agent knew I was working on a novel, and she was encouraging me to finish it so she could take it out on submission.”
Philyaw’s big hit: The Secret Lives of Church Ladies
Eventually Philyaw’s agent noticed a theme across the short stories Philyaw was still writing.
“She said, ‘You know, I really liked these church lady stories,’” Philyaw recalls. “She called them that—I didn’t really notice the through line between them.”
These church ladies ended up receiving a tremendous reception. Philyaw’s short story collection, The Secret Lives of Church Ladies, was a finalist for the National Book Award (sometimes described as “The Academy Awards of Literature”) and won multiple awards, including The Story Prize, The Los Angeles Times Book Prize and the PEN/Faulkner Award. It is also being adapted into a drama series for HBO Max with both Philyaw and playwright Tori Sampson writing the script.
It is rare for a short story collection to be so successful, but Church Ladies struck readers and critics alike.
“People in publishing will tell you short story collections don’t sell; they’ll always want you to try and sell a novel first,” Philyaw says. “And they’ll also tell you you can’t sell things on a partial manuscript, but my agent believed otherwise.”
In spite of her tremendous success, Philyaw still takes the time to mentor other writers, teaching them how to think strategically and making helpful industry connections.
“The success of Church Ladies gave me a degree of power that I did not have before,” Philyaw adds. “I can use that to empower writers who are coming after me.”
Photo by Vanessa German.