How Ada Calhoun Became a Bestselling Author

In late 2017, Ada Calhoun, BA ’00, felt busted and blue. The UT alumna from New York City had been a freelance writer for two decades. Her work had appeared in Time, O magazine, National Geographic Traveler, The New York Times, and on the New Yorker’s website. She was also an A-list ghostwriter. Yet the books she’d penned under her own byline, her 2015 history book St. Marks Is Dead and 2017 memoir Wedding Toasts I’ll Never Give, sold slowly despite dazzling reviews in The Atlantic, The Washington Post, and The New York Times Book Review

Wondering when it would ever feel like she had truly made it, she slipped into despair. “I thought my career was over,” Calhoun says. “There I was in my early 40s feeling unsuccessful, unsexy, and unsure if I could bring home the bacon the way Enjoli perfume commercials from my childhood promised.” She didn’t know if she’d ever publish another book.

Then Calhoun, 44, got frank. She unburdened her soul in a cathartic 6,000-word essay titled “The New Midlife Crisis.” The article explained why so many Generation X women, born between 1965 and 1980, were feeling exhausted, underemployed, cash strapped, and shortchanged.
“Is it any wonder that women our age possess a bone-deep, almost hallucinatory panic about money?” she asks in the essay. “We’re some of the best-educated women in history, and yet we’re downwardly mobile; about two-thirds of us have less wealth than our parents did at the same age.” The essay exploded like internet dynamite. Women—and editors—devoured the story and wanted to know more. Soon Calhoun had a book deal that changed her life. 

Why We Can’t Sleep hit shelves in January 2020 and quickly made the New York Times bestseller list. The Alcalde asked Calhoun about her latest book and her career path.

Find Inspiration

Calhoun took a gap year after high school and traveled to India, where she met Mother Theresa, read the Upanishads, and relished old languages, like Sanskrit, Bengali, Kannada, and Tamil. After studying Sanskrit for two years at McGill University in Montreal, she enrolled as a junior in UT’s Sanskrit program to learn from renowned Indologist Patrick Olivelle. “When I got to UT, we were proofreading Olivelle’s definitive translation of the Upanishads. It was like magic,” Calhoun says. “Our homework was to read proofs for his books and find typos.”

Take Initiative

Calhoun began her writing career while she was still an undergrad at UT, authoring freelance book and theater reviews, feature stories, and profiles for the Austin Chronicle. That’s also how she met her husband, Neal Medlyn, who was a performance artist doing shows at Wooldridge Square Park in October 2000. “I was sent to profile him for the Chronicle, and my editor said, ‘Don’t be alone with him. He seems crazy,’” she says. Calhoun and her roommate were the only two people who attended Medlyn’s show that night. “We fell in love, and we’ve been together for 20 years.”

Be Versatile

Growing up, Calhoun knew she loved languages, reading, and writing, but she didn’t know what to do with her interests. “I wound up studying this obscure thing at UT, but it gave me all these skills,” she says. Today she attributes her ghostwriting success as much to her Sanskrit training as she does to her journalism experience. “I can listen to a celebrity telling a story, and I know how to translate it into a book in the way I would read something in Devanagari and know how to translate it into English verse.” By pursuing her passions in all directions, Calhoun devised a journalism and a ghostwriting career. She also teaches nonfiction, memoir, and proposal writing at conferences and book fairs nationwide. “You just never know,” she says.

Develop Thick Skin

Working on the crime desk at the New York Post in 2010, Calhoun often had to interview victims of violent felonies and the perpetrators who committed them. “People would hang up the phone on me,” she remembers. “They didn’t want to talk to me during a terrible moment in their lives.” Calhoun had to learn not to take it personally. This lesson would steel her against future criticism and teach her how to extract sensitive information from subjects.

Be Honest with Yourself

“A huge part of freelancing is rejection,” Calhoun says. “I’ve been through times when I was hardly making any money and big projects have fallen through.” Books don’t always hit either. When St. Marks Is Dead came out, it exceeded sales expectations, so Calhoun received a bigger advance for her next book. When it sold about the same as St. Marks, she worried she had disappointed her publisher and editor. “In the publishing world, it’s true sometimes that a sales tract affects whether you get another shot.” She wrote honestly about her struggles, which led to her big break. Why We Can’t Sleep made the New York Times bestseller list in January. The book also relieved her financial strife, fostered camaraderie with women in America, and solidified her purpose as a writer.

Filter Criticism

Calhoun prefers to focus on what she can control and the positive ways people respond to her work. “One thing that’s helped me to accept criticism is realizing that nothing will ever be everything to everybody,” she says, noting that it’s rare for a book to yield amazing sales, reviews, and prizes, change people’s lives, and please the writer. Why We Can’t Sleep earned some negative reviews—The Wall Street Journal said it was whiny. “I thought, ‘You know, I could dwell on that and be upset it didn’t get five out of five stars in every newspaper, or I could think, I’m receiving all these messages from women who said it made their lives better, and was profound for them,’” she says. “It’s OK if a critic doesn’t think it’s the greatest book.”

Find Your Own Salve

Calhoun hears from Why We Can’t Sleep readers regularly. Here is some of the wisdom they have shared: Reevaluate the expectations you had for yourself growing up and see if maybe you were sold a bill of goods; assemble an Ocean’s 11-esque team of trusted helpers—a pet sitter, mechanic, therapist, plumber, and an accountant who understands your financial situation; join a club; find a good gynecologist; and, above all, realize this period of time doesn’t last forever.

Give Back

Calhoun gives feedback to young writers and co-founded the Sob Sisters, a monthly career-development night for journalists held at local bars in New York City. She has won numerous awards for her national news reporting and will serve as the first nonfiction mentor for the Miami Book Fair’s new Emerging Writer Fellowship program. When she’s not overworking, Calhoun enjoys hiking in the Catskills with her husband, son, and stepson. Her upcoming memoir about her father, his favorite poet Frank O’Hara, and life in lockdown during coronavirus is expected next year.

Images courtesy Ada Calhoun


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