My toddler is home sick from preschool, and I’m recovering from a hacking cough that I’ve had for several weeks now. Plus, my cat has decided that the moment I hop on Zoom with Cheryl Strayed is also the moment he’ll wake up from his 22-hours-a-day nap to jump on my desk and walk in front of the computer’s camera. So when Strayed, best-selling author, subject of a hit movie adaptation, and advice columnist behind Dear Sugar, admits that she herself is also “both falling apart and holding it together simultaneously,” I feel a real sense of relief.
“Even though you and I know this—you know my life is fucked up, and I know your life is fucked up and also not fucked up—we all project onto others,” she tells me. “We think, Well, they have it all together, and they have this ease and this sense of self-assurance or whatever. That’s a story we tell ourselves.”
That willingness to share her own imperfections and vulnerabilities has been at the epicenter of Strayed’s writing from the very beginning. Her 2006 novel, Torch, loosely based on her own life, follows a family in crisis after the death of the mother, while her 2012 memoir, Wild, chronicled her own journey hiking the Pacific Crest Trail. Later in 2012, she wrote Tiny Beautiful Things, a collection of essays from her Dear Sugar column, in which she shares her own life experiences while answering readers’ often heartbreaking questions.
Tiny Beautiful Things has now been adapted into a limited series starring Kathryn Hahn, which will begin airing on Hulu on April 7. Hahn stars as Clare, a writer whose personal and professional lives are in shambles when she’s asked to take over a popular advice column. Much of the inspiration for Clare, though not all of it, comes from Strayed’s own life. It’s the second adaptation of her life for the screen, following Wild, the 2014 film starring Reese Witherspoon as Strayed. Both Wild and Tiny Beautiful Things, at their cores, grapple with a woman struggling with the loss of her mother to cancer.
I point out to Strayed that I can’t think of another living writer who has had so much of their own personal life adapted for both the big and small screens. “Nobody is as surprised as me,” says Strayed. “I do believe that no matter what happens in my life, I am really always going to be that girl who grew up literally without indoor plumbing in rural northern Minnesota, who just dreamed of being a writer but didn’t dream any of this. I mean, I couldn’t even imagine it.”
Frankie (Merritt Wever) and Clare (Kathryn Hahn)By Jessica Brooks/Hulu.
When Strayed was first in talks with Witherspoon about adapting Wild, she asked herself a few questions: “Do I trust this person? Do I think that this person understands what my intentions were as a writer? And do I think that they will honorably bring their vision to the world that isn’t counter to the book?”
For her, the answers were yes, and Wild was the beginning of a long-lasting working relationship and friendship between Strayed, Witherspoon, and Laura Dern, who also starred in the film. Even back in 2014, they talked about the idea of adapting Tiny Beautiful Things into a TV series. But things really began moving when Witherspoon introduced Strayed to showrunner Liz Tigelaar, whom she was working with on Little Fires Everywhere. “We met and immediately hit it off,” she says. “I sensed that she had a really articulate, sensitive, generous, compassionate view of the world and of this book.”
Strayed was comfortable with the movie version of Wild being based completely on her life, but told Tigelaar that she wasn’t as open to doing the same with this show because parts of it center on her life today. They agreed that the character’s past would be the same as Strayed’s—her mother died young of cancer; she grew up poor in a rural environment; she is estranged from her father who was abusive; she got married young and got divorced young. But the present is largely fiction. “Liz Tigelaar always says it’s like Cheryl, except she didn’t hike the Pacific Crest Trail, and she didn’t write her first book or her second book or her third book,” she says. “It’s Cheryl without the writer and the wilderness journey.”
The show follows Clare, a writer whose marriage is falling apart because she lent a large sum of money to her brother without telling her husband. A friend recruits her to anonymously write the Dear Sugar advice column, an unpaid gig that Clare does not feel qualified for. But, as she starts to dole out advice, she begins to unpack her baggage from her past, including her grief from the death of her mother.
