Tiny Beautiful Things is a forthcoming Hulu series adapted from a book that was culled from an anonymous online advice column. All of which might sound like a strange route to television, but Cheryl Strayed has never walked a straight path. She started writing a column under the pseudonym “Dear Sugar” more than a decade ago when she was a struggling writer trying to cobble together a living. Strayed didn’t really have the time to write for free or the authority to dispense wisdom, but she did it anyway, knitting her own gutting life experiences into empathetic and essayistic replies that quickly made her an internet cult figure. 

That status was further boosted by Wild, Strayed’s memoir about her life unraveling after the death of her mother when she was 22 and her decision to hike the Pacific Crest Trail alone. While making Wild, Strayed talked about adapting Tiny Beautiful Things for the screen with Wild stars Reese Witherspoon and Laura Dern, who are both executive producers on the Hulu series. “There was so much life and story in each of these little letters that were written to me,” Strayed tells Vanity Fair. “And the letters I wrote back to people were just full of all the things I love to see when I watch television or movies—the real stuff of life.” Strayed took a swing at writing scripts over the years, and eventually Witherspoon introduced her to Liz Tigelaar, a veteran showrunner who’d worked with Witherspoon on Little Fires Everywhere. “I felt like she understood the soul of the book, and that we were going to be in good hands.” 

Strayed points out that the middle-aged Clare is not her alter ego: “She is somebody who I have a lot of things in common with, but her present day life is not my life. The things that are happening in her marriage are not the things that are happening in my marriage, her child is not mine.” This fictional character does, however, share many fragments from the author’s past. “She had to be somebody who struggled for money all of her life like I did,” Strayed says. “She had to be somebody who lost her mother as she herself was becoming a woman, and she had to get married scandalously, ridiculously young, as I did. She had to have feelings inside of her that hurt…because those are the things that formed my psyche.”

Casting Hahn was a crucial step, because they knew they’d found an actor who could radiate humor and compassion while also convincingly sabotaging herself at every turn. “Kathryn feels like she could be everybody’s best friend,” Tigelaar says. “There’s something about her that is so magnetic, her essence kind of draws you in…. She lets herself be real, messy, flawed.” Hahn could pull off the juggling act of “complete fucked up–ness and lovely togetherness,” Strayed says. “She’s also a woman who’s held down a job and gotten health insurance, raised her kid, and stayed married to this guy.” In the writers’ room, Strayed would sometimes describe her past self as “a little bit heroin-y”—having used heroin in the ’90s without becoming a junkie—and that was also incorporated into the series. 

Strayed is joyful about putting such a complicated figure on the screen, knowing that fictional female characters are still sometimes skewered for it. She says that when the movie version of Wild came out, she was stunned by the discussions about Reese Witherspoon’s character—that is, Cheryl Strayed—as an unlikable woman. “I was like, What? Likeability has never been my problem,” she says and then chuckles. “But that was shorthand for complexity—somebody who does some things that you’re not supposed to or that maybe are contradictory.”

Hahn’s character in Tiny Beautiful Things can’t stop doing things she’s not supposed to. She has passed the age that her mother was when she died, and yet Clare has not become the writer—or the person—her mother believed she could be. “It’s a really unique way to tell the story of a life, a nonlinear memoir,” Tigelaar continues. “Like we’re comprised of all these little dots of the stories that make us, and we’re pulling out dots in no particular order, weaving them together into this tapestry to say: [These are the things] that created you, and this is what you have to draw from now.”

Those stories often resonate painfully for Clare, who remembers with horror how unappreciatively she received her mother’s last present. “It’s a very particular thing to lose a parent when you’re a teenager or in your young twenties,” Strayed says. “That group of people has a tremendous amount of regret and guilt, because they were regular teenagers. And in the last years of their mothers’ lives, they treated their mother like shit, you know? I had to grapple with that, too—going back in time and being like, I should have been more grateful for that coat she bought me in the last Christmas of her life.” She shakes her head. “But you have to live with it, you have to forgive yourself, you have to do all the things you have to do. And I love that we got to tell that story in this show.”

Tigelaar recalls that cast and crewmembers whose lives had been touched by loss often swarmed Strayed when she came on set, recognizing themselves in her evocation of grief as a long and steady hum, rather than something you get over and stay over. In fact, Strayed once wrote in a Dear Sugar column that her own writing comes from “the divine place within me that is my mother. Sugar is the temple I built in my obliterated place.” Strayed wanted to make sure that came through in the series, too. “At a lot of points in this season, everything’s all messed up,” she says thoughtfully. “The thing I find so moving about this character is that she leans in the direction of empathy and kindness and telling people that they can—that they can find love, that they can believe in themselves, that they can go on for another day—in the form of this advice column. She’s the conduit for not only the best parts of herself, even when everything’s gone to hell, but the best parts of us.” Editing from Phyllis Housen, ACE and Costume Design by Alana Morshead.