Cheryl Strayed Will Always Be Here for You

On the edge of Wallace Park in Portland, Ore., there is an unremarkable house with a camellia shrub out front. The house is painted a bluish gray now, but it might have been another color before. Cheryl Strayed is standing on the sidewalk in the rain with a smile on her face, conjuring a memory. This is where she took part in a yard sale in 1995, immediately after she—now quite famously—completed a 1,100-mile solo hike on the Pacific Crest Trail. At the time, she was a 27-year-old aspiring writer with 20¢ to her name. She sold whatever she could, including a pencil sharpener to a man who rode in on a bicycle. The man invited her to dinner with some friends, and later that night, Strayed met the person she would marry.

Strayed sees them everywhere: little signs, small reminders. It’s one of the things that define her writing, that ability to draw connections—whether between a yard sale and the life she’s built with her husband, or between a cry for help from a reader and a lesson she’s learned from her own past.

Strayed, 54, has built a career on her dual abilities to tell the whole, ugly truth about herself and to empathize with others, creating a space for self-acceptance. Wild, the 2012 memoir of her Pacific Crest Trail journey, told the story of the sudden loss of her mother to lung cancer when Strayed was 22; her subsequent struggles, including a heroin habit and a divorce; and the hike that brought her back to herself. That book, which was adapted into a 2014 film starring Reese Witherspoon, has sold more than 4 million copies worldwide. It also launched Strayed’s “accidental” career as a public speaker, for which she has traveled the world teaching writing and speaking to people about the great dreams and traumas of their lives, offering whatever wisdom and encouragement she can.

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It was a fitting shift. Before Wild made her a household name, Strayed was going by another one: Sugar. In 2010, two years before Wild shot her to literary stardom, Strayed took over the advice column “Dear Sugar” for the online literary magazine the Rumpus. It was a no-pay job answering reader letters in the voice of a woman with a checkered history first dreamed up by the writer Steve Almond, and he was ready to pass the mantle. For two years, as Sugar, Strayed anonymously responded to letters seeking advice on everything from whether to have children to how to overcome jealousy. Instead of offering the practical guidance given by most advice columnists, Strayed treated each missive like an essay, sharing bits of her personal story to make broader points about the beauty and agony of being human.

A collection of the columns, Tiny Beautiful Things, was published just a few months after Wild. Strayed and Almond launched a podcast, Dear Sugars, in 2014. Nia Vardalos adapted Tiny Beautiful Things into a play in 2016. And now, on April 7, Hulu will premiere a television series of the same name. Strayed executive-produced and helped write the series, with Little Fires Everywhere alum Liz Tigelaar serving as showrunner. With their team, they created the story of Clare (played by Kathryn Hahn and, in scenes from the past, Sarah Pidgeon), a mother whose life is crumbling when she’s asked to take over as the columnist Sugar.

Sugar is, well, sticky. Her story keeps getting remade, and Strayed couldn’t shake her if she tried. She and Almond stopped making their podcast in 2018; the Rumpus column was already long done. But strangers never stopped writing to her. They found her personal email or wrote to the old “Dear Sugar” address, seeking a piece of her wisdom. So she started a monthly newsletter. Giving advice is part of her now. The writer and the persona are inextricably linked. And it’s precisely because they—both Sugar and Strayed—have lived through dark times, erred, and never claim to have all the answers that the advice is so potent. “I’m not some wise guru who’s like, here’s how to live,” Strayed says, ambling along on our rainy walk. “I’m right down there in the muck with you.”

Tigelaar likes to say that adult Clare in the emotional Tiny Beautiful Things is an alternate-reality version of Strayed, one who never hiked the Pacific Crest Trail and never wrote Wild; now 49 and devastated that she hasn’t fulfilled her promise as a writer, she drinks too much, she creates chaos, and her marriage, her work, and her relationship with her kid are all suffering. But, divergent as their present-day realities may be, the Clare character and Strayed share the same history: both married the wrong person too young, both lost their mothers to cancer during their senior year of college, and both fell into self-destruction.

There is a scene in Tiny Beautiful Things when Frankie (the mother of young Clare, played by Merritt Wever) calls Clare home from college. She resists—she’s busy, she has work and class and a life on campus—but Frankie insists. We see Clare enter the house where she grew up with her mom and her brother Lucas, the table set for an unusually formal dinner. Her mother is wearing lipstick and a nice dress. She made spinach lasagna and bought ice cream for dessert. Clare fumes. “I can’t just come home just because you miss me,” she says. This is when Frankie tells her children: she’s going to die.

“I get chills even saying this to you,” Strayed says. “That was straight from my life.” She had the surreal experience of sharing the story of how she learned of her mother’s illness in the writers’ room for the series, then watching the actors play out the scene. The same thing happened with Wild. “Who does this?” she says. “It’s like, OK, people, now you’re going to re-enact Cheryl’s 10 most painful moments, and Cheryl’s going to sit there and watch, sometimes over and over.”

Strayed being Strayed, she found something heartening in the scene. Watching young Clare storm into the house with her selfish, early-20s attitude, Strayed recognized that any young woman trying to establish her independence might behave the same way. She couldn’t have known what her mother was about to reveal. Observing Pidgeon step into the character, Strayed says, “I feel such a sense of gentleness for the younger version of myself … It’s the most specific and bizarre form of therapy.”

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This is the story that she has carried with her for more than 30 years. It was the subject of her first book, the 2005 novel Torch, of Wild, of so many important moments in the “Dear Sugar” column and Tiny Beautiful Things in all its forms. With the show, Strayed emphasizes that she wanted to tell a “true story” about grief. Clare’s problem is not that she hasn’t moved on from her mother’s death, she explains. A primal loss like hers is a trauma that re-emerges again and again. When Strayed had her first child, she had to reckon again with her grief, and when she turned 45 and outlived her mother, she did again.

She likens grief to a box you’ll hold forever—what it means to you is determined by how bravely you look into it. “Anyone who reads my work or sees the show knows how very much I have turned my deepest sorrow into beauty,” she says. “That’s what grief is. If we work really, really hard, we can get to that place.”

The rain is coming down harder, so I set our course toward a coffee shop I know nearby. With the glowing storefront in sight, Strayed suddenly stops, looking downward. I follow her gaze. I see a penny in the middle of the sidewalk, wet and a little grimy. She sees another sign from the universe: there are good things here. “I’ve had all the luck,” she says, urging me to take it. Instead, I suggest we leave it for the next person to find, so she bends down to touch a finger to the surface, transferring some of her good fortune.

Shaking off the wet as we enter the café, I realize the mistake I’ve made. There it was: my chance to claim a little piece of Strayed’s magic for myself. That’s what we congregants of Sugar do. We take her words of encouragement and sympathy, her tough love and her powerful example, her belief in humanity, and we tuck them in our pockets and hold onto them.

Inside, we sit down and continue the conversation. Strayed tells me she’s working on another memoir, a project she’s been wrestling with for a while. She tells me more about her family, about awkward times when she’s been recognized in public, about her writing process. Then, on the walk back to where we started, she brings me right to the spot where we left the penny. It’s still there, shinier than before. “It’s destiny,” she says.