Woman of Letters

When Cheryl Strayed was 25, she wrote a fan letter to Alice Munro. Strayed had just received two copies of her first published story–“One for you, and one for your mum,” the publisher told her–but her mother was dead, and “Alice Munro was my god,” she says. So she sent the second copy off to Canada with a note. She didn’t expect a response, but the doyenne of short fiction wrote her back. “You must continue writing but you do have lots of time,” Munro said. “I wasn’t writing nearly so well at your age.”

Munro’s letter, a page of looping script, hangs framed in Strayed’s bedroom, where–on her laptop, in a blue armchair–she answers letters from people seeking advice. They sign their letters with names like “Crushed,” “Suffocated” and “Stuck.” Strayed signs hers “Yours, Sugar.” Now 43, she is the author of a collection of Dear Sugar columns called Tiny Beautiful Things, to be published in July. Her memoir Wild, which was published in March, tells the story of her solo trek along the Pacific Crest Trail when she was 26, a journey she undertook to help her recover from two overwhelming griefs: the loss of her mother four years earlier to cancer and the breakup of her marriage. It was well received when it came out and will be widely read this summer thanks to Oprah Winfrey, who made it the first pick of her newly relaunched book club.

Many of the pieces in Tiny Beautiful Things, which first appeared in the online literary magazine the Rumpus, have had robust first lives, circulated on the Internet by fans. In book form, the letters and Strayed’s responses take on greater meaning as an extended epistolary essay on the human condition–with its antsy spouses, frustrated parents and desperately indebted students–and also as a companion autobiography to Wild. Sugar’s technique is to share the thorniest, most indelible experiences from her life to help each letter writer work through his or her own, which makes Tiny Beautiful Things an odd, contradictory and moving invention: an anecdotal memoir–that most narcissistic of genres–whose every chapter is written lovingly and generously to someone else.

When strayed began writing as sugar in March 2010, taking over for her friend the writer Steve Almond, she had never read a self-help book, aside from a pregnancy manual. “I didn’t read advice columns in any intentional way,” she says. But she had stories. She had cared for her dying mother, then missed her deathbed by an hour; gotten married and divorced and married again; shot heroin into her ankle; worked as a waitress and a youth advocate; published a novel; had an abortion and given birth to two children; moved abroad; broken her heart; and lost six toenails to the trauma of hiking in ill-fitting boots.

And she had her own pantheon of advisers–not Miss Manners or Ann Landers but Munro, Mary Gaitskill, Edna O’Brien, William Maxwell. “Flannery O’Connor was my self-help,” Strayed says. “Stories, poems–they have been my guiding lights. I thought, Why not give others what I’ve received from other literary forms?” Instead of offering plain old prescriptive advice, in other words, she could offer her experience. Sugar was a fictional character, “a woman with a troubled past and a slightly reckless tongue,” as Almond writes in the introduction to Tiny Beautiful Things; he’d invented her with Stephen Elliott, the founder and editor of the Rumpus. Strayed had just sent off the first draft of Wild to her editor. She felt up to the challenge of making Sugar’s voice her own.

She knew she risked becoming that friend who hijacks your plea for help, drowning out your problems with hers. But she noticed pretty quickly that readers of Dear Sugar, without even knowing who Sugar was, wanted to hear her stories. The one about how her mother alleviated the pain of her father’s abandonment (addressed to “Oh Mama,” a woman whose baby’s father won’t make good on his promise to be involved in the child’s life), the one about her friend who committed suicide after suffering burns over his entire body (addressed to “Beast with a Limp,” a man who wonders if his physical deformities mean he should close himself off from romantic love), the one about learning to live with the death of her mother (addressed to “Living Dead Dad,” a man paralyzed by grief at the loss of his 22-year-old son, who was killed by a drunk driver)–those are the columns people loved.

“She has a tremendous empathy, which is the hallmark of a literary writer–the ability to put yourself in someone else’s shoes,” Elliott says.

“Therapy in the town square” is what Strayed calls it, except nobody’s really the therapist. “I’m actually trying to work against the tradition of know-it-all advice,” she says. “I say to people, I know that you’re all f—– up, because I am too, or I have been too.”

Sugar is sharp-witted, but she doesn’t do funny. She doesn’t do snarky. (This distinguishes her from, to state it conservatively, most of the Internet.) And Sugar doesn’t coddle. She especially doesn’t coddle writers. Breakfast at Strayed’s house in Portland on a sunny May morning features her husband Brian Lindstrom, a documentary filmmaker, 8-year-old son Carver (named for Raymond), 6-year-old daughter Bobbi (named for Strayed’s mother), fruit, bagels, veggie sausage and coffee in a mug that says WRITE LIKE A MOTHER——, which is available for sale on the Rumpus site. It’s the last line of Sugar’s response to a woman who wants to be a writer but is crippled by her conviction that she’ll never be as good as David Foster Wallace.

Because of the literary nature of the Rumpus and her openness about her own publishing career, Strayed hears from aspiring writers more than your average advice columnist does. On her mind is that letter from Alice Munro and both the heady nature of praise and the slippage between praise and success. She thought twice about taking the Sugar job for financial reasons: the work is unpaid, and she’s still paying off her college loans. One of the harshest columns in Tiny Beautiful Things is her response to a young writer prone to bitter envy over friends’ book deals. “The thing is, because it’s close to my heart, because I’m a writer too, I want her to succeed,” Strayed says of that piece. “And the only way she can do that is to get the f— over this.” Another thing Sugar doesn’t do is watch her language.

She has that in common with Strayed. They’re not quite the same person, but they sound a lot alike. Which means that when you talk to Strayed, on the futon in her book-filled home office, you find yourself asking questions only to jointly pick them apart. “I do tend to be somebody who, if you came to me with a problem, I would help you dismantle it so we could see it more clearly,” she says. Often in Sugar’s most exhaustive dismantlings, no answer materializes. “You have the feeling as she starts to write that she doesn’t know what the answer is going to be. It becomes like a detective story,” Elliott says. “And then she honors the contract. The contract is, if you follow her on her exploration, she will show you what she finds, no matter how uncomfortable that is for her.”

The explorations can get very uncomfortable, but that’s what keeps them from being too blithely be-your-best-self-and-shine. The first Dear Sugar column Strayed wrote that really exploded was in response to an offhand rant in which the writer asks “WTF?” three times over. After describing in detail episodes of sexual abuse at the hands of her grandfather, Sugar tells the writer, “Ask better questions, sweet pea. The f— is your life. Answer it.”

Strayed finished her college work by correspondence in 1997, six years after she was meant to graduate. She’d grown up in the country north of Minneapolis and went to the University of Minnesota determined to emerge a writer, a sophisticate, someone of consequence. But her mother was diagnosed with cancer and died during the spring of her senior year, and there was one last English paper Strayed couldn’t finish. She later arranged with the college to complete the requirement with Latin 101 from Portland, Ore., where she moved 17 years ago. “I did it the old-fashioned way,” she says. “In the mail.”

That was two summers after her hike on the Pacific Crest Trail, for which she prepped boxes of supplies to be mailed to post offices along the way, with a few small bills in each–all the money she had. One is struck, reading Wild, by how different it was to be adventurous in 1995, how much more quiet and solitary it was to be alone. Weighted down by her overstuffed backpack, no room for a Walkman, Strayed crafts a mixtape in her head (Lucinda Williams, Michelle Shocked); the books she reads each night, she burns as she goes. There are no cell-phone warnings of ice and snow in the Sierras, just a young woman on her own with an ice ax, who tells herself she is not afraid in order to not be afraid.

That stillness pervades Strayed’s Dear Sugar columns, which profit from all the advantages of the Internet–its anonymous e-mail forms, endless terrain and capacity for comments and community building–but provide refuge from its white noise. It’s partly because of the emotional content of each letter and response but also due to the inherent intimacy of the form. Direct address is as old as lyric poetry: it’s just I and you, and the rest of the world gets to listen in. Most listen kindly. “You’d think that I’d be deluged with mean e-mails,” Strayed says, but on the whole, in Sugar’s corner of the online world, niceness prevails.

Strayed officially revealed herself as the “I” behind Sugar in February. She plans to write the column less frequently now, in part because she doesn’t want to repeat herself–“How many stories does one woman have?” she asks, only half rhetorically–but also because she’s writing other things. She’s working on a long essay called “Places We’ve Never Been,” about the first trip she took by herself, in her pickup truck in the American Southwest. She’s researching a novel in which one of the main characters is an astrologer. She wants to try her hand at creating a fictional TV series based on her column. Reese Witherspoon has optioned Wild for film development, with herself to star and Lisa Cholodenko, who made The Kids Are All Right, in talks to write and direct; their hope is to start shooting next summer.

And Strayed is fielding questions–as Sugar and as Cheryl. At readings, people ask her, Are your feet O.K. now? (Yes, she says, though “it took a few years for my toenails to be normal again.”) Should we hike the Pacific Crest Trail this summer? (“Go!” she says. “Do it!”) At the breakfast table, knowing I have come to talk to his mother about her writing, her son asks, Are we characters in this story? She dismantles the problem into the distinction between characters and people, which gets to the heart of her ambition. “The thing that I always wanted most to do is write stories that seemed like real life,” she says of her work. To write characters so real that they move people–characters like Sugar.

FOR MORE ANSWERS FROM CHERYL STRAYED, GO TO time.com/strayed