Tough love

The inside flaps of just-released book, Tiny Beautiful Things: Advice on Love and Life from Dear Sugar, are covered with nuggets of wisdom: “Forgiveness doesn’t just sit there like a pretty boy in a bar.” “Every last one of us can do better than give up.” “Walk without a stick into the darkest woods.”

That last bit is especially poignant because, on Valentine’s Day of this year, The Rumpus.net’s advice columnist Dear Sugar (anonymous since late ’08) revealed herself to be author Cheryl Strayed. A month later, Strayed’s memoir, Wild: From Lost to Found on the Pacific Crest Trail, was published — a best-seller, optioned for a film by Reese Witherspoon, and made an Oprah’s Book Club pick by Winfrey herself, who relaunched said book club — a 2.0 version, no less — just so she could tout Strayed’s work. In it, Strayed goes very literally into the darkest wood without a stick.

She does have an absurdly large backpack.

And a pink ski pole, rescued from a free box.

And her insights, gleaned from the loss of her mother and an untethered upbringing that led to a series of unfortunate decisions. To counteract those (an unplanned pregnancy, divorce and drug use), Strayed embarked — in her mid 20s, with no real hiking experience — on an 1,100-mile trek of the PCT.

All of which is to say, Strayed’s advice as Dear Sugar comes from a place of having lived what she preaches. Tiny Beautiful Things is culled from Strayed’s column and includes never-before-published questions to and answers from Sugar.

So, yes, two books in a mere six-months: Practically unheard of in the publishing world, but what both Wild and Tiny share are Strayed’s very personal revelations. “I went through that panic where I thought, ‘Oh my God, why did I make it a memoir?’” Strayed says of Wild. But she also says that, from the beginning, “I knew this wasn’t going to be fictionalized.”

Strayed’s debut, Torch, was fiction, though (like her Dear Sugar column) it borrows heavily from real life. “People read it like a biography, but it’s really not,” she says. In that book, the main character’s mother dies suddenly and her siblings scatter when their stepfather quickly remarries. These are prominent themes in Wild, too, though while recounting the details (both her successes and dismal failures on the PCT) Strayed is unflinching. She talks about her extramarital affairs, about the hot date-worthy underwear she sends to herself in a drop box (hikers pick these up at scheduled stops to replenish their supplies) and about the way her mother’s death haunts her.

“You have to so inhabit any given experience to really write about it vividly,” Strayed says. The hardest memory to revisit in Wild was “the scene in which my brother and I have to kill our mother’s horse. It was more brutal to write than it is to read, and I know a lot of people say they couldn’t bear to read it,” she says.

Strayed is equally fearless when it comes to letters her Dear Sugar readers send: “When I was six and a half months pregnant, I miscarried. Since then, I’ve struggled to get out of bed,” writes one. “I take a month’s supply of some very strong pain meds in about seven to 10 days, then I crash and have to beg or borrow from others to make it to the next appointment,” writes another.

In her answers, Strayed (who took care of her dying mother, kicked heroin and doggedly pursued her dream of becoming a writer) is both direct (“Do you own a pair of steel-toed boots? I do. And I’m happy to loan them to you so that you can properly kick the ass of that fool,” she says of a deadbeat dad situation) and tender, calling those to whom she doles out advise “sweet pea” and “darling.” She also talks a lot about personal experience: “I got married when I was in college. I got divorced during the years that I was lying about having an English degree,” she writes. And, more bluntly, “My father’s father made me jack him off when I was 3 and 4 and 5.”

It’s probably this everything-on-the-table approach that’s won fans for Strayed for decades, from the group of fellow hikers in Wild who named her “Queen of the Pacific Crest Trail” because people were always helping her out, to Oprah, who “just called me up on my cell phone, out of the blue.” Strayed says, “I almost didn’t take that call, because I didn’t recognize the number.”

— Alli Marshall can be reached at amarshall@mountainx.com.