Into the Wild with Dear Sugar, aka Cheryl Strayed

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Into the <i>Wild</i> with Dear Sugar, aka Cheryl Strayed

In 1995, Cheryl Strayed was 26, freshly divorced and turned-on to heroin, a few months past an abortion, and for all intents and purposes an orphan on her own in the world. With no place to be and no one to be any place with, she found a book in a store, traced her finger across a line on a map, and decided to follow that jagged line across the mountains of the Pacific Crest Trail.

Wild is the true story of how walking that line took Strayed from where she started to the person she is today—a successful, critically acclaimed writer and also the voice behind the beloved advice column Dear Sugar. In the column, she doles out advice anonymously (Spoiler Alert: The author revealed her identity this Valentine’s Day, reasoning people would read this new book and figure it out for themselves anyway) with just the right combination of toughness and warmth, a balance she also walks in this book like a tightrope.

That sure balance also makes Strayed a powerful advocate for VIDA, the organization she helped found in support of women’s writing. Both Strayed and her alter-ego Sugar are feminist, but their feminism is not just hard the way some people mistake all feminism to be. It is soft and warm too.

Full disclosure: In 2002, at the age of 21, depressed and set on dropping out of college, I put my finger on a line on a map in a book and decided to walk that line until whatever had shut off inside me turned back on again. (I’m pretty sure this is a Sugarism, and if not, it is definitely inspired by recently re-reading all of Strayed’s writing to prepare for this review.)

The line my finger traced was the Appalachian Trail. I have struggled since with how to write about that specific experience. Though, like Strayed, I emerged at the other end of that wilderness tunnel in better physical and mental shape than I went in, it’s been particularly difficult terrain to retrace with a pen. Reasons?

1. A huge part of the whole point of long trail hiking involves monotony, repetition and Zen. You do it because you want to replace the ups and downs of daily life with the ups and downs of your feet. You do it because you want to be able to see your future literally stretching out before you on the horizon. Peaceful, difficult repetition with a view during day after day of hiking clears out your brain and gives you massive, muscled legs … but not much in terms of plot development.

2. Everyone moves at his or her own pace. (The cliché is true.) So, the people you meet on a long hike appear for brief interludes and then disappear. This poses a real problem in creating lasting, memorable characters.

3. What do people who have not spent months living in the woods and pooping in holes every day find most interesting about hiking a long trail? The idea of being surrounded by the serene beauty of nature for a long time. The catch is that the longer the serene beauty of nature surrounds you, the more you crave comforts. The journal from your long hike should fill with descriptions of plants and beautiful vistas, but you arrive home to find fantasies of warm baths, glamorous outfits, hot food and lipstick.

4. Hiking a long trail, you endure bad things. You run out of water and have to walk a long distance and drink from a muddy pond. You fall down with all your possessions strapped to your back and you get up bleeding and keep walking. You find yourself in a situation with a strange man—exactly the kind of strange man you have always been warned to stay away from. You eat terrible instant food that leads to nearly erotic dreams about the mediocre food that regular people eat all the time. Why? You have deliberately inflicted all of these obstacles and sufferings on yourself to prove how tough you are. But the main thing you end up proving is how stubborn you are—that you can put one foot in front of the other for a longer time than most other people.

In writing about this crazy suffering you brought upon yourself, it is difficult not to sound a bit spoiled and whiney. True even if—like Strayed—you spent literally every penny you saved waitressing to fund your hike or, like me, you telemarketed for six months. You imagine the reader thinking, “If she is so miserable, why doesn’t she just get off the trail and stop whining?”

In Wild, Strayed faces these writing obstacles with the same bravery and insight she used to face obstacles that confronted her on the trail. I kept thinking of her first book, Torch, where she described how a character’s advanced cancer felt prior to diagnosis: “As if her spine were a zipper and someone had come up behind her and unzipped it and pushed his hands into her organs and squeezed, as if they were butter or dough, or grapes to be smashed for wine.”

In Wild, the Pacific Crest Trail is the spine of the book. It’s too straight to sustain a narrative by itself, so Strayed has unzipped it and forced emotionally packed scenes from her life between sections on backpacking.

Fans of Torch and/or Dear Sugar will recognize life events Strayed mined first for her novel and then her advice column. These include: an absentee father who abused her mother until she left him; a poor rural upbringing; a loving but struggling mother largely responsible for transforming her children’s poverty into a kind of pioneer utopia; that same mother diagnosed with late-stage cancer before her 50th birthday; Strayed’s infidelity and promiscuity in the wake of her mother’s death; divorce from a man she still loved but felt compelled to leave; waitressing; heroin; unwanted pregnancy; eventual success as a writer; and the formation of her own happy family.

Strayed says different kinds of truths emerged when she wrote her experiences in different ways. One kind of truth appeared first in her fiction. A second supports the advice she gives as Sugar. A third level of truth surfaces in the memoir form of Wild.

“On my hike, as I moved forward physically, I also moved back into my life,” she explains. “I spent whole days thinking about one thing, one person, one mistake, one era of my childhood. It was like I was working my way through it, completely out of chronology, while I was putting one step in front of another. My mom died when she was 45, and it ripped my life apart. Everything I write is informed by that experience, and different truths arise from it in my writing depending on the form.

Wild is all about the messy business of what happened. The voice is more intimate, more raw, perhaps. There are a few very, very hard emotional scenes in Torch, but a few of the scenes in Wild almost killed me to write. I had to go all the way there, down deep, not into what I could imagine, but into the things I’d rather forget and can’t because I’m terrible at forgetting.”

Wild shares with Dear Sugar and Torch the idea that sometimes you have to mess up and have negative experiences to become extraordinary. Early in Wild, Strayed writes:

“I would walk that line, I decided – or at least as much of it as I could in about a hundred days. I was living alone in a studio apartment in Minneapolis, separated from my husband, and working as a waitress, as low and mixed up as I’d ever been in my life. Each day I felt as if I were looking up from the bottom of a deep well. But from that well, I set about becoming a solo wilderness trekker. And why not? I’d been so many things already. A loving wife and an adulteress. A beloved daughter who now spent holidays alone. An ambitious overachiever and aspiring writer who hopped from one meaningless job to the next while dabbling dangerously with drugs and sleeping with too many men.”

Later, after hiking more than a thousand miles, she continues:

“What if I forgave myself? I thought. What if I forgave myself even though I’d done something that I shouldn’t have? What if I was a liar and a cheat and there was no excuse for what I’d done other than because it was what I wanted and needed to do? What if I was sorry, but if I could go back in time I wouldn’t do anything differently than I had done? What if I’d actually wanted to fuck every one of those men? What if heroin taught me something? What if yes was the right answer instead of no?”

This type of thinking makes Strayed, aka Sugar, such a fitting advice columnist for our modern age. Time and time again, whether in Torch, Wild, or Dear Sugar (the column is the most popular regular feature in the Rumpus, a web magazine that gets 500,000 page views a month), Strayed tells her readers it doesn’t matter what has come before. They can … and they deserve to … pick up the pieces, move forward, become whole.

The light Strayed shines on her hiking experience isn’t only internal. Through our wilderness guide we witness azaleas in “a dozen shades of pink and pale orange.” We see black bears that are not black but cinnamon brown and blonde, bleached like surfers by the California sun. We walk among blackberries, chaparral, cottonwoods. She offers coyotes, granite cliffs, Joshua trees, manzanitas, monkey flowers, mountain lions and wind-twisted foxtail pines as a kind of factual, natural nutrition to sustain us through trials on the trail.

Strayed also provides a comprehensive ethnography of the people who hike long trails or live near them. We meet miners, motel owners and homeless people not entirely mistaken in thinking Strayed is one of them. An interviewer for The Hobo Times gives her a “hobo survival kit.” Trail angels perform random acts of kindness, offering free burgers, beer, and foot massages. We learn about gear, food and Spartan quarters.

As in Lidia Yuknavitch’s (Yuknavitch is in Strayed’s writing group) critically acclaimed memoir The Chronology of Water, Strayed’s memoir includes details of adventurous risks she took in her youth and a description of the family she formed later. She speaks of this family often in Dear Sugar, lending advice on what it means to be a wild woman who ends her unconventional journey as part of a somewhat-conventional family.

“One thing that Lidia and I have often discussed,” Strayed says, “is how women like us have been interpreted and essentially colonized on the page. And by women like us I mean women who were and are bold or rule-breaking when it comes to things like sex or drugs or desire or even how we make our art.

“Our culture still hasn’t evolved terribly far beyond the good girl/bad girl dichotomy. It’s more comfortable for many to think we are one or the other. But Lidia and I are both, just like most humans are. We’re all both good and bad, fucked up and totally sound, full of remorse and entirely unapologetic. One thing I think Lidia and I are doing when we show you how our lives are now, how it is that we’ve built these whole, happy, even traditional-seeming families, is that we’re saying we’re not sullied by what came before.

“In fact, we are made by it. And our lives are not something that’s behind us, but something that’s a part of us. We are healed now, but we are still the complicated and hungry girls we were before.”

Sara Faye Lieber’s essays have been published in Guernica, Gigantic, Narrative, Pank, and other places. She is currently working on a book about animals that live indoors.

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