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Cheryl Strayed Has Inspired Millions to Travel. Now She’s Prepping for Her Next Journey

‘Wild’ Author Cheryl Strayed on life, travel, and her new Hulu show, ‘Tiny Beautiful Things.'

Chances are you’ve heard of Cheryl Strayed.

She is the author of Wild: From Lost to Found on the Pacific Crest Trail, a New York Times best-seller and international phenomenon that has sold over 4 million copies worldwide and been translated into 40 languages. In 2014, Wild was adapted into a major motion picture starring actresses Reese Witherspoon and Laura Dern, who both earned nominations at the 87th Annual Academy Awards.

Wild tells the story of Strayed’s life-transforming hike along the Pacific Crest Trail (PCT)—the second longest trail in the United States, stretching from Mexico to Canada through California, Oregon, and Washington. During her 1,000-plus-mile hike, Strayed grappled with the sudden death of her mother and her ensuing grief, turning towards the wilderness as she literally and metaphorically searched for a way out of the woods. Her journey has inspired countless others and legions of soul-searching hikers, creating what has since been dubbed the “Wild Effect.”

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“I love that so many people have explored the Pacific Crest Trail because they read Wild,” Strayed tells me one afternoon via Zoom. “It feels like a wonderful legacy, and I’m so grateful for it. And it’s not just people hiking the PCT; it’s people hiking other trails throughout the world or simply daring to walk alone.”

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Strayed is every bit the warm, kind, and lovely woman that she appears to be on paper. Her light blonde hair cascades over her shoulders, contrasting with her dark-framed glasses. She listens to my questions intently and responds earnestly, engaging as one would a friend over a coffee rather than a journalist via Zoom. Despite becoming a public figure and best-selling author, Strayed remains remarkably grounded—she is a writer and artist humbled by how people have internalized her words.

“One of the most common questions I get is, ‘How have you changed?’ I swear to God, the only way I have changed is that I can pay my bills on time and can maybe buy nicer boots than I used to,” she laughs. “That’s the way I’ve changed. I’m not a different friend. I’m not a different mother. I’m not a different wife. I’m not a different writer. I’m not a different person. I don’t have a different opinion of myself.”

Wild has become a permanent fixture on my bookshelf since its publication in 2012. I first read it when I was in my mid-twenties and running away from my impending wedding, finding solace in Strayed’s words as the lost woman on the page mirrored my own uncertainty. I held Wild close to my heart like a salve when I traveled alone for the first time on a trip to Argentina, sleeping with the book pressed against my chest like a talisman against the anxiety and loneliness tailgating my travels. Rereading Wild in my thirties bolstered my resolve to pen my own travel memoir, remembering the power of Strayed’s words and drawing inspiration from her pages. In reading how Strayed’s hike changed her on an almost molecular level, I found similarities in how traveling has inspired endless waves of transformation in my own life.

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“I’ve come to think of Wild as the kind of trip that is like a rite of passage, which is a very ancient medicine,” muses Strayed. “In ancient times, many cultures would give young people rites of passage so they could clearly see where they’ve been, where they might go, who they are, and come to grips with some of the harms they’d endured or some of the ways they’d harmed others. These trips are like accelerators; it’s how we grow. Would I have realized all the things I realized about my grief and my mother had I not hiked the Pacific Crest Trail? I think I would have eventually, but my trip was a deepener and an accelerator. We really need that sometimes. I needed to change my life, and hiking on the Pacific Crest Trail allowed me to do that.”

Looking back on Strayed’s hike, it is almost funny how woefully unprepared she was. From her too-small boots to her too-large backpack (lovingly nicknamed “Monster”), she’s been criticized by outdoor experts for her lack of preparation. But, to read Wild is to know that Cheryl didn’t choose the PCT so much as it chose her. Standing in line at a store, waiting to purchase a foldable shovel, her eyes landed on a guidebook called The Pacific Crest Trail, Volume 1: California. She considered the book and its images of blue skies, crystalline lakes, and craggy mountains and then placed it back on the shelf and left the store, only to return for the book later.

“The Pacific Crest Trail wasn’t a world to me then,” writes Strayed in Wild. “It was an idea, vague and outlandish, full of promise and mystery. Something bloomed inside me as I traced its jagged line with my finger on a map.”

When asked how her relationship to travel has evolved in the years since she hiked the PCT, Strayed explains how it’s within the unexpected moments of a trip that she finds clarity.

“When we imagine a trip, we imagine the idealized version of it; that it is just going to be easy and fun and glorious, and we’re going to be in paradise,” she tells me. “Then things happen. Hard things, unexpected things, unwelcome things—they become the meaning of the trip. They become the things you remember and the stories you tell. I think that life is like travel in that way.”

Courtesy of Hulu

‘Tiny Beautiful Things’ Comes to Hulu on April 7th

Sitting on my bookshelf alongside Wild, equally dog-eared and marked up, is my copy of Tiny Beautiful ThingsOriginally published in 2012, Tiny Beautiful Things is a collection of essays inspired by Strayed’s “Dear Sugar” columns.

For those unfamiliar with “Dear Sugar,” Sugar was the pseudonym used by Strayed in an advice column for The Rumpus, an online literary and culture magazine. Written anonymously, Strayed (a.k.a. Sugar) would respond to heartfelt questions about loss, heartbreak, love, identity, addiction, marriage, and life. Although the original column has since ended, Strayed continues offering thoughtful advice via her “Dear Sugar” newsletter.

To read Tiny Beautiful Things is to immerse yourself in the beauty, complexity, ugly, and endearing aspects of the human experience. The unbridled honesty of the questions is in itself disarming, but it is Strayed’s thoughtful answers that shine light into the darkest depths of the reader’s emotional fortress.

“I’m not talking to people from the elevated position of ‘I’m the one who knows, and you’re the one who asked the question, so sit back and listen.’ Instead, I give a kind of horizontal advice,” explains Strayed. “I’m gonna get right down there in the mud with you and grapple with this question you asked and tell you what I’ve learned. That’s the way I give advice.”

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On April 7th, Tiny Beautiful Things will be adapted into a Hulu series starring actress Kathryn Hahn, who plays Clare, a struggling writer turned beloved advice columnist doling out help amidst her own life struggles. Based loosely on Strayed, Clare differs in the details, except for her past, which pulls inspiration from Strayed’s childhood and core memories.

“I am an executive producer [alongside Reese Witherspoon and Laura Dern] on the project and was also one of the writers on the show,” Strayed tells me over Zoom. “Liz Tigelaar, the show creator and showrunner, is this amazing human I just learned so much from about television writing. The show tells the story of this 40-something woman (Clare) who is figuring out what it means to help other people through their struggles as she herself struggles. It’s dramatic, funny, and sexy. I hope everyone loves it.”

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After my interview with Strayed, I walk over to my bookshelf and pick up the copy of Wild that I’ve now carried for 10 years. A passage at the very end of the book sticks with me in which 26-year-old Cheryl Strayed has just finished hiking the Pacific Crest Trail, walking a thousand miles from the Mojave Desert to Oregon’s Bridge of the Gods. Wild toggles between present and past tense until this last passage, in which Strayed jumps ahead to reveal a glimpse of her future. Time collapses and suddenly, we’re left with the powerful image of a twenty-something Strayed seeing herself years from now on this very same bridge, slurping ice cream cones with her future children and husband.  

In 1995, Strayed might have never imagined all that life would have in store for her. From an international bestselling book to film and television adaptations of her work to a loyal fanbase who hold her words like mantras, it seems her real journey began just as her hike ended. Today, Strayed is once again on the precipice of something transformative.

“One of the things I love most about being 54 is I have learned that in difficult times, something powerful and beautiful almost always emerges. This helps me get through the hard times, knowing that I’ll look back on this experience and see it as a gift in some way,” says Strayed. “Now here I am in middle age, wondering what’s next? What’s this next era about? I can feel it in my bones that a journey is coming. My kids leave the nest in a couple of years, and I’m longing for a journey to help me see the road ahead clearly.”

Cheryl Strayed_credit Holly Andres
Penguin Random House;
Penguin Random House;
Holly Andres

A Rapid-Fire Travel Round With Cheryl Strayed

Would you prefer a getaway to the beach or the mountains?

Do you choose a window or aisle seat?

Describe your travel style in a few words?
“Foot speed,” because even when I’m not hiking, my favorite thing to do is just wander around.

What is your best small piece of travel advice?
Always bring a hoodie on your flight.

How about your best big piece of travel advice?
I think of travel as what I call “retrospective fun.” You almost always look back and say, “wow, that was so much fun.” Even though it was miserable, or you were lost, or you lost your keys to the room, or you couldn’t find the place you were supposed to go, it’s almost always fun in retrospect. Remember that about travel and life.