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At 28, Cheryl Strayed Had An Epiphany That Paved The Way For Wild

The writer finished her legendary Pacific Crest Trail hike just before her 27th birthday. Here’s what happened next.

Cheryl Strayed, Wild and Tiny Beautiful Things author, reflects on life in her late 20s.
Jon Kopaloff/Stringer/Getty Images; Courtesy of Cheryl Strayed
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Cheryl Strayed became a literary sensation in her 40s with the blockbuster memoir Wild, in which she tells the story of how, in her 20s, still reeling from her mother’s death four years earlier, she clawed her way up from rock bottom by hiking 1,100 miles on the Pacific Crest Trail. With each solitary step from California’s Mojave Desert to Oregon’s Bridge of the Gods, she shed sweat, toenails, and shame over her years of grief-driven self-destruction.

Strayed revisits these themes — brokenness, the struggle for redemption — in much of her writing, and they’re front and center in Hulu’s Tiny Beautiful Things, an eight-episode adaptation of the author’s 2012 book, which anthologizes her advice column, Dear Sugar.

“You can’t let the worst things that happen to you stop you from getting what you want, and if you do, that’s nobody’s fault but your own,” actor Merritt Wever says in one scene, in a sentiment that’s a guiding principle for Strayed. (On screen a version of the author is played by Kathryn Hahn; Wever plays a woman modeled after her mother.)

Strayed’s early circumstances would top most people’s list of “worst things”: She survived abuse at the hands of her father and grandfather, and also poverty that left her home without electricity or indoor plumbing. But it was the devastating loss of her mother, Bobbi, that would become the propulsive force of her life and work.

“Those years when I was 27, 28, 29, and 30, I was rebuilding my life in a way that made room for the fact that I would carry with me the great sorrow of my loss.”

Bobbi, who fled a violent marriage to raise three kids in a house she built by hand in the Minnesota woods, died at 45 of lung cancer, seven weeks after her initial diagnosis. In the aftermath, Strayed came undone. There was reckless promiscuity, divorce from her first love, and a dalliance with heroin. She has often explained how her implosion was a sort of misguided tribute to her mom: “To prove her life mattered, I became determined to blow up the life I’d begun to build,” Hahn says in a voiceover on Tiny Beautiful Things. “The life my mother had wanted for me.”

That was the life she resuscitated on the PCT. “When I went off on my hike, I was in a bottom point of my life,” the author, now 54, tells Bustle. “I wasn’t saying, ‘I need to go on this hike because I need to become a different person.’ It was, ‘I need to be returned to myself.’”

Strayed stepped off the PCT two days before her 27th birthday. Nine days later, while crashing on a futon in a friend’s spare room, she sold most of her belongings in a very fortuitous yard sale. She sold an airplane-shaped pencil sharpener to a guy who’d introduce her to her husband, and a pair of overalls to a woman who tipped her off to a job at a fancy French bar, where she waited tables until she could afford to move into a Portland loft (“I painted the walls black,” she says, “totally badass”). The next year, she took a job as an advocate for at-risk middle school girls.

“Those years when I was 27, 28, 29, and 30, I was rebuilding my life in a way that made room for the fact that I would carry with me the great sorrow of my loss,” she says. “[I learned] that from my suffering, if I kept moving in the direction of my deepest intentions — to become a writer, to become a thriving, happy person — that that sorrow over losing my mom would become the source of many good things in my life. And I wasn’t wrong about that.”

Below, the author and ongoing advice columnist talks about rescuing yourself, responding to infidelity, and the advice she needed at 28.

Courtesy of Cheryl Strayed

I’ve just spent a week reading your work and crying a lot.

Aw. Thank you. I love to make people cry.

When you stepped off the PCT, about to turn 27, what did it take to rebuild your life?

Those late-20s years were my real and final entry into adulthood. I was humble enough to realize, I’m always growing, always learning, always making mistakes. And mature enough to realize that if I was going to do all this stuff I said I was going to do, I was going to have to be the person to do it. As I wrote in “Write Like a Motherfucker,” there was this weird feeling, all through my 20s, that some great bird would swoop down and be like, “Congratulations! Your novel has been written!” And around 28, 29, I was like, “Oh, geez. My novel hasn’t been written. And I really need to figure out how to do it.”

As I approached my 30th birthday, I decided to apply to graduate school. I got married in August 1999, and our honeymoon was driving a U-Haul truck with two cats from Portland to Syracuse. My MFA program was basically my paid gig so I could write my first book. Within a couple weeks of finishing it, it had sold to Houghton Mifflin.

In “How You Get Unstuck” you describe working as a youth advocate for “barely teenage girls” who were living through horrific situations. Your advice to them was “to run as far as you can in the direction of your best and happiest dreams, across the bridge that was built by your own desire to heal” and “to swim like f*ck away from every bad thing.” Your message was that no one is coming to your rescue, that you have to rescue yourself. Had you reached that realization by 28?

Absolutely. One of the things I learned on my PCT hike, which ends up being a core piece of advice I give over and over as Sugar, is the power of acceptance. That radical, simple, incredibly difficult act of accepting that what’s true is true, and then moving from there. So much of what happens to us when we’re struggling is about resistance. I don’t want my mom to be dead. I don’t want… fill-in-the-blank. But once you can say, “This burden I’ve been saying I can’t carry? I’ve actually been carrying it all along. So how about I learn to carry it with grace, courage, or strength?”

That’s what I was trying to tell those girls. It’s not fair that they had the lives they had, and yet they only had two options: Do you let that thing be the thing that kills you, or do you decide, I will try to make something beautiful of this?

I loved those girls. It was the job that changed my heart, mind, and life in so many ways. And even then, in this incredibly rewarding job, I had this terrible sinking feeling in my gut. A voice within me was saying, “This job is not what you’re here to do. You are a writer, and you have to answer that call or you’ll always have this feeling in your gut.” That was the job I quit when I went to graduate school.

We tend to fear being perceived as “trauma dumping” or “oversharing” when we’re open about our pasts. But doesn’t everybody have trauma? Do you wish people would talk more openly about it?

I absolutely think most of us have some kind of trauma, but it’s hard to compare traumas on a scale. Rather it’s, “Did something happen to you that made you feel like you couldn’t go on?” For one person, it might be an argument [with] a friend, and for another it might be that your mother was murdered in front of your eyes. [We think] there’s this scale, that one is clearly worse than the other. But we all live our own lives. The worst thing that happened to you is the worst thing that happened to you. It’s hard, and it hurts, and it’s scary, and you have to find a way to survive it.

In my work as Sugar, where people are opening their hearts up to me, and when I teach writing workshops, there’s always pain in the room, but there’s always triumphant beauty, too. There’s always healing, recovery, and forgiveness. When we’re vulnerable and tell the truth about who we are, we recognize each other. That’s what vulnerability does. It creates a forum where we can speak honestly.

If you could have written to Dear Sugar at 28, what would you have asked?

I think I would’ve asked a question I’m still asking, about how it is that we, women and girls and female-identified people, feel OK in our bodies in a culture that absolutely hates women, and hates women’s bodies, and subjects us to such impossible, narrow, and rigorous standards of beauty and attractiveness. [How do you] learn to actually love yourself and honor your body and inhabit it with a sense of ease, joy, and confidence?

It’s something that, sadly, has been a lifelong journey — not just for me, but for a lot of people. And I would’ve asked Sugar to help me through that.

What advice do you have for not letting the past resurface and drown you?

Again, I’m a big believer in acceptance. The past isn’t something we leave behind; it’s something we carry with us. That doesn’t mean we’re constantly dragged back, haunted, or burdened by an old story of ourselves. But you say, “OK, I’m going to take that past experience, revise it, and write it into the story of me.”

There’s a column in Tiny Beautiful Things called “A Bit of Sully in Your Sweet,” where I write about learning that my husband cheated on me before we were married. At the time, I was like, “I want to leave that in the past.” And yet, the work we did by saying, “OK, wait a minute. This isn’t going to be like, ‘You’re bad, you need to make amends, and onward we go.’ But rather, ‘Why don’t we use this as an opportunity to open up a conversation about monogamy, honesty, sexuality, desire? What if we let that be a part of our story that makes us stronger?’”

Moving on is about taking command of the stories that have been handed to you, and revising them so that they tell a deeper truth about who you are and who you intend to become.

This interview has been edited and condensed for clarity.