For Cheryl Strayed, 2012 was one hell of a year. Wild, the Portland-based writer’s memoir about hiking the Pacific Crest Trail (PCT), alone, at age 26, while bearing the unbearable in every way ​— ​including doing it in a too-small pair of hiking boots ​— ​debuted at number seven on the New York Times best-seller list in March. Even before its release, Reese Witherspoon optioned it for a film, and, soon after Wild achieved best-seller status on its own, Oprah resurrected her book club to name it her first pick.

The year also saw Strayed outing herself as Sugar, beloved advice columnist on the website The Rumpus, known for sharing deeply personal stories in her responses. Tiny Beautiful Things, a compilation of Dear Sugar columns, published in July.

Cheryl Strayed

In both Wild and Tiny Beautiful Things, Strayed stands out for her disinterest in taking cover: She deals in naked honesty. Her grief over her mother’s death (which she writes about in Wild and drew from in her earlier novel, Torch); her divorce, infidelities, promiscuities, drug use, and staggering lack of preparation for the physical test of the PCT; her willingness to show you hers ​— ​and insist that she’s a worthy person anyway, goddammit ​— ​is offered without airbrush or saccharine. She sees no need for it. “People often think of honesty in opposition to kindness,” she told me. “I don’t.” She treats those who’ve sought her advice the same way. Funny and earnest, Sugar is a salve to snark.

We recently spoke about grief, empathy, writing, and the trio of hikers she dubbed the Three Young Bucks.

Here’s the transcript of our conversation:

I imagine it’s been crazy! You’ve been writing for years, and then one day Oprah calls and tells you she loves your book. And it’s being made into a movie. How does that feel?

Well, overwhelming and shocking and exciting. I feel so grateful and all of those things. But it really happened in this incremental way. Before Wild came out is when Reese Witherspoon optioned it. Then, as we moved toward the pub date in March, it was just everything good that can happen to a book was happening. The first week, it debuted at number seven on the New York Times best-seller list, which was just like, okay, I could die now, you know? Just that was so completely and utterly exciting because I’ve been writing long enough to know that that doesn’t always happen and a lot of really worthy books don’t become best-sellers. So then, Oprah didn’t make her announcement until June 1. She called me about a month after Wild had been out, but by the time she made her announcement, Wild had been out a few months and had already done better than anything I ever dreamed. It already had exceeded everything. It just kept getting better and more exciting. Thankfully it didn’t come all in one big whallop, you know? Like if Oprah and Reese and the book all came out in the same week, I probably would have had a heart attack … I had to drink a lot of champagne. There were so many different things to celebrate!

Ha! Right. So the story in Wild, even though your circumstances are so unique, it brings to mind the universal myth of the hero’s journey.

As I wrote Wild, I’m mindful of those ancient narratives, and you hope people will recognize themselves in your story, but you don’t know. Then the book comes out and people tell me what my book meant to them, so it’s like I get another view of my book. And I’ve been struck by how we live our lives so originally, yet the experiences we have are almost always universal. It’s the very things about which we feel we’re most alone, like grief or heartbreak or confusion or doubt, like for example that whole storyline where I love my first husband but I also want to leave him, I just remember at that time thinking, God, I am such a freak. What woman in her right mind would leave someone who is such a good man? You know? And turns out, there’s millions of them! So many people have written and said, I had that same thing in my relationship. Or my grief over my mother. So many people have written and said, you put words to what I feel. It’s a weird feeling: At this point, thousands of people have written to me and said, we have so much in common; my life is exactly like yours. What struck me is of course nobody’s life is exactly like mine and nobody’s life is exactly like yours, but the big experiences in our lives tend to be things that are experienced by many, many people … I think people saw, too, that I was really honest in terms of telling not just the pretty parts of my life, not just the heroic parts of who I am, but also the darker things. Everyone has messed up and everyone has risen to the occasion. Everyone has both positive and negative.

In Wild, there were a lot of parallels between what was going on with you physically and practically, and what was going on emotionally and spiritually. Monster, your backpack, was impossible to lift, and the things you were emotionally working through were pretty unbearable, too. Do you think that one makes the other more manageable in some way, or more understandable?

Yeah, some of those experiences, there’s a corollary between the physical and the emotional. Like when I’m really suffering, when it’s oh my god my feet are hurting, this is so hard, and I don’t know what I’m doing, that’s obviously really emblematic of that pain I was in and that confusion I had in my life. Some of it was when I crafted the book. I mean I didn’t write Wild because it was the biggest wilderness adventure and I’m the best hiker ever, you know? I told so much of my life in flashback, like, where does this backstory go? In some cases, I was actually thinking of it then. In my journal I wrote, I thought about my dad today or I cried. Other times it’s the writer’s craft, like okay, where am I going to tell you about my brother and I killing my mother’s horse? Where does that go? I had to ponder and feel intuitively, emotionally, where is the reader ready to hear it and where is the writer ready to tell it? I very intentionally was trying to build a sense of that connection between the internal world and the external world. In terms of the lived experience, that physical experience was so important in helping me figure out my emotional suffering. I was so focused on my emotions before my trip, and then I go on my hike, and it forces you to focus on your body. It wasn’t like I could sit around and dwell on how sad I felt — not to diminish those things; I had good reason to feel sad. But when you’re out there and you have to worry about getting water, it takes up that space in your mind, and that was such a good thing for me. To get out of your head.

Absolutely. So you brought up that scene where you and your brother had to shoot your mother’s horse. I read that peeking through my hands, it was just so evocative and gut-wrenching and hard to read. What did you do to be able to conjure some of those scenes so vividly from memory from so long ago?

Well, anyone who read that scene, even through their fingers, I’m like good for you because that’s the kind of scene I as a reader would skip! You know, I can’t read this — yet I had to write it. It was just the worst thing ever. I wrote that scene over and over. So in that case, that’s just emblazoned in my head forever. Also, I was an avid journal keeper, so I did go back and read what I’d written. But other things, sometimes I had my journals, but that’s the job of the memoirist, and that’s of course also where memoirists get in trouble! Memoir has one foot in the world of fiction, in terms of creating scenes that read like a novel, and then creating scenes that report what actually happened. And you do want to make a very serious effort to write what actually happened, do all you can to remember or research it. But also I just had to decide this is how I remember it and so I’m going to write it, with authority, knowing that the reader can say, well, this is her memory. When my brother read that scene, he was just devastated by it. He remembered it like that, too, but if he had written it, would he have pointed to slightly different things than me? Absolutely. That’s the thing with memoir, so you commit yourself to telling that story in a full-blown way, from the position of subjectivity. I’ve had really great experiences talking to people who are in the book, but it’s definitely like, okay, this is how I interpreted this person. It doesn’t mean that’s who that person is; just how that person was to me. Like the Three Young Bucks, these handsome guys I had a crush on? An old man would have a different take on them! It’s so funny; speaking of the Three Young Bucks, one of them wrote me after reading Wild, and he was like, I just want to say, thank you for your accurate portrayal of us because being handsome and studly is exactly how I remember myself.

Oh that’s great! I love it.

Yeah. So part of being a writer is you really are working your memory all the time … you think you don’t remember much and you start writing, and more comes back. It’s like running into an old friend: You start talking about old times, and in the course of your conversation, you remember things you’d thought you’d forgotten. … That happened to me a lot in Wild. Once you get into it, you can retrieve more memory, and the emotional feeling of the experience.

So much of your work deals with or makes reference to your mother’s death, your grief around that. Your novel Torch is about a mom dying very suddenly of cancer — it’s reminiscent of the real story that you reveal in Wild. Did you need to write the fictionalized version before you could write Wild? How did writing about it help you work through the grief?

It never occurred to me to write Wild until I did. I thought of myself primarily as a fiction writer so … I wrote a novel. But also I didn’t want to tell, I wasn’t interested for whatever reason, maybe I wasn’t ready, to tell my individual true story of my grief. … I did take the situation and the setting, my mom dies young of cancer and this family kind of explodes, and based the novel on that. … Torch was like this burning story that I had, and it felt really important to me that it not be just the story of me, or one young woman, that it was a family — the only way I can explain it is I just was so driven to write that book. Then … after I finished Torch and was sort of casting about for what to do next, Wild just sort of came up. I was going to write an essay about the experience, the hike. I thought, I have enough material for an essay and started writing. And it became a book. There are things in Torch and in Wild that echo each other and in some cases are almost identical because in Torch I was drawing on real life and in Wild I was writing about real life. And in the Dear Sugar book, Tiny Beautiful Things, those columns, too, I tell stories about my mom’s death and my grief. I just think obviously it’s been the defining, a really defining experience in my life and something I’ve been obsessed with as a writer. When I teach writing I always say: Trust the heat; write what you feel driven to write about even if you feel embarrassed. And I do feel a little bit like, okay, come on, you know, get over it. But then all these people tell me how much my work meant to them about their own grief. I will say what’s interesting to me now is I feel like in some ways — I mean I’m sure I’ll write about my mom’s death and my grief throughout my whole life, I’m sure it will come up in different ways — but I do feel a bit released from it as a writer. The next couple books I have in mind, that’s not going to be there at all in some cases. I’m writing a novel now, and there are no dead mothers. At least so far, knock on wood! One will probably pop up at some point. It’s interesting. I think you just have to write what you’re obsessed with.

You changed your last name to Strayed at a pretty rough time in your life. I wonder what the word meant to you then, and if it’s changed, and if it still feels like it fits?

Yeah, it really feels like it fits, more than ever. I think some people equate “strayed” with being lost, and I never did. I always saw it as a positive thing, as taking an alternative route — stepped off the path. And I just felt so alone then. I felt like I didn’t have a family, and I was getting divorced, I was so young, like who’s divorced by age 26? I felt all these things like I was taking a different route. So in some ways it expressed who I was, and a “stray” is someone who doesn’t have a mother or a father, so the definition of that word was kind of an affirmation to me. But more importantly, the act of naming myself was a powerful and positive step for me where I was saying, okay, I don’t have a family; I have to kind of make my own life — we all have to make our own lives, but the fact that I had to was incredibly stark and clear to me at that time. I didn’t have parents to fall back on, and so it was a powerful act about making my own life and in some ways creating my own family and my own heritage and sort of moving into the future. Now, yeah that’s the danger; we go through these phases, and you’re in your twenties, and you’re like, no, my name is, you know, Appleblossom. It’s easy to mock that sort of thing … but I was dead serious. It just feels really like my name. I feel as bound to it as if my grandfathers and [grand]mothers before me had that name. So I love it, I’ve really loved it from the beginning, and I’ve settled into it and love it even more than I did at the beginning.

That’s great. So you mentioned Tiny Beautiful Things. As a working writer, what motivated you to take on that non-paying, anonymous job [as Dear Sugar]?

I know; “job” is a generous term for it! It was really just my gut feeling that it would be interesting and fun. I did it on a lark at first. I thought, oh, its just a little thing I can do, and then of course I got deep into it and was like, wow, I’m really going to put my all into this, and it wasn’t going to be in any way a lesser form of writing. I was gonna write the best I could with the most intelligence and ferocity and heart and all those things that I could muster the same way that I would in fiction or memoir. I just gave it everything … I just had a gut feeling that I should do it.

Your work as Sugar has been described as full of “radical empathy.” So here’s a chicken or egg kind of question: Do you have to have deep empathy to be a good writer, or does working on your writing cause you to develop empathy? Does one feed the other?

Yeah, I think if you have empathy, it makes you a better writer. In the writers I love, there’s always a deep generous compassion at the heart of it. To be witty and snarky is amusing and entertaining, but ultimately when you read something that’s snarky and kind of cutting, you laugh but you feel kinda icky afterwards. The work you read and it actually kind of fills your soul, like it nourishes you, that’s always what I’ve wanted to do as a writer. It wasn’t like with Sugar I thought, I’m going try this thing on and be really kind to everyone. I was writing, from a true place, what I think of their problem. And I also felt my power. It’s a really vulnerable thing to write anonymously to a stranger. Some of these letters, they’ve never even told anyone about that thing. And they’re taking the chance of writing to me, and I wasn’t going to reply condemning them and humiliating them. Even when I was telling them hard things, challenging their assumptions, I always try to be as gentle as I possibly could while telling the truth. I think often people think of honesty in opposition to kindness, and I don’t. I think you can be honest and really affirming and loving at the same time. In the Sugar letters, a lot I’ll say, look, you’re thinking wrong about this, but it’s okay; you’re not alone; a lot of us make these same mistakes. Which is why I told stories from my own life, because it was like look, I’ve been there, too, or this is kind of like that. It’s using narrative instead of just condemning or guiding or bossing.

One of the criticisms that gets lobbed at memoir is that it’s narcissistic. And it can be. What’s the trick to making personal stories feel universal instead?

That whole “memoir is narcissistic” thing, I get so tired of that. ‘Cause you’re right; it can be. Just like poetry can be and fiction can be. Are there bad memoirs? Of course, but there are no more bad memoirs than bad books of poetry or novels. The people who disregard the whole genre? They don’t know the form; they haven’t read enough work. Writing about yourself, when you do it well, it’s the opposite of narcissism; it’s the opposite of navel-gazing. It’s really taking the chance, really trying to reveal a huge amount of your own humanity, to show the dark side, the complicated side, the contradictory side, the light side, and to just say here I am, you know? And I’m complex like you … I’ve heard people criticize Dear Sugar on those grounds like, oh, every time someone asks her for advice, she turns it back to herself. And I think well, okay, if you think that, you’re just not getting what I’m doing. Because I’m not using those stories that way; I’m always bringing it back to that letter-writer — using narrative, using storytelling to essentially illuminate the human condition, using it specifically to illuminate that one specific situation that’s been presented to me. It’s the best way I can think of to do it as a writer. And I do think it’s a really effective way. Every time I’ve been heartbroken or had any kind of trouble, I turn to books. I read stories that are like mine. I read essays that speak to my experience, or I read poetry, and those things are a consolation, and so I’m trying to offer that through Sugar.

Your writing has been described as fearless. I wonder for writers, but for anybody, struggling with that point where you have a choice—you can be totally honest and pretty vulnerable or you can hold back and feel safer—what advice do you have?

The first thing you should do is just don’t hold back. The thing we forget when we’re first writing something is there isn’t a portal that goes directly from your computer to The New Yorker, right?

Sadly, no.

Not like it’s instantly going to be published right off the bat, so I say the important thing is to be fearless in the creation. To really take those risks because as I was saying when it comes to memory, one thing leads to another and that leads you deeper still. I think emotional risk-taking does the same thing. You write about something that scares you, and it leads you to other things, and in that process, you might find that thing you were so scared of doesn’t even need to be there. You can pull back; you can keep it in a way that’s both risky but also somewhat comfortable. So first create fearlessly, then make decisions. I think, too, part of being a writer is being uncomfortable. If I saw you right now in a hotel lobby reading my book, my stomach would turn ’cause I’d be like, oh, what does she think of my book? We’re vulnerable. I’ve written this thing, and you’re reading it, and you get to have your opinion about it, and that’s scary for all these different reasons. Because it matters. If it didn’t matter, you probably shouldn’t be doing it. I think part of the deal when you sign up to be a writer is to constantly put yourself outside of that comfort zone.


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