Best of Design Matters: Cheryl Strayed

Cheryl Strayed battled through remarkable adversity—and the most intense of hikes—to emerge as one of the best American writers working today.

Cheryl Strayed battled through remarkable adversity—and the most intense of hikes—to emerge as one of the best American writers working today.

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Cheryl Strayed:

And, it’s funny as I say these words, the female in me, the woman who was raised as a girl is like, “Oh, don’t say that. Don’t say you want to be a great American writer.”

Speaker 1:

This is Design Matters, with Debbie Millman.

Speaker 1:

On this episode, Debbie talks with writer, Cheryl Strayed, about her childhood, her career, and about the value of taking a very long hike.

Cheryl Strayed:

What happens on the outside, one foot in front of the other in front of the other, also happens on the inside. The way to heal anything is to keep going.

Speaker 1:

Here’s Debbie.

Debbie Millman:

You could say that Cheryl Strayed is very adaptable. Her memoir, Wild, was adapted into a movie starring Reese Witherspoon, another book, Tiny, Beautiful Things, was adapted for the stage by Nia Vardalos and Thomas Kail. Tiny Beautiful Things, itself, was adapted from an advice column she once wrote called, Dear Sugar. And that advice column has ultimately been adapted into a New York Times podcast, called Sugar Calling. To talk about it all, I’m joined by Cheryl Strayed, who is recording herself in her home in Portland, Oregon. Cheryl Strayed, welcome to Design Matters.

Cheryl Strayed:

Hi, Debbie. I am so thrilled to be here. I’m a fan of the podcast and I’ve been dying to talk to you for ages.

Debbie Millman:

Oh, I’m so glad, I’m so excited. I understand that you’re socially isolating in Portland with your husband, Brian, and your two teenagers, one of whom just had a 16th birthday.

Cheryl Strayed:

Yes.

Debbie Millman:

How are you all doing?

Cheryl Strayed:

First of all, we’re doing great, and we’re so lucky to have each other, and to have our health, and to be secure, and safe, and all of that. And yet, and yet-

Debbie Millman:

And yet.

Cheryl Strayed:

There are challenges. The teenage years, as you know, are meant to be times when the kids are socially distancing from their parents. It’s when they’re like… They don’t want to only be in the house with us all the time. And, so I feel for them. And everything fun on her horizon has been canceled. So, we’re having to think of new fun things. And the teenagers have a different idea of fun than the adults do, it turns out.

Debbie Millman:

I listened to a recent podcast where you said that this pandemic has made it clear to you that the first thing you are is a writer. Was that ever really in doubt?

Cheryl Strayed:

No. No. It was never in doubt inside myself. But, what I meant by that is, one of the things that happened after Wild became a bestseller, is suddenly I had so many opportunities that were not writing, they were writing-adjacent. For example, I now have a really active career as a paid public speaker. I never… I mean, I do unpaid public talks too. But what I mean is I never in my wildest dreams imagined that I would be traveling the world giving talks, and I am. I actually have a whole career of that, in addition to my writing. And that was borne out of a combination of Wild’s success, and then also my, much to my surprise, I’m good at it and I enjoy it.

Cheryl Strayed:

And so, it got really easy to say yes to talks and, “Yes, I’ll go there, and yes, I’ll do this.” I say no to a lot, too, but it became this thing I could do to earn money, and to feel like I was doing interesting and important work in the world. That in some ways would be, not a replacement for my writing, but sometimes a little easier. It’d be like, “Oops, I can’t write today because I have to fly to Dallas to give a talk or something.” And that has been taken away now with this pandemic. All of my public engagements have been canceled. And, I know I’m not alone in that. Other writers who give talks of that experience, too. So, it’s like, “Oh, okay. Back to my origins. I’m just going to write my way out of this.”

Debbie Millman:

I understand that you’re huge planner, as am I, and it’s been hard for you not to know what you’re doing next month or July or August. How are you managing your schedule? And I’m mostly asking this for my own sake, to really get a sense of how you’re managing.

Cheryl Strayed:

It’s really interesting, isn’t it? I mean, for me, I’ve realized that planning has always made me feel safe, and it’s always been, for me, the vehicle of my ambitions. What I mean by that is, that setting intentions has always been really important for me in terms of if I’m in a place, whether it be emotionally or professionally or financially, that is not a good place I think, “Okay. My intention is to go there.” And I make a plan and I see it on the horizon, and I think about the steps I need to take to get there. And so on the deepest level, planning has been actually an incredibly healing act for me. It’s also been, just I get pleasure from knowing the logistics of everything. I’m a detailed person. I love maybe that sense of control that I have when I look at my calendar and I go, “Okay. We’re going to do this in June, and that in July, and that in August. And this time next year we’ll be here.”

Cheryl Strayed:

And I love that. It gives me a kind of pleasure. I mean, I even joke with my husband. Our long-running argument. So, let’s see. We met in 1995. So I guess it’ll be 25 years since we met this fall, this September. My running joke with him, we’ve been fighting for decades about him not putting things on the calendar and not being a planner. And then, every once in a while, he’ll do it, he’ll put something on the calendar and I’m like, “That is the sexiest thing you ever did for me.”

Debbie Millman:

Yeah. Yeah. I totally get it.

Cheryl Strayed:

That’s my love language.

Debbie Millman:

Yeah, absolutely.

Cheryl Strayed:

What about you?

Debbie Millman:

Well, I know that you’re a list maker, and you’re not only a list maker, but you make sub-lists to your lists, and I do the same thing.

Cheryl Strayed:

Of course.

Debbie Millman:

And I am so, I don’t know what the word would be, attached to my calendar. I have a paper calendar. I’ve had a paper calendar for decades. And, my dad used to send me the American Express Book Calendar, which I used to use. And then he passed away, so I needed another vehicle. And so I just have this little paper calendar. It’s actually little, but it’s a two-year calendar. And I am attached to this thing. It goes with me everywhere. When Roxanne and I were in Italy over last summer, I left it in the hotel, one of our hotel rooms, and didn’t realize it until we were hours away. And I was inconsolable.

Debbie Millman:

I mean, it was almost like, “Okay, we need to go home,” because of my calendar not being there. She actually was able to get it for me. She’s the most amazing human on the planet. She actually was able to call the hotel, get the planner from the room, and have it sent to me at our next hotel. And she actually said it’s because she’s nice to the cleaning people in the hotel, and I think that’s true, which is why they sent it to us, why they found it and sent it to us. But, I am also-

Cheryl Strayed:

Well, you know, hotels do that, Debbie.

Debbie Millman:

Not the hotels I used to go to. It’s a different world with Roxanne.

Cheryl Strayed:

It is. She opens doors. Well, I’m a big fan of Roxanne as well. But I have to tell you, you’re speaking to a real kindred spirit here about this, because I know that feeling, too. I think that you felt untethered and lost without that. It feels like the thing that anchors me to my life. And even though I know rationally, we don’t have control of what’s to come-

Debbie Millman:

It’s some semblance.

Cheryl Strayed:

… I like-

Debbie Millman:

Yeah.

Cheryl Strayed:

… Yeah. I like kind of feeling like I can. And I think, so I didn’t even answer your question. So, how am I dealing with it? The first thing, I was kind of in denial, like a lot of people. What I decided, is the pandemic would last about eight weeks. At least its impact on my life would be… That was the first thing like, “Okay, everything is canceled in March and April and maybe May, but June and July and August are totally on.”

Cheryl Strayed:

And then, as the weeks passed and I realized, “Oh, my gosh,” and I finally, I had to do the thing I have many times advised others to do when they feel powerless, is to surrender, and to accept. That’s about accepting what’s true. Accepting what’s true. Really, one of the most radical acts of my life, and I think any life, even if what’s true isn’t what you want to be true.

Debbie Millman:

Right.

Cheryl Strayed:

Because then you can work from a place of reality, rather than delusion. And so I’m trying to accept it and let go the future, or at least my sense of knowing what’s going to happen in the future.

Debbie Millman:

Let’s go into the past a little bit. I’d love to talk to you a little bit about how you have navigated the arc of your life. You were born Cheryl Nyland in Spangler, Pennsylvania, and moved to Chaska, Minnesota when you were six years old. Shortly thereafter, your parents got divorced. And, in addition to the time after your Mother died, it seems as if those years were some of the darkest years of your life. Did you realize it at the time?

Cheryl Strayed:

Gosh, that’s such a great question. I did realize it to the extent that a child can, which is somewhat limited. I was born into a house of really extremes. On one hand, I had this Mother who was very loving and very kind-hearted, and warm, and optimistic. And, in so many ways communicated to me and my older, I have an older sister who’s three years older and a younger brother who’s about three years younger. And she always communicated to us that sense of wonder, and love, and light, and the beautiful things. But we were living in a house that was frankly, terrifying. My Father was violent and abusive. He was emotionally abusive to all of us. He was physically violent to my Mother, to an extreme degree. And, we were terrified of him. And also, we witnessed, I witnessed, my brother and sister and I all witnessed, horrifying things. Things that I never witnessed beyond that as an adult.

Cheryl Strayed:

I mean, so as a little child, some of the first things I saw were really, my Mother being beat beaten by my Father, my Mother almost been killed before my eyes by my Father. My Mother being raped by my Father. And so, my perception of what I understood in those years is definitely one of fear, and sorrow, and terror, and darkness. But, because that was my life, it wasn’t really until my Mother finally escaped my Dad that I realized, “Oh, this is what happiness is. This is how it should be.” So yeah, I mean, I really think I had these kind of two childhoods, really three childhoods, but the first one was terror, and darkness, and violence, and abuse. And the second one was my Mom is a single Mom, and we were very poor. We were poor with my Dad too, but really living in poverty with a single Mom and three kids, and a lot of chaos and disarray, but also a lot of light, and joy, and fun. And no longer being under the sort of weight of that fear that you have when you live with somebody who’s abusive.

Debbie Millman:

I completely understand. In many ways I had a lot of similar experiences. So, a lot of the questions I’m going to ask you are really not only for my listeners’ benefit, but also for my own, in terms of really being so curious about how somebody can emerge from that kind of darkness to be able to say, “This is happiness. This is happiness.” You’ve written this about what a father’s role is in his children’s life. “The father’s job is to teach his children how to be warriors. To give them the confidence to get on the horse, to ride into battle when it’s necessary to do so. If you don’t get that from your father, you have to teach yourself.” That so resonated with me. What do you think you had to teach yourself? What is the biggest thing you think you had to teach yourself?

Cheryl Strayed:

Oh, you don’t ask little questions, do you? You ask big questions. Big questions.

Debbie Millman:

Sorry.

Cheryl Strayed:

Big questions. I think that the biggest thing is that I’m okay in this world. I have the strength, and the courage, and the resilience, and the heart to be okay to be safe within myself. And, I think that, that’s what I mean when I said, “To be a warrior.” I mean, I think we very often think of this in terms of battle. And, years ago I wrote about this in Wild, too. So right after my Mom died, I was living in Minneapolis. I was 22. And a friend of mine gave me a gift certificate to see an astrologer. And I was like, “Okay, well, I don’t know, like, ah, what’s this astrology stuff? But I thought, “Okay, I’ll go.” And I went and I talked to this woman, Pat Kaluza, and she had this hippie sort of place in Minneapolis, and she read my birth chart. And it was astounding and amazing.

Cheryl Strayed:

And, one of the things she said to me, she kept going to the father. She kept saying, “Your Father, he’s a Vietnam Vet, or he’s troubled, or he’s,” and I kept saying like, “Oh, yeah. My Father’s not in my life. He’s nothing, he’s nothing. He’s not anything.” And she said to me, “Well, you were wounded. Your father was wounded. And when you have a parent who’s wounded, who hasn’t healed his or her wounds, you as the child, you’re wounded in the same place. And so you’re going to have to heal that wound.” And the way she talked to me about it is that there will be times in your life that you need to ride into battle for yourself, and you need to teach yourself how to do that.

Cheryl Strayed:

And, I would say that that extends beyond necessarily the father. I think that if we didn’t get that essential sense of self-worth from both parents, we need to reckon with that in our adult lives. And so, with my Father, I had to heal many things, but the biggest one, you asked what the most important one, I think it was that sense is that I’m secure and safe in the world, and that I’m strong enough to face anything, really. And, to really step into that knowledge, not that you’ll be always brave, or always do the right thing, or always accept what’s happening in a graceful way or courageous way. But that at my deepest, deepest, deepest place within me, I believe in the power of my own resilience, and ability to survive and persist. And I think that’s what the parents give us, if they love us well, and they love us right. And if we don’t get that, we have to find it ourselves in the world.

Debbie Millman:

I think that as I was re-reading Wild, and as I watched the movie again too, which was really wonderful, I also got the sense that your journey was one of finding out if you could rely on yourself, if you could take care of yourself. Pretty extreme way of testing yourself, but I got the sense that that ability to do that was also underneath everything else that you were doing.

Cheryl Strayed:

I think so, too. And I want to say too, I think that we all need to do that. Obviously, somebody like me who had a Father who was abusive and not the Father that anyone wants. And then a Mother who died. I was really an orphan, and I had to go and find those things, as you say. And yet I think part of maybe the human journey is that. I even think of my own kids, teenagers right now, who are loved, and secure, and living in a very happy home, and have wonderful lives. And yet, what I know about them, is that that part of their journey is going to be finding their way, and finding their strength, and finding their courage, and also finding their path. And all of those things are made more difficult when we have difficult parents, or dead parents, or abusive parents, but they’re all… It’s part of what we have to do as humans.

Cheryl Strayed:

And that’s why I think so often, it wasn’t until after I actually wrote Wild that I understood what I had done on that hike, is that I’d given myself my own rite of passage.

Debbie Millman:

Absolutely.

Cheryl Strayed:

That I’d said, “You have to go test yourself to see who you are.” And that’s those rituals of rites of passage are what we’ve done as humans throughout all time, across every culture, and continent, and so on and so forth. We don’t do that so much anymore and I think it’s a loss. I think most of us would benefit from being asked to find out who we really are, by being put in uncomfortable circumstances or challenging circumstances.

Debbie Millman:

When I was doing my research on your childhood and adolescence, I came across a couple of little facts that really were wonderfully surprising. I know that when you were 13, you moved to Aiken County. It was very rural, you lived in a house with your Mom and your Stepfather. They built the house, and for many years, the house didn’t have electricity or running water, didn’t have indoor plumbing until after you went to college. But despite all of this, Cheryl Strayed, you were a high school cheerleader and the Homecoming Queen. You were an overachiever from like day one.

Cheryl Strayed:

Uh-huh (affirmative), I was. I was.

Speaker 2:

So you were very popular in high school? I was not a cheerleader or a Homecoming Queen, and really, really looked up to the girls that were. So, were you very popular? Were you somebody that was just the belle of the ball?

Cheryl Strayed:

So let me explain. My Stepfather, who was a carpenter, he was seven years younger than my Mom. They married when I was 11, and he was working under the table for this roofing contractor. And, it was the middle of the winter in Minnesota, there was ice on the roof. He slid off the roof and broke his back. And, as I said, we were always flat broke. And, he was injured and out of work for more than a year. And my Mom at the time was working as an administrative assistant for this small town attorney in Chaska, Minnesota. And he said, “I’ll represent you pro bono. It’s not fair.” Because my stepfather was working under the table his boss said, “Oh, no. I don’t need to pay you anything.”

Cheryl Strayed:

So, by the end of the year, they got a $12,000 check. That was the payment for a broken back, back in 1980 or so. And, my Mom said, “This is our only chance we’ll ever have our own home that we own. And let’s not buy a home, let’s buy land.” So they went to Northern Minnesota, yeah. And we moved to 40 acres of land. We lived really in a tarpaper shack, a one-room tarpaper shack, for the first six months and we built the house ourselves. And, it was a lot of work, and it was incredibly difficult, and I was a teenager. And I wanted to be pretty, and popular, and not associated with going to the bathroom in an outhouse, or taking a bath in a pond, which is what I did. Or, taking a bath in a bucket, which is what I did.

Cheryl Strayed:

So yeah. My rebellion in my teen years was to seem to be a version of myself, that I wanted to project sense of success, and grace, and togetherness. And I wanted to be popular, because to be popular is to be loved. I wanted people to love me. And I should say, the town. I went to school in at McGregor High School. It’s a very small school. So being popular there, being the cheerleader there, it’s a different thing than… Some people went to these big schools and it’s a whole other level of stuff. But, I was just in this little podunk school, and yeah, I made myself loved.

Debbie Millman:

Now let’s talk a little bit about books, because you’ve written about how, as you were growing up, books were your religion. And you’ve cited the experience of reading Dalton Trumbo’s novel, Johnny Got His Gun. It’s a book that first exposed you to the power of inhabiting the life of another human.

Cheryl Strayed:

Yeah.

Debbie Millman:

What was that like for you? How did that infuse who you were?

Cheryl Strayed:

Have you read that book?

Debbie Millman:

I have not. I have not. The book that did that for me was Ernest Hemingway’s, The Old Man and the Sea, which I still remember reading in seventh grade, just feeling the power of that experience.

Cheryl Strayed:

Yeah. I had that experience with Hemingway, too, right around eighth or ninth grade in his short story, In Another Country. And so, Johnny Got His Gun, Dalton Trumbo, really, really powerfully important book. I think I was about 14 when I read it. And, it’s just, you’re inside the mind of a man who’s been deeply injured in the war, and lost his limbs, and you’re just living in his head, and having his memories, and his delusions, and his sorrows, and his rages. And you’re right there inside of him. And I think it was maybe the first book that the material was so utterly dark, and painful, and true. That it was the first time that I understood what war was, what grief was. I’d learned about things from a distance, and what that novel taught me is how you can inhabit an experience that is so not your own.

Cheryl Strayed:

And, I loved books long before that, but that was the first time I stepped into one and thought, “This-

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Cheryl Strayed:

But that was the first time I stepped into one and thought this is a kind of magic, if you will. This is a kind of portal that I guess I’ve been longing to enter for a long time. Another piece of this that goes way back is always as a young child, I always wanted to know what was happening inside of other people’s minds. Like really. What did they really feel? What did they really think? What was their actual experience of being human? And so in Dalton Trumbo’s book, I was like, “Wow, I’ve finally been let in to that secret.”

Debbie:

You’ve also said that your sexuality was shaped by the Victorian era erotic classic The Pearl which is a compilation of serialized porn stories. And you stole it from your mom when you were a teenager. I still have The Godfather and The Crazy Ladies from my parents.

Cheryl Strayed:

Oh my God. No, trust me. The Pearl is so beyond any of that.

Debbie:

You said this here that it was horribly dirty.

Cheryl Strayed:

Like all the Pearl is… No it’s… And that’s all it is. I mean it’s actually pornography. It’s Victorian pornography and it was actually in existence in England. It was these sort of, I guess, early days zines that were passed around. And it had sat on my mother’s bookshelf for, really, I think years before I noticed it. And suddenly when I was like 13 or 14, I found it and this is how I learned everything. That’s how I learned how to masturbate. And I mean, I read it all. I read it so much that the book really actually fell apart and it was just a stack of papers. But it’s so unbelievably dirty and you can still buy this book to this day. It’s still in print and it’s really astonishing. It’s like all of these unbelievable things that people do to each other. If you ever wonder if smut is like a modern day invention, go read The Pearl and you’ll learn otherwise.

Debbie:

You also started working at 13. You had a variety of jobs. You were a janitor’s assistant at your high school waxing floors. You were a waitress at the Dairy Queen. And I understand you can put a curl on the top of a soft serve ice cream cone like a pro.

Cheryl Strayed:

Of course. I worked there. So yeah, I mean, that’s the thing growing up poor, what you quickly realize is if you ever want anything, you have to earn the money yourself. Because even though my mom provided for us to the best of her abilities, I wanted things like brand name shoes or Levi jeans. We would go to Kmart and at the beginning of the school year and we’d each get a certain amount of money we could spend. And then that was it. And I was like, “I don’t want to buy… I want to wear the brands.” And my mom would say, “I can’t afford it.” So as soon as I could… I babysat before that. But honestly, as soon as I could, I got myself a job.

Cheryl Strayed:

And I was like 13 and a half. I sort of fudged my age. I think you had to be 14 to actually work. But by 13, I worked a full time job as a janitor’s assistant in my school cleaning the books, the shelves and the drawers and the desk, getting gum off of things and painting. It was through this program for low income kids. I worked and I earned my money and I bought my stuff. That was part of the whole plan that I would get it myself if it couldn’t be provided for me. Sometimes I talked to my peers who were going to camp or going to Paris or whatever and I envy them.

Cheryl Strayed:

And yet I also think, “Wow, the best education I ever had was being a janitor in my high school.” And then going from that job straight to my job at the Dairy Queen. There was a half hour between those jobs. I would work from 7:00 AM to 3:30 PM as the janitor’s assistant. And then I would walk across town to start my 4:00 PM shift at the Dairy Queen that went until 10:30 PM. I still remember that schedule. And I did that all summer and they were minimum wage jobs but they were the first lesson I had in really how to be self-sufficient and making it happen. Like not expecting others to make it happen for you. And I treasure that. I think I learned more doing that than I would have going to a lovely summer camp, but we all learned. We all find our way.

Debbie:

I read that it never occurred to you to attend college outside of Minnesota. And you only applied to one school, the University of St. Thomas in St. Paul. How come? How come it didn’t occur to you that you could go out outside of Minnesota?

Cheryl Strayed:

It never occurred to me. It absolutely never occurred to me that it was possible to leave my state to go to college. Like to me, the furthest even going to college seemed like going very far away. And I’ll loop back to answer your question, how come, in a minute. But I just want to say, I remember the first time that I actually went to Harvard and walked around the campus. I was in graduate school. I was probably 30 and my essay Heroin/e had been selected for Best American Essays. And they had me come to Cambridge to do an event launching that book because my essay was in it. And I did this reading and then walked around campus. Harvard. I was like, “I’m right by Harvard. I’m just going to go look.” And I walked around there and I was overwhelmed with emotion.

Cheryl Strayed:

I mean, I was just… I felt it was like I had been struck in the head and I was just looking around in wonder, but also sorrow and in a kind of anger, because what I realized is that it’s a good thing I didn’t know that I could have gone to school outside of Minnesota. Because if I had gone to someplace like Harvard straight out of my little Podunk town, straight out of the life that I… the childhood I’d had and the life I’d led, it would have been like sending me to like a different con… I mean, it’s a different world. And it was just, all I can say, is when you are living in a certain environment among a certain community with certain values and certain ideas about what city people are, what educated people are, it didn’t… the big dream wasn’t like, “Let’s get our kids to Harvard and Yale.”

Cheryl Strayed:

Like I never… Those don’t even seem like real places to me. They seemed like places in a Trixie Belden book or something.

Debbie:

Trixie Belden.

Cheryl Strayed:

I love Trixie Belden.

Debbie:

Honey. Her friend, honey.

Cheryl Strayed:

I know. I love Honey.

Debbie:

I love Honey.

Cheryl Strayed:

So for me it was like okay… but so the furthest I could go is to college. And the reason I didn’t know to apply to more than one is because nobody told me. I wasn’t folded into anyone’s arms when it came to like, “Well, let’s talk about college. Let’s talk about your options. Let’s talk about the process.” I figured out by reading something that I had to take the ACT test. Nobody talked to me about it. I paid for it myself. I drove myself there. I took the test. I didn’t study for it because I was told you can’t study for that test. You just go and it’s like an aptitude test. I don’t know what score I got because it didn’t even matter to me. I just took the test and did my best. And I went to… I put in my application to one school and I applied to this one school because it was a small school. I was overwhelmed of thinking like going to the University of Minnesota. It just seemed too big.

Cheryl Strayed:

So yeah, I look back on it and think, “What was I thinking?” And all I can say is I just didn’t have that information available. And I think we think this is so unique, but it’s not. I mean it’s the reality for a lot of kids living in poverty that they don’t know the way to college. I think there are more programs in place now for people like me, but there weren’t then. I do remember my guidance counselor one time when I was maybe a junior, I had taken some state mandated, standardized test and I had done mediocre on the math portion, but on the verbal portion I gotten like 98% or 99%. I do remember he called me into his office and he said, “We were all really shocked by your score on this. You scored better than almost everyone who took this test.” And I remember thinking the only one who wasn’t surprised was me.

Debbie:

You showed them.

Cheryl Strayed:

Yeah. But you know, I didn’t say, “What do you mean you’re surprised?” I mean…

Debbie:

Yeah. You accepted his surprises.

Cheryl Strayed:

In some ways it was… It’s about that being the homecoming queen. I hid my intelligence. I buried my brains under a rock even though they were there. So that test revealed who I really was, but I didn’t kind of show that in the world until later.

Debbie:

For your sophomore year, you transferred to the University of Minnesota in Minneapolis and you studied english and women’s studies. What did you think you wanted to do professionally at that point?

Cheryl Strayed:

As a poor kid getting an education the first goal, and really at first the only goal, was like you get a job so you can make money. And I first thought that the only path to that would be journalism. So when I was a freshman, I majored in journalism. And when I transferred to the University of Minnesota, I was like “Journalism.” But I… I took a class, really in that first year or so, with Michael Dennis Brown, the poet Michael Dennis Brown, and my eyes. I just… Everything… Absolutely exploded. And I thought I have to trust this. I have to.

Cheryl Strayed:

I thought that I could sort of funnel my desire to write into the channel of journalism because it’s the job that you can actually get paid to write. But I don’t want to do that. I want to really put all of my heart and my faith in creative writing. So I switched majors and became an English major. And what I thought I’d do with that is become a great American writer. That’s what I thought I’d do with it. I was absolutely relentlessly ruthlessly committed to following through and being just really, really holding hard onto that thread that was my writing and doing it and doing it and doing it until I succeeded.

Cheryl Strayed:

And you know, it’s funny, as I say these words the female in me, the woman who was raised as a girl was like, “Oh, don’t say that. Don’t say you want to be a great American writer, because that seems cocky or that you’re bragging, or…” But I’ll tell you like that’s the thing that got me through is that like, again, the intention, the plan, the ambition. If I sort of dithered around and said, “Well, you know, I hope that this turns out and I hope I can publish a story.” I would never, ever, ever be talking to you right now. I had to just be an absolute relentless warrior and a motherfucker on behalf of my own self as a writer.

Debbie:

Write like a motherfucker, right?

Cheryl Strayed:

That’s right.

Debbie:

It reminds me…

Cheryl Strayed:

I mean that’s right.

Debbie:

Yeah. And it reminds me of that little mantra you had while you were on your hike. “I’m not afraid. I’m not afraid. I will not be afraid.”

Cheryl Strayed:

Yeah. Well, and of course, when did I say “I’m not afraid?” When I was.

Debbie:

When you were. Yeah.

Cheryl Strayed:

And you know, even to this day writing is so hard for me. It’s so hard for me. And I still have to be a warrior and a motherfucker. I still have to say, “Cheryl, you can do this. You’re going to do this. And you are not going to give up. You’re not going to be second. You’re going to go. You’re going to go all the way to the finish line.” And so it’s a part of that… Back then… And of course the women’s studies piece, I was a double major, is that I am a feminist and I have always been a feminist ever since I learned the word when I was five or six. And I just loved centering feminism in my… when it came to my education, higher learning.

Debbie:

In March of 1991 when your mom was 45, you were 22, your mom died of cancer. And you’ve said that your mother’s death was in many ways your Genesis story and the start of what you called your wild years. And you said that for you using drugs or having a lot of sex or any sort of reckless behavior was about love. Was about trying to find love in this weird way, trying to show the world this woman’s life meant so much that I’m going to ruin mine to honor her. And I wanted to ask you about that destructive thing that we do. Why do you think we hurt ourselves when we’re hurt?

Cheryl Strayed:

Wow. Again, you with the big questions, Debbie.

Debbie:

I kind of want to say, “I’m sorry,” but I’m like, “Sorry, not sorry.”

Cheryl Strayed:

So it’s so deep and so big and layered the answers. Why do we hurt ourselves when we’re suffering? Why do we self-destruct when we feel like we’ve been ruined? I think it’s a couple of things. I think one of the things is it’s a signal. It’s a signal to the people around us that we’re saying, “Help me.” Even if we, with our words, are saying like, “Oh no, I’m fine. Just leave me alone.” I mean and in so many ways, that’s when you turn to drugs, for example, that’s a way of pushing others away from you. And yet what I was so clearly trying to do, I can see, is to be like, “Help me, help me, help me.” And it’s also a kind of test. So it’s a signal, “I need help.” It’s a test. Is there anyone out there who loves me enough to help me?

Cheryl Strayed:

I also think, in my case, there was this sort of division within me or this polarity that was the… that’s almost like mythic in its… When I think about it and when I interpret it this way is like the mother, the good mother who’s been taken from me and the bad father, the dark father who abandoned me. If I can’t be the woman my mother raised me to be, that ambitious, generous life, light-filled person, maybe I can be the junk, the pile of shit, the darkness, that my father nurtured in me. There was something that I had to figure out about those primal relationships that I had to rage against and heal and understand and revise. And I think that a lot of us have to do that.

Cheryl Strayed:

I think that a lot of people who are suffering and certainly people who’ve written to me as Sugar, they have a problem. They write with the problem. They’re like, “This is my question. This is my thing.” But really the problem is that deep, deep river that’s flowing beneath all the troubles, that subterranean channel that is your parents, that is those early stories you received, your losses and your gains and your wounds and your sorrows that you have to heal them. And sometimes healing is an ugly thing. Sometimes healing is destruction. Sometimes healing is turning away. Sometimes healing is a kind of rage and anger and I think that for me, it was just like I had to pass through everything. So the image that always comes to mind to me is one of total destruction. When I saw that I was going to lose everything after my mom died, and I did, my family also really fell apart and was lost.

Cheryl Strayed:

When I understood that that was what was going to happen and that I couldn’t make it not happen, that’s when I really turned to heroin. That’s when I was like, “Okay, if the house is going to burn down, I’m going to go…” Like the piece of this, that in some ways I can have control over is, “I’m going to actually burn the whole land down. The whole homestead.” The hard thing about that is, of course, some people stay there. They get lost there. They’re walking through the ashes forever. And luck… And I’m so grateful that that wasn’t my fate. That I had to do that stuff in order to realize that I wasn’t the person my father raised me to be. My father didn’t raise me. I was the person my mother raised me to be. And the best thing I could do, and this is why I said that so much of that stuff was about love is I realized I was trying to show the world, “Listen, this amazing woman is gone. And I am suffering.”

Cheryl Strayed:

I wanted to, with my own life, demonstrate how gigantic that loss was. And what I realized is the only way I could do that, the absolute only way I could do that, was to make good on my intentions. To make good on my ambitions. To be the woman my mother raised me to be, as I said in Wild. To become. To become. And she didn’t get to all the way, or as long as I hope she would, but that I would have to just simply live my life and try to honor her with it. And what’s so crazy and cool and beautiful about that is I did. I mean people all over the world know my mom’s name.

Debbie:

Yeah. They do. It’s interesting. You brought her to life through your words and she brought you to life through her life. It’s a really nice symmetry there.

Cheryl Strayed:

It’s crazy. You know I lost her… I was the same age when she died as she was when she was pregnant with me. So I lost her at the same age that I came into her life. I just want to say, I don’t want to in any way glorify the destructive things we do because they are destructive. And like I said, people get… Their lives… They’re lost there. And so in no way am I saying like, “Well, you have to do this to get to there.” I wish that I didn’t have to go into the darkness, but I was always trying to move in the direction of love. And as you said, I did write about her. And so not only is it cool, like I brought her to life, but I also got what I needed, which was… Remember when I said back then that in some ways it was a signal, like “Help me. I’m in pain, I’m suffering.”

Cheryl Strayed:

I felt so alone in my grief. And then when I wrote about it and told the truth about it, how savage it was, I felt like, “Okay, everyone’s going to think I’m crazy.” But instead what everyone thought was, “Me too.” To this day, really now hundreds of people, hundreds of thousands of people around the world, maybe millions of people around the world are saying, “I know how you feel because I felt that way too.” And I’m suddenly not alone in my grief. And I’m always shocked by that.

Cheryl Strayed:

Every Mother’s Day or very often on Mother’s Day, I’ll make a post on Instagram or something about mother loss and I’ve gotten to the point where it’s not so much for me anymore. It’s not like me saying, “Oh, I miss my mom.” I do miss my mom, but I’m doing it because I know that other people need me. They need to hear the story of that loss so that they’re less alone in it. And so in so many ways, I can’t get my mom back through my writing, but I can get love through my writing. And I can get love specifically in that place of loss, if that makes sense.

Debbie:

Absolutely. Absolutely. I mean, I am very grateful looking back on my life, and maybe this is synthesized happiness I’m not entirely sure, in terms of what it has given me in terms of my ambition or my creativity or even just my sense of the world. But I also deeply, deeply regret the pain that I caused others with my own self-destructiveness. And one of the biggest regrets that I have, what I put other people through in that journey to be who I am and where I am now. But I also know that I couldn’t have survived in many ways without that destructiveness and that testing of who I was as I revised myself, so to speak.

Cheryl Strayed:

Yeah.

Debbie:

Do you think that part of that revision for you was to change your name?

Cheryl Strayed:

Oh, absolutely. Mm-hmm (affirmative). Yeah. So I was born Cheryl Nyland, as you said, and then I got married young. I was Cheryl Nyland-Littig. We both hyphenated our names and because we were trying to be radical and feminist and cool. Which it was a weird thing to do back then in those years.

Debbie:

It’s interesting. I have my dearest, dearest cousin who’s practically my sister did that too. And her daughter has the hyphenated name and says that that’s the worst thing that they ever could have done to her, giving her two long names that don’t even fit on a student ID card.

Cheryl Strayed:

It’s just… Well, and then nobody remembers both names. They’ll just decide to call you. And people will just be like, “Okay, whatever, I can’t figure out your name.” And so when I got divorced right before I went to hike on the Pacific Crest Trail in 1995, I was getting divorced in like 94, 95, I realized that… Yeah, so I had to set my life on a new course, which was really the old course, which was the course way back when I was like hiding Jane Eyre in 10th grade or whatever, thinking of those plans for myself. I took a little detour, did some other things. And then I was like, “Okay, this is life. My mother’s dead. My first marriage is over. This man I loved, but got married too young. And I’m an orphan. And I need to make my life. I’m going to make my life.” And part of that, obviously for a writer, is about language and Cheryl Nyland just didn’t feel like me.

Cheryl Strayed:

And so I came up with my own last name, Cheryl Strayed. What’s so funny to me now… So I’ve been Cheryl strayed longer than I was anything else. Now I’m 51. People still say like, “Oh, but Cheryl Strayed’s not your real name.” And I’m like, “Yes, it is.” And it’s funny to be like if I had married a dude named Joe Strayed, nobody would say, “Well, Cheryl Strayed is not your real name.” It’s real if it’s tethered to a man that you’re tethered to, but it’s not real if it’s tethered to your own vision of who you are. And a lot of people, they don’t even have ill intent when they say it’s not your real name, it’s just their… our way of thinking.

Debbie:

It’s just how we’re socialized. I know. It’s horrible.

Cheryl Strayed:

And so what I hope to do is to try to-

PART 2 OF 4 ENDS [00:46:04]

Debbie:

I know. It’s horrible.

Cheryl Strayed:

And so what I hope to do is to try to get people to think differently about it. Cheryl Strayed is the realest name I ever had.

Debbie:

So you talked about your hike along the Pacific Crest Trail. You were 26 when you embarked on this solo three month, 1,100 mile hike. If you knew that there were people listening who are considering taking this same hike, what would you share with them? What would you tell them? What advice might you give them?

Cheryl Strayed:

Well, absolutely go. If you have any… Whether it’s the same hike as mine or any long hike, if you have any desire to do this, do it. Okay? I’ve talked to so many people who have taken long walks and long hikes and all of them say, “Oh, that’s the best thing I ever did for myself.” Because walking, especially walking a long way, for many days on end, day after day, it’s a deeply, deeply challenging thing. So you gain your sense of your own strength and your own ability to endure difficulty, monotony, pain. And of course, what happens on the outside, one foot in front of the other, in front of the other, also happens on the inside. It turns out for me the way to heal anything is to keep going and to keep going with humility and faith and a sense of optimism, even when it looks and feels really hard.

Cheryl Strayed:

And I love this idea of the body teaching us what the soul and the spirit and the heart needs to know. And that’s what happens on a long walk. That’s exactly what happens on a long walk. I mean, I can’t say enough what a powerfully humbling and healing act that was.

Debbie:

As I was rereading the book and watching the movie again, I thought that it was very likely the last moment, or almost the last moment, that we weren’t all walking around, checking our email, and texting on our cell phones.

Cheryl Strayed:

Yeah.

Debbie:

And it seems unimaginable to me to consider hiking 1,100 miles in near solitude with the phone off the entire time. I mean, it’s just not even comprehensible. What would people say?

Cheryl Strayed:

Well, and that’s… This was 1995.

Debbie:

Right.

Cheryl Strayed:

I didn’t realize until… I was sort of midway through Wild that I realized, “Oh, I’m actually writing a kind of historical memoir about a world that is no longer, a world that is now past.” That our experience of the wilderness is now one where, first of all, we can just research everything online. You know, where does that trail begin and end? Where’s the water, where’s the…” I had-

Debbie:

Google Maps, right?

Cheryl Strayed:

And that was one of the things. And of course, in Wild, I did make [inaudible 00:48:57] of like unpreparedness or whatever. But the other piece of this, I want to say, is that I prepared to the extent that I could, that there wasn’t the internet. I went to the Minneapolis Public Library and said, “What books do you have on the Pacific Crest Trail?”

Cheryl Strayed:

And they had one and it was the book I already purchased at REI. It wasn’t like things were available, you know? You just had to go and see how it was. Yeah, I was absolutely alone. The first eight days of my hike, I didn’t even see another person. What I learned is that that would be a regular thing, that I would many, many times go three, four, five days without seeing another person. There was no way to contact anyone, except if I came upon a payphone or if I sent them a letter.

Debbie:

Right.

Cheryl Strayed:

I’m so grateful for that world. I mean, I’m so grateful that I took my hike during that time because I think had I not done that I would have spent a lot of time tweeting at people and-

Debbie:

Instagram, right?

Cheryl Strayed:

[crosstalk 00:49:58] Connecting with people.

Debbie:

With all the great pictures, the fox. I mean…

Cheryl Strayed:

Yeah. And getting feedback from people and not just sitting in my solitude. I mean, that’s the thing about that kind of deep solitude is it’s just you and there’s nothing to do, but reckon with yourself. There’s nothing to do, but have that conversation with yourself in your head. There’s nothing to do, but allow those memories to emerge. By the time I was finished with my hike, I honestly felt like I had thought about everything I remembered in my whole life, every relationship, every person. What a therapeutic experience.

Debbie:

Monster was the name of your backpack, which at its heaviest weighed nearly 70 pounds. Even at its lightest, it was 50 pounds. And making yourself suffer in a physical way kind of feels like the opposite of fun. And I read that you said that the act of remembering your suffering can become pleasure afterwards. And I wanted to know like, how so? How does that become pleasure?

Cheryl Strayed:

I’m such a believer… I call it retrospective fun. Okay? And this is the advice, too, I’d give someone wanting to take a long hike… Is you just have to… Or really any kind of journey. You just have to acknowledge that very often the best things we do are painful and complicated and difficult and exhausting and require us to be out of our comfort zone and to accept difficult things, right? If the journeys we take are just like exactly how we imagine they’d be and planned they’d be, and everything was idyllic and blissful, and there was no sort of difficulty, we would be like, “Yeah, that was fun.” But there’s nothing about it, right? There’s no texture to it-

Debbie:

Yeah, no grit.

Cheryl Strayed:

No grit. And I think that the grittier an experience is, the more it teaches us. We never, ever, ever forget the lessons we learned the hard way. I began a backpacking novice. I became a backpacking expert. I thought that I couldn’t do that and I did. I over and over and over again said to myself, “I can’t go on. I can’t.” And I always did. And then that becomes part of who you are. It becomes part of the story you tell yourself. So then, 10 years later, you’re in labor, as I was trying to give birth to my 11 pound baby boy, and I was thinking, “I can’t do this.” And what the deepest voice in me said, “You know you can. You know you can.”

Cheryl Strayed:

So I think that that’s the piece of seeking out things that aren’t necessarily the most fun in the moment, but will be the fun things in retrospect. And the funny things too. Like one of my theories about travel is that none of us wants to get like terrible diarrhea in Guatemala, but if you do… Or Cambodia or wherever, but if you do, they will be the funniest stories you have about your travels, you know?

Debbie:

Absolutely. Absolutely.

Cheryl Strayed:

So it’s like just embrace the hard times, you know? I think that that’s really what we’re seeking is to get to see ourselves in all kinds of lights and travel offers us that.

Debbie:

Nine days after your hike, and a few days after your 27th birthday, you met your husband through someone who came to the yard sale you had selling your hiking gear to raise a little bit of money to live on. Several years later, you married him, you had two children. Do you think that this sort of “new life”, big quotes, was the gift you got at the end of a long struggle? Do you think it was just luck? Tell me about how you view that sort of moment in time where you come back and everything changes.

Cheryl Strayed:

Well, I think it’s a combination of things, right? Like luck is always a factor in everything. How do we ever know that we’re going to be standing there when that person walks up and you say, “hello,” and then something is born of that, right? I think of Brian’s life and my life and thinking about how did our paths ever get to cross? How did your path cross with Roxanne’s? It’s a beautiful thing.

Debbie:

I went after her. I chased her. I did. I chased her.

Cheryl Strayed:

Right, but further back than that, Debbie, like beyond even… That you could even… I mean, it’s just fascinating, right?

Debbie:

Yeah.

Cheryl Strayed:

Of all the directions your life could have gone and hers, you know?

Debbie:

True. Yes.

Cheryl Strayed:

I just think it’s a cool thing to think about. So some of that is just luck. And of course a lot of it is that by the time I met Brian, I was okay. I was in a place that I was able to see more clearly again and be more kind to myself and to be truer to my nature and truer to my ambition and my vision. I was doing again, what I’m here to do. And when you’re doing that, and then you meet somebody else who’s doing that, it’s like really good timing, you know?

Cheryl Strayed:

So in so many ways it is a gift. Getting Brian is the gift of doing all of that wandering and searching and finding. And it’s not the end of the story of course. It wasn’t like, “Well now I’m just like all great and everything.” And then 25 years later, here we are in the same place. I mean, we’ve both struggled and grown and gone through all kinds of things, right? But to make yourself ready for that kind of relationship, I wasn’t walking the trail to do that, but that was one of the outcomes of it. Yeah.

Debbie:

You moved to Portland, you got a job waiting tables, you started working full time writing your first novel, Torch. And you then went to graduate school, to Syracuse University and got a Master of Fine Arts in Fiction Writing, so you could actually finish the book. What made you decide to do that? What made you feel like that would help you get to that moment where the book would be finished?

Cheryl Strayed:

Yeah, it was mostly financial and some also just like the logistics of giving myself real time to write. So all through my twenties, I was a waitress. I was a youth advocate. I was a vegetable picker on a organic farm. I was an EMT. I did all kinds of things, but what I was really doing was writing, that was my real work. And I had this big student loan to pay off. It was exhausting, always, to be just living hand to mouth and struggling financially while trying to write. And I sort of always thought like, “Okay, my first novel will of course be published and done and everything by the time I’m 30.” I think sometimes of that scene in Cinderella where the mice come and make her that dress. Do you know that scene I’m talking about?

Debbie:

Yes, yes.

Cheryl Strayed:

They scurry about and they grab like the curtains and the sash and they magically make her a dress. I was kind of hoping that that’s how my novel would be made, that I would one day just walk up to my lap… Not my… I didn’t have a laptop. I would appear at my computer and there would be the novel. That the mice-

Debbie:

[crosstalk 00:57:08] Yeah. That’s sort of how I thought my life would be.

Cheryl Strayed:

Wouldn’t that be so nice?

Debbie:

Yeah.

Cheryl Strayed:

So I just said, “Okay.” As I was approaching 30, I was like, “Okay, this hasn’t been done yet and here are the reasons why.” One is, I’m always having to work full time to pay the bills. And two, you know, it’s hard to have that kind of time and focus when you’re working full time. So graduate school kind of solved that problem for me. And I only applied to graduate schools with the idea that I would only go if I were offered a full fellowship or scholarship and tuition remission and that it wouldn’t put me further in student loan debt. And so I applied to a bunch of those programs and was accepted into all of them. And I chose Syracuse and off to Syracuse I went. And it was really there that I was able to write that first book. I wasn’t finished with it by the end of graduate school, but I was close enough that then I just stuck with it and finished it within about a year after I finished grad school.

Debbie:

You wrote this about the experience of writing Torch. “If my kids read my journals when I die, what they’re going to find is that if they didn’t know that Torch had been published, they would think that I had failed to write my novel because the whole journal is me lamenting about how I can’t write and what a failure I am and all of this negative stuff about how I can’t do it, and I’m not doing it, and I tried to do it, but it sucks. That’s the narrative. Then meanwhile, what I was doing was writing my book. So when the same thing happened with Wild, I was like, ‘Oh, this is how it feels to write a book. I’m writing a book because I feel like a failure.'” Cheryl, do you still feel that way when you write?

Cheryl Strayed:

Yeah. So much. I mean, so much to the extent that even just you reading that to me, I was like, “Oh my gosh, I needed to hear that.” Because I feel that right now. I’m like, “I can’t do this. I can’t do this.” Yeah. This sense of doom and doubt and like, “I can’t do this.” And all that freak out. But I beat up on myself a lot when it comes to this stuff. And then I just put one foot in front of the other and keep going and get the work done. And that is my process. For better or worse, I wish that I had this kind of sense of like, “Oh my gosh, another day where I get to be living the dream.”

Debbie:

Terror is just part of the process, right?

Cheryl Strayed:

Yeah. And sometimes within my writing, I’ll go into this great zone and I’m like, “Oh my gosh, why was I complaining? I love this. This is amazing and fun and what I love to do.” But I do have to kind of weed through a lot of doubt and fear to get there.

Debbie:

Torch was published in 2006. At that time you had two children under the age of two, 18 months apart. You started writing Wild in 2008, 13 years after you completed the hike. Initially you thought it would be a collection of essays, your second book, what changed?

Cheryl Strayed:

Yeah. Well, the reason I thought it would be a collection of essays is I thought, “There is no way in hell that I can write a book while having two little babies and being in financial stress, all of this.” I just thought I can’t write another book. And at that point I had started writing essays and had published essays in various places. And I saw that those essays together kind of told the story of my twenties and the missing story was my hike on the PCT. So I was like, “All I have to do is write the essay about my hike and I’ve got a book.” You know, because publishers are going to be so excited about publishing my collection of essays. But anyway, I thought I’d try. And what happened is I started writing and then it went on and on and on and on.

Cheryl Strayed:

And I was like, “Oh, I have a bigger story to tell.” And really, I didn’t know that until I was doing the writing because I found the bigger story when I was writing. And by the bigger story, I mean the story that exceeds the kind of like, “Oh, here’s my interesting journey,” or “Here’s the big loss I suffered.” You know? I knew that I needed to find a universal thread, that I needed to have… That my journey and my loss and my experience would have the potential to be expressed in a way that other people would see themselves in it. And it took some writing for me to figure out how to do that or to figure out that that was there.

Debbie:

You said that being a memoirist is about learning how to reenter previous versions of yourself.

Cheryl Strayed:

Yeah.

Debbie:

How do you go back into that previous version while still maintaining who you are?

Cheryl Strayed:

Well, you enter the magic of writing. That’s what’s so cool about it is… So what I mean by that is this. The only way for me to write about my real heartbreak over the decision to end my first marriage is to abandon the woman I am now who says, “Oh my gosh, I was too young to get married. And he was great and everything, but it’s a good thing we broke up because now we’re both married to other people and we’re happy.” You know? So leave that person at the door and start writing your way into the person who was in love with this man truly and who also felt like she could not stay with him, who had to break his heart and her own in order to live the life that she, for whatever inexplicable reason that was still kind of beyond her explanation, had to trust herself to do that.

Cheryl Strayed:

And so I went in and reinhabited that. And as I was writing, for example, that scene in Wild where my husband and I are deciding to get divorced, and then we get divorced and we’re saying goodbye to each other. I was just sobbing as I was writing it. And even though it’s actually not sad, like it’s actually not sad to me now. It’s a memory of sadness that I reinhabited. This was really made alive to me… I was on the set a lot when we were making the movie, so I was there like every day and really involved in everything. And there’s this scene, in the movie and in the book, where me and my ex husband, we’ve just mailed off our divorce papers and we’re standing on the street and we’re talking to each other and crying and embracing for the last time.

Cheryl Strayed:

And it’s very emotional. In the book, I’m crying. I’m like… It’s sad. And then I’m standing there with Reese Witherspoon right before she’s going to walk into the street with Thomas Sadoski, who plays my ex husband, and they’re going to begin shooting this scene. And she suddenly looks at me and Reese just starts sobbing. She was getting ready for that scene. And they go into the street and they shoot this and I’m standing next to the director. I’m watching this on the camera. And I noticed that some people on the crew were kind of gathered around me and a couple of them sort of put their hand on my back and put their hand on my shoulder to like comfort me.

Debbie:

Wow.

Cheryl Strayed:

And I thought, “Oh, okay.” It was so crystal clear to me because I was watching that scene and I wasn’t crying because it’s not sad anymore. But when I watched the scene of my mom dying, I cried.

Debbie:

Oh, that… How could-

Cheryl Strayed:

Because it’s still sad.

Debbie:

Yeah. I mean, it’s just… That’s beyond sad.

Cheryl Strayed:

And it doesn’t mean that one thing isn’t sad and one thing is. It means that there are different kinds of sorrow and some of them are sad in the moment and others are sad forever. And so I think that’s a really important thing that I try to remember still in my life, that it’s like, “Is this a sorrow that I’m going to carry with me forever? Or is it a sorrow that is like a crucible and I have to endure it and then I will be better for it.” That’s what I… When I wrote, as Sugar, “You’ve got to be brave enough to break your own heart” I was talking about exactly that thing where I had to make a decision that caused me and another person pain, but I’m better for it.

Cheryl Strayed:

And it’s not sad anymore. It was actually the golden key that opened the door to my liberation. And there was loss in that, but there was more gain. It became a gift in the end. And so, I think that for me, just as a writer, what you have to do is go back and be that person, that person before you got the golden key in your hand, or before you walked through that door, or before you made that next move. And just remember who that is and, through the writing, try to enter that consciousness again. And that does feel like magic to me, to go back and be like, “What was Cheryl thinking when she was 19 and decided to marry that guy? What was she thinking?”

Cheryl Strayed:

It seems foreign to me now. What was Cheryl thinking when she thought there was only one college to apply to and she had to stay in her state? It’s like, “Oh, well, that’s not the Cheryl I am anymore, but it is the Cheryl I was and she was informed by all of these things.” And to remember what they are is… It’s not only you got to do that to write memoir, but it’s a really cool thing to do for your life. Like very often I think how memoir writing is almost like the process of therapy, right? Where you go back there and you say, “Well, who was that person? And why did she do this and think this and love these people and leave these people?” And there’s always an answer if you’re willing to dig for it.

Debbie:

It’s so interesting to see how you change over time, without even knowing you’ve changed over time. And as I’ve gotten older, I’m going to be 59 year, and I can’t help but think, “I still feel like I’m 25. I still feel like I’m 35. I don’t understand how this happened.” And then I’ll go back and read journals from that time, 25 to 35, and I’m like, “Oh my God, I’m a completely different human being. It doesn’t even make sense that I’m the same person that that is.” Do you ever have that sense, going back to read the journals in remembering who you are or who you were?

Cheryl Strayed:

So I kept a journal all through… Basically from about 18 or 19 until shortly after I became a mother. And after I became a mother, I only wrote in my journal a couple of times. But so, basically from like 18 to 35 or 36, I have really a record, almost daily record of my life. And I want to just sit… And they’re paper journals that I wrote in. When I go back and read them, I think, “What? Like, who was I? What I was I thinking?”

Cheryl Strayed:

But I also, I guess more than anything, think, “Wow. I always knew.” I’m more amazed that I actually did have that sense of like direction or inner wisdom. I didn’t always have the ability to trust it, but I knew. Like I always knew who I was and what the right way was, even if I was confused and not brave enough to trust it or to take my own best advice. But it wasn’t like I was just like this completely different person and now I’m just like… I mean, in so many ways it’s like revisiting myself, you know? It’s not so much foreign. It’s more like a familiar visitation.

Debbie:

While you were working on Wild, you also started writing your column, Dear Sugar for The Rumpus. You were mentoring students at the Attic Institute in Portland, you were teaching workshops at universities, writing for magazines, but you and Brian, your husband, who’s a documentary filmmaker, were, as you put it, “epically broke.” You were, as they say, the classic starving artists.

Cheryl Strayed:

Yes.

Debbie:

And I also thought it was interesting that while you were writing Dear Sugar, you were giving people advice and in Wild you-

PART 3 OF 4 ENDS [01:09:04]

Debbie Millman:

Giving people advice and in Wild, you weren’t, but people have read it that way. I’m wondering how you feel about that, that whole notion of advice giving? I know you’ve referred to self-help work as intellectually mushy, and I think that too, but I do think that people look for that in work, even when it’s not there for their own needs.

Cheryl Strayed:

Yeah. When I was writing Wild, it never occurred to me that anyone would experience it as inspiring. I was really just trying to write the truest, rawest, realest story about that experience, about my grief, about my finding my way on this long walk, about the experience I had in the wilderness. Yeah, people do experience that in well, what’s the message of Wild? I’m like, ah, the message is whatever you think, whatever truths you find in yourself when you read it.

Cheryl Strayed:

But it even goes back to Torch, my novel. I realized after it was published that people were so experiencing this as a book that felt lifesaving. People felt consoled by it and said, oh my gosh, I can’t believe you wrote all that stuff about the stepfather because that’s what happened to me too. Or that’s what happened to my family too. People identifying with it.

Cheryl Strayed:

Of course, I guess that doesn’t really surprise me because that’s what I’ve taken from literature too. That’s what I meant when books are my religion is I felt saved by them, I felt seen by them. To me, I’m always sad, like in airports, many of these kind of little convenience stores in airports will have these little turnstiles that are… They’re inspirational or self-help. They’re never books. There’s never novels there. There’s never Tiny Beautiful Things there. It’s all these very specific things that are very instructive, like here’s your problem, here’s what you need to do.

Cheryl Strayed:

I find that the most helpful literature when it comes to what real self-help is things like, I don’t know, Jane Eyre, Alice Munro short stories. There I am in Alice Munro short stories. There I am in Toni Morrison’s Beloved. There I am in Mary Oliver’s poems. Those things-

Debbie Millman:

I guess that’s why people like Raymond Carver so much, too.

Cheryl Strayed:

That’s right. Raymond Carver. Named my son after Raymond Carver.

Debbie Millman:

I know.

Cheryl Strayed:

They’re my people. They’re my people in a Raymond Carver short story. So yeah, I didn’t intend for those things to be self-help, and frankly, even Sugar. When Tiny Beautiful Things came out it was in the self-help section of many books stores. I was like, what, what?

Cheryl Strayed:

I think of myself as an accidental self-help writer because of course Dear Sugar columns are self-help, and yet what they also are is literature. And to me, I’m not so interested in whether there’s a bright line between those two things or not, because in fact literature has been the thing that has been the most helpful to me when it comes to helping myself.

Debbie Millman:

It feels like you found your voice during your time writing Dear Sugar. Would you agree?

Cheryl Strayed:

Yeah. I mean, I think that… so Wild and Dear Sugar were written on top of each other. I became Sugar a week after I finished the first draft of Wild. Then I started writing Sugar, and then over that time that I was first writing Sugar, that first year, I was also doing the revision of Wild.

Cheryl Strayed:

I think that I was absolutely a real writer and a solid writer before that. But I think that to me, I wouldn’t so much say I found my voice during that time, but rather I found my authority, that my voice gained in authority.

Debbie Millman:

Oh, yeah.

Cheryl Strayed:

When I read Torch, which I haven’t read in ages, I read it and I’m like, okay, yeah. I can see that’s me. That’s me becoming a writer. That’s me being a writer. But in some ways it’s also me trying to really experiment with, well, who exactly am I? And do I have the confidence to be only that, to not also try to be like Mary Gaitskill or Alice Munro or Raymond Carver, to just be Cheryl Strayed.

Cheryl Strayed:

I feel like in Wild, I then was experienced enough as both a writer and a person where it is only me. Obviously, all my influences are always inside of me, but they weren’t in any way guideposts for me in any kind of technical way, the way they were in Torch. I just decided to trust my own life.

Cheryl Strayed:

And then with sugar, I stepped into it more because of course I had finished the first draft of Wild, so everything I learned in Wild was then brought into that, those Dear Sugar columns,

Debbie Millman:

Your next book, Tiny Beautiful Things, was published in 2012 and contains advice on love and life from your Dear Sugar columns. Nia Vardalos adapted the book for the stage and played the part of Dear Sugar in the sold-out 2016 production at the Public Theater in New York City, which I saw, which was just magnificent.

Cheryl Strayed:

Oh, thank you.

Debbie Millman:

I loved it so much. The play was directed by Thomas Kail, who co-created and directed Hamilton. He’s also been a guest on Design Matters, and somebody who I absolutely adore. How involved were you in the production?

Cheryl Strayed:

Yeah, I was really involved. From the very beginning, it was this thing that Tommy Kail and Nia Vardalos and also Marshall Heyman and I cooked up together. We met a few times around a table for a few days in New York and first of all, just talked about what it could be, what it might look like. Then Nia really went at the book and made it into a script, and we read it out loud to each other, and hashed that out, and talked it out, and then they started rehearsing.

Cheryl Strayed:

It was such a cool process to be part of because with adaptation, in both cases, with the movie and the play, I early on decided, okay, the book is mine. The book is what I made, and then now this is other artists essentially bringing their own lives and visions and thoughts to the work and making something new.

Cheryl Strayed:

I’m like the fairy godmother of it. I’m the great grandmother of it or something, so I wish it well, and I weigh in when I think it matters, but I also really just honor that relationship, I guess, that these other artists get to have their own relationship to the work and make something new of it. I was there every step along the way, but also just really bearing witness to that creation too.

Debbie Millman:

It’s now, when we get back to normal again, “normal” life, it is a play that’s going and traveling in regional theaters and so forth. Right?

Cheryl Strayed:

Yeah. It’s not traveling. What it’s doing is each different theater companies across the nation and in Canada as well, are making productions of it. It’s not one cast that’s going around from theater to theater. That each different theater licenses the play and makes it.

Cheryl Strayed:

Last year in 2019, it was one of the top 10 most produced plays in the nation. And we were looking… it was looking strong for 2020 too, and what happened is of course the pandemic, and then now we can’t gather. So that’s been really a bummer, but I hope that when we can gather again, that Tiny Beautiful things will be seen on many stages.

Debbie Millman:

Yes. I understand you’ve been at a crossroads now as different opportunities have come your way, weighing the reasons to do it, weighing the reasons not to do it. You’ve stated it’s not about the number of things on the list, it’s about the weight of those things. Almost always you think that the things that mean and matter the most really come down to one question, and that question is what do you really want to do? I wanted to see if you could help me understand how to know when something is the thing you really want to do?

Cheryl Strayed:

Gosh, again, with the hard questions. For me, that deepest wanting, it’s not that it’s the easiest thing to do. It’s the thing about which you feel like I can make, I can create something that feels larger than me if I decide to do this. If I write a book and not only is it a deep and true expression of some deep and true things I want to put into the world, if it’s not only that, and then it becomes also something that is meaningful to others, that’s a big thing to contribute to the world.

Cheryl Strayed:

I think that for me, that sense of rightness or a sense of if this mission is fulfilled, will it extend beyond my small little life? I feel that as a powerful call.

Debbie Millman:

One of the things that you are doing that I think is so, so helpful right now is hosting a new podcast.

Cheryl Strayed:

Yeah.

Debbie Millman:

From the New York Times, titled Sugar Calling. How would you describe it for our listeners?

Cheryl Strayed:

Sugar Calling was conceived when we all really that first week or so, when most of us in the United States were holing up and our states were going on shelter at home orders and so forth. A lot of people online were saying, Cheryl, we need advice. We need Dear Sugar to come back. And Lisa Tobin, who’s the executive producer at the New York Times in the audio department was like, how about bringing Sugar back? And I said, well, I don’t feel like my job right now is to give people advice about how to face this moment because I think so many of the questions would be so universal.

Cheryl Strayed:

Instead, how about we do it instead of giving advice that I go seek wisdom, and I seek wisdom from people, the source of so much wisdom. Books, as I said, have been the place where I found myself and found wisdom and insight. So how about I talk to authors, and specifically authors over the age of 60. That age group not only being wise elders, but also the group that we’ve been hearing over and over again are the most at risk of dying of this virus.

Cheryl Strayed:

I just decided to reach out to the literary elders who have informed me. George Saunders, who was my mentor at Syracuse University, Pico Iyer, Amy Tan, Joy Harjo.

Debbie Millman:

Judy Blume.

Cheryl Strayed:

Yeah, Judy Blume. It really is just a popup podcast. I did eight episodes, and then now I’m like, okay, I’m going to take a break and come back maybe. But it really was amazing to me how many listeners said, thank you. I needed that. I think it’s just a calming force to simply hear from people, yeah. You know what? Times have been hard before and I survived them. Times are hard now, we will survive this. And I love that that’s what the feeling that people get when they listen to the podcast.

Debbie Millman:

What is it like for you to be the person asking the questions instead of answering them?

Cheryl Strayed:

Oh, it’s so fun. I mean, it’s ridiculous. Seriously, I was like, what do you mean I get to call Judy Blume? Judy Blume. The way I described when I went to Harvard when I was 30 and I was like, this is such a far off land I didn’t even imagine it was real. That’s how Judy Blume is. It’s okay, wait, she’s an actual person. Okay.

Debbie Millman:

Right.

Cheryl Strayed:

Because for so long, I mean, that woman taught me everything. She taught me what an erection was. She taught me everything. She taught me so much.

Debbie Millman:

You are calling writers, all of whom are over 60, and you’ve declared that there’s something that’s built into our language wherein we associate old as an insult. Why do you think that is?

Cheryl Strayed:

Because we are such an agist culture. It was really interesting when I was trying to come up with the descriptive language for this podcast, and even asking the first guests, oh, are they going to be offended if I say, oh, writers over 60 because it’s like, oh… or am I in some ways putting them into a category that people don’t want to be in that category. It was just fascinating to me how we do see… if somebody calls me an old woman very often that feels a little bit like a slight insult, doesn’t it?

Debbie Millman:

Yeah. Absolutely. Yeah.

Cheryl Strayed:

At the same time that I was thinking about this, how to talk about the fact that I’m talking to elders, I was looking again at this book of poetry that my mother gave me a long time ago right before she died actually by the Japanese poet, Shintaro Tanikawa, and I’m probably saying it wrong, but that’s how it’s said phonetically.

Cheryl Strayed:

I was reading some of his poetry and it’s an English translation from the Japanese, and there are times where the English refers to old man and old woman. There’s a translator’s note, and it says that there’s not a word in English for the exact word in Japanese. In Japanese, old man and old woman that word is actually a very respectful word. It’s actually a very reverent word, and then when it’s translated to English, it sounds like an insult. Like old man, old woman. Hey, old man. Hey, old woman. And I was like, oh, that’s the problem. It’s a language problem.

Cheryl Strayed:

But language of course follows culture, and so it’s just like the word fat. People are all confused about the word fat now because people are reclaiming that word and saying, look, you’ve decided that fat is a negative word. I’m going to say I’m fat.

Cheryl Strayed:

When we did this on the Dear Sugar’s podcast, we had Lindy West on and we got letters. People were like, why were you referring to her as fat? That’s so insulting. It’s was like, no, no. She’s saying she’s fat, and she’s not insulted. It’s complicated.

Cheryl Strayed:

I mean I do think that it made me really awake to the fact that we do not… I mean I knew this before, but wow. We do not treasure and value our elders. We consider age something that we should avoid mentioning. And I think, yeah. There is wisdom in age. People who are over the age of 60 have been around longer than many other people, and they have something interesting to tell us. Judy Blume is 82. She has a whole lot of time to look back on and reflect on. She has so much to offer us because of that experience.

Debbie Millman:

Oh, yeah. She’s a national treasure at this point.

Cheryl Strayed:

She is. But why have we construed that to be, oh, people who are older are not with the times or they’re out of step or they’re even kind of stupid, right? That they don’t have the kind of clarity or quickness that young people do, and that’s just a bad story we’ve told ourselves, I think.

Debbie Millman:

Well, thank you for helping to change that.

Cheryl Strayed:

It’s been so cool to be like, no, I’m talking to the old people and it’s not an insult. It’s a beautiful, joyous thing.

Debbie Millman:

Cheryl, I have two last questions for you.

Cheryl Strayed:

Okay.

Debbie Millman:

The first is something that I was really heartened to read about. I understand that sandwiches are problematic for you.

Cheryl Strayed:

Of course, they are. Sandwiches are just like chaos machines, right?

Debbie Millman:

Absolutely.

Cheryl Strayed:

They’re just like willy nilly. See, I know you’re my sister. I know you also feel this way, that things have to be orderly.

Debbie Millman:

Absolutely. Every bite has to be perfect.

Cheryl Strayed:

Not only do they have to be orderly… Yes, the whole goal of a sandwich for me is to make every bite as much like the previous bite as possible.

Debbie Millman:

Yep. Uniform.

Cheryl Strayed:

Okay. Consistency. You put the… whatever you’re putting on it, it has to be uniformly applied everywhere.

Debbie Millman:

Absolutely.

Cheryl Strayed:

Burritos also sometimes have this problem. If people don’t do the burrito correctly, yeah. It’s just a mess.

Debbie Millman:

Tacos. Absolutely.

Cheryl Strayed:

Yeah.

Debbie Millman:

Yeah. This is my last question. Cheryl, what is the thing you want to do most next?

Cheryl Strayed:

Finish my next book. I really am ready to do that. Wild and Tiny Beautiful Things were published within four months of each other in 2012. And basically my life was just an absolute… it was just like a volcano.

Debbie Millman:

Yeah, movies and Oscars.

Cheryl Strayed:

The movie and the play, and I was and I was involved in the podcast and the public speaking career. Also, the kids. During all this time, I have these two little kids.

Debbie Millman:

You’re a mom.

Cheryl Strayed:

Who now are 14 and 16, and I just feel like, wow, okay. I really now am ready to go back, go back to that basic, go back to that sit there and write your next book. And so that’s what I’m doing and I really want to do it. And I’m really excited about it. I’m also afraid and doubtful and scared. I’m all the things I am when I’m writing, which means I’m writing my next book.

Debbie Millman:

I can’t wait to read it. Cannot wait to read it.

Cheryl Strayed:

Thank you.

Debbie Millman:

Cheryl Strayed, thank you so much for joining me today on Design Matters with such an open heart and so many wonderful things to say.

Cheryl Strayed:

Thank you. Debbie, you are a woman after my own heart, I swear. We have to meet in real life someday and have sandwiches. Okay?

Debbie Millman:

Absolutely. I would love that. I would love that.

Cheryl Strayed:

Thank you, my dear.

Debbie Millman:

Oh, my pleasure. You can find out more about Cheryl Strayed on her website@cherylstrayed.com. You can hear her podcast, Sugar Calling, on all of the podcast networks.

Debbie Millman:

This is the 16th year we’ve been broadcasting Design Matters, and I’d like to thank you for listening. And remember, we can talk about making a difference, we could make a difference, or we can do both. I’m Debbie Millman and I look forward to talking with you again soon.

Speaker 3:

Design Matters is produced by Curtis Fox Productions. In non pandemic times, the show is recorded at the School of Visual Arts Masters in Branding Program in New York City, the first and longest running branding program in the world. The editor in chief of Design Matters is Zachary Petit, and the art director is Emily Weiland.