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Did you know that Ted has 17 podcasts with more to come? This is an episode of The Design Matters with Debbie Milman podcast. On this episode, a conversation with writer Cheryl Strayed about her childhood, her career, and on the value of taking a very long hike. If you like what you hear, subscribe to design matters wherever you're listening to this.
This is Design Matters with 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 Kael. 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. I'm joined by Cheryl Strayed, who is recording herself in her home in Portland, Oregon. Cheryl Strayed, welcome to Design Matters.
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.
Oh, I'm so glad. I'm so excited. I listened to a recent podcast where you said that this pandemic has made it clear to you that the first thing you are as a writer was that ever really in doubt?
No, no, it was never in doubt inside myself. But what I meant by that is one of the things that happened after a while 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 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, you know, traveling the world, giving talks.
And I and I am like I actually have a whole career of that in addition to my writing. And that was born out of a combination of, you know, wild success. And then also my you know, much to my surprise, I'm good at it and I enjoy it.
I understand that you're a 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.
It's really interesting, isn't it? I mean, for me, I 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 like if I'm in a place, whether it be emotionally or professionally or financially, that that that it's not a good place, I think, OK, 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 detail person. I love maybe that sense of control that I have when I look at my calendar, I go, OK, we're going to do this in June and that's in July and that in August and this time next year will be here. You know, 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've met we met in 1995, so I guess it'll be 25 years since we met this fall. The September, my running joke with him, you know, we've been fighting for 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 like he'll put something on the calendar.
And I'm like, that is the sexiest thing you ever did for me. Yeah. Yeah. I totally lost my love language.
Yeah. What about you? Well, I. I know that you're a list maker and you're not only a list maker, but you make sublist hear lists.
And I do the same thing 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 two year calendar and I am attached to this thing.
It goes with me everywhere.
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, you know, that was the first thing like, OK, everything is canceled in March and April and maybe May, but June and July and August are totally on. Right. And then as the weeks passed and I realized, oh, my gosh, you know, and I finally, you know, I had to do.
The thing I have many times advise 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. Right. Because then you can work from a place of reality rather than delusion. And so I'm trying to accept it and let go of.
The future, or at least my sense of knowing what's going to happen in the future, 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 Niland in Spangler, Pennsylvania. Yeah. 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.
Mm hmm. Did you realize that at the time? Gosh, that's such a great question.
I did 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 and in so many ways communicated to me and my 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 of wonder and love and light and the beautiful things. But we were living in a house that was, you know, 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, you know, we witnessed I witnessed my brother and sister and I all witnessed horrifying things, things that I that I never witnessed beyond that, you know, as an adult. I mean, I was always a little child. My first some of the first things I saw were really, you know, my mother being beat, beaten by my father, my mother almost being killed before my eyes and my father, my mother being raped by my father.
And so my memory, my perception of what I understood in those years. It's definitely one of fear and 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 but also a lot of light and joy and fun and no longer being under the the sort of weight of that fear that you have when you live with somebody who's abusive.
I, I completely understand in many ways.
I had a lot of similar experiences so that a lot of the questions I'm going to ask you are really not only from 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.
You know, this is happiness. Mm hmm. 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. Well, that's so resonated with me. What do you think you had to teach yourself?
Like, what is the biggest thing you think you had to teach yourself?
Oh, you don't ask little questions. Do you know? You asked big questions. Big questions, sorry. Big questions.
You know, I think that the biggest thing is that I'm OK in this world. I have the strength and the courage and the resilience and the heart to be OK, 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 I wrote about this in a while, too. But so right after my mom died, I was living in Minneapolis. I was twenty two and a friend of mine gave me a gift certificate to see an astrologer. And I was like, OK, well, I don't know, like what says astrology stuff, you know?
And but I thought, OK, I'll go. And I went and I talked to this woman, Pat Kaluza, and she had this like hippie sort of place in Minneapolis, and she read my birth chart. And it was astounding and amazing. 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 is troubled or he's you know, and I kept saying, like, oh, yeah, my father is 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 and who hasn't healed his or her wounds, you you as the child, you're wounded in the same place.
And so you're going to have to heal that wounds.
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. And, you know, I would say that that extends beyond necessarily the father. I think that, you know, 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 but the most the biggest one you ask what the most important one I think it was that sense is that. 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 like always brave or always do the right thing or always accept what's happening in a sort of 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.
I think that as I was rereading Wilde and as I watched the movie again, too, which was really wonderful.
I also got the sense that that your journey was one of finding out if you could rely on yourself, if you could take care of yourself, pretty extreme way.
Yeah. Testing yourself. But but I got the sense that that ability to do that was was also underneath everything else that you were doing.
I think so, too. And, you know, I think I want to say to like I think though we all need to do that. You know, obviously somebody like me who had a father who was abusive and not, you know, not the father that any one wants. And then and then a mother who died, I was really an orphan. And, you know, I had to go and find those things, as you say.
And yet I think part of maybe the human journey is that like 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 and also finding their path, you know, 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. And and that's why, you know, 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 had given myself my own rite of passage. And I said, like, you have to go test yourself to see who you are.
And that's those rituals of rites of passage are what what we've done as humans throughout all time, across every culture and, you know, continents 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.
When I was doing my research on your childhood and adolescence, they came across a couple of little facts that really were wonderfully surprising. I know that when you were 13, you moved to Aitkin County. It was very narrowly 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 this, Cheryl Strayed, you were a high school cheerleader and the homecoming queen.
And so you you were an overachiever from day one. Aha. I was. I was. So let me explain. My stepfather, who was a carpenter, he was seven years younger than my mom.
They they married when I was like 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 the like the small town attorney in Chaska, Minnesota. And he said, you know, 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. So by the end of the year, they got a twelve thousand dollar check. That was the payment for a broken back back in nineteen eighty or so. And my mom said, you know, 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, 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.
So, yeah, my my rebellion in my teen years was to seem to be a version of myself that thought that I wanted to project a sense of success and grace and togetherness. And I you know, I wanted to be popular because to be popular is to be loved. I wanted people to love me.
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 novel Johnny Got His Gun is a book that first exposed you to the power of inhabiting the life of another human.
Yeah. What was that like for you? How did how did that infuse who you were?
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 know, you're inside the mind of a man who's had, you know, been deeply injured in the war and lost his limbs.
And he's, you know, you're just living in his head and and having his memories and his delusions and his his sorrows and his rages. And you're right there inside of him.
And I think it was this maybe the first book that the material was so utterly dark and painful and true that it was the it was the first time that I understood what war was, what grief was.
You know, 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.
And and, you know, I loved books long before that, 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 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 like what did they really feel?
What do they really think?
What was their actual experience of being human?
And so in Dalton Trumbo book, I was like, wow, I've finally been let in to that to that secret.
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 it on the top of a soft serve ice cream cone like a pro.
Of course I work 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 our abilities, you know, I wanted things like brand name shoes or Levi jeans, like we would go to Kmart and at the beginning the school year, and we'd each get like 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, you know? And my mom would say, I can't afford it. So as soon as I could, you know, I babysat before that. But but honestly, as soon as I could, I got myself a job and I was like thirteen and a half. I sort of fudged my age. I think you had to be 14 to actually work.
But by 13, I worked as a full time job as a janitor's assistant and in my school, cleaning the books that the shelves and the drawers and the desk getting gum off of things and painting. It was through this program for low income kids. You know, I worked and I earned my money and I bought my stuff. That's that was part of the whole plan, you know, that I would get it myself if it couldn't be provided for me.
Sometimes I talk to my peers who were like going to camp or going to Paris or whatever, and I envy them. 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. And I did that all summer and they were minimum wage jobs. But but they were the first lesson I had and really how to be self-sufficient and making it happen, like not expecting others to make it happen for you.
And I treasure that. Like, I think I learned more doing that than I would have going to a lovely summer camp. But, you know, we all learned we all find our way.
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?
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 a very. Our way 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, did my best, and I went to I put in my application to one school and and I applied to this one school because it was a small school. I was overwhelmed of thinking, like going to like the University of Minnesota. It just seemed too big.
So, yeah, you know, I look back at 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.
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 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 quit. I took a class really in that first year or so with Michael Dennis Browne, the poet Michael Dennis Browne and my eyes, I just everything, oh, you know, absolutely exploded.
And I thought. I have to trust this, I have to you know, I thought that I could sort of funnel my my desire to write into the channel of journalism because it's the job, you know, that you can actually get paid to write.
But I don't want to do that. Like, I want to really put all of my heart and my faith in and 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 that I was absolutely relentlessly, ruthlessly committed to following through and being, you know, just really, really, you know, holding hard onto that thread.
That was my writing and doing it and doing it and doing it until I succeeded. And you know, it's funny, as I say, these words, you know, the 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 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 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, you know, publish a story like I would never, ever, ever be talking to you right now.
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.
Yeah, well, and of course. And of course, when did I say I'm not afraid? And I was. Yeah.
And, you know, even to this day, like, writing is so hard for me. It's so hard for me. 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, you know, go all the way to the finish line.
In March of 1991, when your mom was 45, you were 22, your mom died of cancer, and you 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.
Mm hmm. And I wanted to ask you about that destructive thing that we do. Why do you think we hurt ourselves when we're hurt?
Mm. Well, again, you you with the big questions, Debbie. I kind of want to say I'm sorry, but I'm sorry. It's so it's 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. Yeah, 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. And in so many ways, that's, you know, when you turn to drugs, for example, you know, that's a way of of pushing others away from you. Right. 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? I also think in my case, there was this sort of division within me or this polarity that was the that's almost like it's almost like mythic in its you know, when I think about it and I interpret it this way, is like the mother, the good mother who's been taken from me and the and the bad father.
The dark father who abandoned me.
You know, if I can't be the the woman my mother raised me to be that ambitious, generous life, you know, 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 he'll. And understand and revise, and I think that a lot of us have to do that, you know, I think that a lot of people who are suffering and certainly people who have written to me as sugar, you know, they have a problem.
They write with the problem right there. Like, this is my question. This is my thing. But really, the problem is, is that deep, deep river that's flowing beneath all the troubles that that subterranean channel, that 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 you have to heal them.
And sometimes, you know, healing is an ugly thing. Sometimes healing is destruction. Sometimes healing is turning away. Sometimes healing is a kind of rage and anger, you know? 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 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, OK, if if the house is going to burn down, I'm going to go like the the piece of this that I in some ways I can have control over is I'm going to actually burn the whole the whole, you know, the whole land, like 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, you know, that that I had to do that stuff in order to realize that.
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, as I realized, like I was trying to show the world, listen, this amazing woman is gone and I am suffering. I wanted to, you know, with my own life, demonstrate how how 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, and wild to become, to become.
It's interesting you brought her to life through your words and, you know, she brought you to life through her life. It's a really nice symmetry there.
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 that I came into her life. Right. You know, I wish that I wish that I didn't have to go into the darkness. But, you know, I was always trying to move in the direction of love. And 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, OK, everyone's going to think I'm crazy.
But instead, what everyone thought was me, too, to this day, you know, to this day, really now, you know, 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 and I'm suddenly not alone in my grief. Yeah. And I'm always shocked by that. 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.
You know what 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 of who I was as I revise for myself, so to speak.
Yeah. Do you think that part of that revision for you was to change your name? Oh, absolutely.
Mhm. Yeah. So I was born Cheryl Milind as you said, and then I got married young. I was Cheryl Milind Littig. We, we both hyphenated our names and because we were trying to be radical feminist and cool, which it was a weird thing to do about that. And so yeah when I got divorced right before I went to hike on the Pacific Crest Trail in 1995, I was getting divorced 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, you know, way back, you know, when I was like hiding Jane Eyre in 10th grade or whatever. I think now those plans for myself, I took a little detour, did some other things, and then I was like, OK, this is, you know, 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 Niland just didn't feel like me. 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 is not your real name.
And I'm like, Cheryl Strayed is the realest name I ever had.
So you talked about your hike along the Pacific Crest Trail. You were 26 when you embarked on this solo three month, eleven hundred mile hike.
If you knew that there were people listening who are considering taking the same hike, what would you share with them? What would you tell them? What advice might you give them?
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 because it is walking, especially walking a long way for many days on end day after day.
It's it's it's a deeply, deeply challenging thing. So you get you 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 that, you know, it turns out for me, you know, 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 and, you know, I just I love this idea of the body teaching us what 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.
And it seems unimaginable to me to consider hiking 11 hundred miles in near solitude without a phone on the Internet. Well, the phone off the entire time, I mean, it's just not even comprehensible. What would people say?
Well, that's really this was nineteen ninety five. And I didn't realize until, you know, 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 that, that 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 is the water? Where's the you know, I had this right. You know, and that was one of one of the things and of course, and wild, I did make comic 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. You know, I went to the Minneapolis Public Library and said, you know, what books do you have on the Pacific Crest Trail? And they had one. And it was the book I already purchased at RTI. It wasn't it wasn't like things were available. You know, you just had to go and see how it was.
Yeah, I was absolutely alone. I was the first eight days of my hike.
I didn't even see another person.
What I learned is that that would be, you know, a regular thing like that. I would many, many times go three, four or five days without another seeing another person.
There was no way to contact anyone except if I came upon a pay phone or if I sent them a letter. Right. 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 in town. Right. Connecting great pictures to Fox. I mean.
Yeah. And getting feedback from people. Right. And not just sitting in my solitude. I mean, that's the thing about that.
That kind of deep solitude is it's just like it's just you and there's nothing to do but reckon with yourself. There's nothing to do but to have that conversation with yourself in your head. There's nothing to do but allow those of 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.
Monster was the name of your backpack, which at its heaviest weighed nearly 70 pounds, even if even at its lightest it was fifty 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?
I'm such a believer. I call it retrospective fun. OK, and this is the advice to I'd give someone wanted to take a long hike, as you just have to, or really any kind of journey.
You just have to acknowledge that, 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 imagined they'd be and plan they'd be and and everything was idyllic and blissful. And there was no there was no sort of difficulty.
We would be like, yeah, that that was that was fun. But, you know, there's there's nothing about it. Right. There's no texture to it. Yeah. No, no. Great. And I think that the the grittier an experience is, the more it teaches us, we never, ever, ever forget the lessons we learned the hard way. I began the 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, you know, ten years later, you're in labor. As I was trying to give birth to my eleven pound baby boy and I was thinking, I can't do this. And I what what the deepest voice in me said, you know, you can you know, you can.
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?
Well, you know, I think it's it's a combination of things, right? Like luck is always luck is always a factor in everything.
You know, how 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 that's born of that right now, I think of Brian's life in my life and thinking about how how did our paths ever get to cross? And and of course, a lot of it is that by the time I met. Brian, I was OK. You know, 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. So in so many ways, it is the gift. You know, getting, Brian, is the gift of. Doing all of that laundry and searching and finding and it's not the end of the story, of course, it's like it wasn't like, well, now I'm just like all great and everything. And and then, you know, 25 years later, we're just here we are in the same place.
I mean, we've both struggled and grown and gone through all kinds of things. Right. But, you know, 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.
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 that were where the book would be finished?
Yeah, it was it was mostly financial. And some also just like the logistics of of giving myself real time to write. So all through my 20s, I was a waitress, I was a youth advocate. I was a vegetable picker in an organic farm. I like I was an EMT. I did all kinds of things. But what I was really doing was writing. That was my real work.
And it was 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 and I sort of always thought like. OK, my my first novel will, of course, be published and done and everything by the time I'm 30, but I, I just said, OK, I was I was approaching 30.
I was like, OK, 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 to you know, it's hard to have that kind of time and focus when you're working full time. So graduate school kind of solve that problem for me. And I only looked into I only applied to graduate schools that, you know, with the idea that I would only go if I were offered a full a full fellowship or scholarship and tuition remission and that it wouldn't put me further in student loan debt 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?
What Changed? Yeah, well, you know, 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. And, you know, all of this. I just thought, I can't write another book. And what happened is I started writing and then it went on and on and on and on.
And I was like, oh, I have a bigger story to tell. And it really I didn't know that until I was doing the writing because I found the bigger story when I was writing and buy the bigger story.
I mean, the story that exceeds the kind of like, oh, here's you know, here's my interesting journey or here's the big loss I suffered, you know, that that I knew that I needed to find a universal thread that the my journey and my loss and my experience would be had the potential to be expressed in a way that other people would see themselves in it. And it took some writing for me to to figure out how to do that or to figure out that that was there.
You said that being a memoirist is about learning how to re-enter previous versions of yourself. Yeah. How do you go back into that previous version while still maintaining who you are? Well, you know, you enter the magic of writing, that's that's what's so cool about it is so what I mean by that is this is 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 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, you know, beyond her explanation, had to trust herself to do that. And so I went in and reinhabited that and and as I was writing, for example, that scene in Wild, where my husband and I are decided to get divorced and then we get divorced and we're saying goodbye to each other.
You know, 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 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, you know, 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, you know, 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.
And it's very emotional in the book. I'm crying, you know, I'm like, it's sad. And then, you know, I'm standing there with Reese Witherspoon right before she's going to walk into the street with Thomas Sadosky, who plays my ex-husband. And they're going to begin shooting the scene. And she suddenly looks at me and she just 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 comfort me.
Wow. And I thought, oh, OK. I, I it was so clear, crystal clear to me because I was watching that scene and I wasn't crying because it's not sad anymore. But when I watch the scene of my mom dying. I cried, Oh, that feel sad 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 sorrow. Our sad in the moment and others are sad forever.
And, you know, 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 I you know, 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, you know, I had to make a decision that caused me and another person pain, but I'm better for it.
And it's not sad anymore. It was it was actually the the golden key that opened the door to to my liberation. And there was loss in that. But but there was more game, you know, it became a gift in the end. 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.
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. Yes.
And I also thought it was interesting that, well, you were writing Dear Sugar, you were giving people advice and in wild you weren't. But people have read it that way. And I'm wondering how you feel about that, that whole sort of notion of advice giving. I know you've referred to self-help work as intellectually mushy.
And and and I think 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.
Yeah. When I was writing, while it never occurred to me that anyone would be experienced as inspiring, you know, I was really just trying to write the truest Rozz realist. Story about that experience, about my grief, about my finding my way on this long walk, about the experience I had in the wilderness, and so, yeah, people do experience that in a in a like, well, what's the message of wild?
I'm like, oh, you know, the message is whatever you think, whatever truth you find in yourself when you read it.
That's what I meant.
When books are my religion is I felt saved by them like I felt seen by them. So, you know, to me I'm always sad. Like in airports, there are many of these kind of little convenience stores and airports will have these little turnstiles that are there, like inspirational or self-help like that. And there are no books. There's never like novels there. There's never, you know, 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.
And I find that the most helpful literature when it comes to like what real self-help is, is things like, I don't know, Jane Eyre, you know, Alice Munro.
Short stories. There I am. And Alice Munro, short stories. There I am. And Toni Morrison's beloved. There I am.
And you know, Mary Oliver's poem. So, yeah, you know, I didn't intend for those things to be self-help and frankly, even sugar when when tiny, beautiful things came out, I was like it was in the self-help section of any. So I was like, what? What? So I think of myself as an accidental self-help writer because of course, of course, dear sugar columns are self-help. And yet what they also are is literature.
I understand you've been at a sort of crossroads now is different opportunities have come your way weighing the reasons to do it, weighing the reasons not to do it.
And you've stated it's not about the number of things on the list. It's about the weight of those things. And 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? And I wanted to see if you can help me understand how to know when something is the thing you really want to do.
Oh, gosh, again with a heart. So for me, that Deep is 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. So if I 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 that becomes also something that is meaningful to others, that's a big thing to contribute to the world.
And I think that for me. That sense of like rightness or a sense of like if this mission is fulfilled, will it extend beyond my small little life? Like I feel that as I feel that as a sort of powerful call.
Cheryl, I have to ask questions for you. OK, the first is something that I was really heartened to read about.
I understand that sandwiches are problematic.
Of course they are. Sandwiches are just like chaos. You know, machines, right? They're just like willy nilly. See, I know you're my sister. I know you that I know you also feel this way like I have to be orderly.
Absolutely. Everybody has to be perfect.
Not only do they have to be orderly. Yes. That's the whole goal of a sandwich for me is to make every bit as much like the previous bite as possible. OK, consistency. So you put the you know, whatever whatever you're putting on it, it has to be uniformly applied everywhere. Burrito's also sometimes have this problem. If people don't do the burrito correctly, it's just tacos.
Yeah, absolutely. Yeah. So this is my last question, Cheryl. What is the thing you want to do most next? Finish my next book, I really am ready to do that, so wild and tiny, beautiful things were published within four months of each other in 2012, and basically my life was just an absolute you look like it was just like a volcano.
And I was, you know, movies. I was on the gurney and. Yeah, and the play.
And I was involved in the podcast and the public speaking career and also the kids. You know, during all this time, I hear these, you know, little heads, you know, and who now are 14 and 16. And I just feel like, wow, OK, I really now I'm 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 as scared at all the things I am when I'm writing, which means I'm writing my next book, I can't wait to read it, cannot wait to read it.
Thank you, Cheryl Strayed.
Thank you so much for joining me today. And design matters into an open mind. So many wonderful things to say. Thank you, Debbie. You are. You are a woman after my own heart, I swear. We have to meet in real life someday day have sandwiches. Absolutely. I would love that. I would love that. Thank you, my dear. This is the 16th year in broadcasting design matters. And I'd like to thank you for listening.
And remember, we can talk about making a difference. We can make a difference what we can do. Both named Debbie Millman. And I look forward to talking with you again soon.
Special thanks to the sponsor of this episode. Hoffler and Co Design Matters is produced by Curtis Fox Productions and on Pandemic Times.
The show was 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 Petitt, and the art director is Emily Weiland PUREX.