Wild Ideas Worth Living Transcript: Cheryl Strayed


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Shelby Stanger: This is episode 76 with author and hiker, Cheryl Strayed. Welcome to Wild Ideas Worth Living, an adventure podcast presented by REI Co-op, the brand who helps you get outside through gear, classes, and adventures. We talk to experts who’ve taken a wild idea and made it a reality so you can too. From people who have climbed the tallest peaks, started thriving business, and even broken records, some of the wildest ideas can lead to the most rewarding adventures. I’m your host, Shelby Stanger, and I hope you enjoy the show.

Cheryl Strayed is the author of the number one New York Times bestselling memoir, Wild, about her trek across the Pacific Crest Trail. It became a hit movie starring Reese Witherspoon. Cheryl is also the author of the New York Times bestsellers Tiny Beautiful Things, and Brave Enough, as well as the novel Torch. Cheryl hosts the Dear Sugar column and Dear Sugar podcast on the New York Times. She’s a true force of nature.

I’ve wanted to interview Cheryl forever. We talk about everything from hiking to riding, how to stay healthy, life advice, and so much more. This is a longer episode than many, but we’re taking next week off because, after 76 episodes, you got to take some breaks to live more wildly. Please note, that we also shortened one popular slang word on this show. I hope you enjoy it.


Let’s just start with hiking. How does hiking and outdoor adventure fit into your life right now? Now you have kids and family, and you’re busy. What does that look like for you right now?

Cheryl Strayed: It looks like that I do it every chance I can. It is really the thing I love to do most when I have time to do things. I also go out of my way to make time to do that. I have a son and a daughter. My daughter is 12, and my son is 14. They know on Mother’s Day and my birthday, we’re going to be spending that day hiking.

A couple of years ago, my daughter gave me a Mother’s Day card that she made for me. It just said, “Mom, I love you so much, I’m willing to go hiking with you,” which really cracks me up. I also really want to share that sense of adventure with them, and especially my favorite form of adventure is hiking and backpacking.

What’s cool is when they were younger, I sometimes had to bribe them a bit. “We’re going to walk for 15 minutes and then you get three gummy bears, and then we’re going to walk another 15 minutes and you get three more.” That worked. Now, what’s happening is my kids are starting to actually love hiking on their own. That’s just, to me, one of the greatest most fulfilling things as a mom, to see them really engaging with the sport.

My husband and I took our kids out of school last fall, and we traveled around the world. Our first stop was–

Shelby: Wow.

Cheryl: I know, it was so fun. We went to New Zealand, Nepal, Tanzania, Kenya, and Portugal, with a stop in Qatar and Singapore along the way. The first thing we did is we went and hiked two trails in New Zealand in the Milford Track and the Routeburn Track; went back and it was so great. Here I was, concerned about my kids because I was like, “Are they going to be cool with carrying packs and hiking all day every day for several days?” What was funny is they absolutely left me in their dust. [laughs]

Shelby: Do you have a favorite hike that you love to go? You live pretty close to part of the PCT now, if you’re in Oregon. I remember there’s a place pretty close by.

Cheryl: Yes. I live in Portland, Oregon. I’m really just a little bit more than an hour’s drive from the Pacific Crest Trail. I hike on it regularly. There are so many trails in the Pacific Northwest. Even in my own city, we have Forest Park which is this beautiful park that, really, there are parts of it that are like, “Wow, I feel like I’m in the wilderness,” even though the city is just a mile away; the Wild Wood Trail and a whole web of trails in that park that I use regularly. Also, we have our beautiful Columbia River Gorge. There was a major terrible-

Shelby: Fire.

Cheryl: -fire last summer. A lot of those trails are damaged, but not all of them. I was with my family recently on one of those trails. I was glad to see, not everything was destroyed by that fire, thanks to all the people who fought it and contained it. Those are really my go-to places.

I also really love this idea of thinking about discovering trails in different parts of the world. I’ve traveled to many countries. Everywhere I go, I try to find a trail to hike.

Shelby: That’s so cool that you still love hiking. What do you think of all the people hiking the PCT now? It’s taken off. I’m interviewing even Aspen Matis who wrote a book that was inspired by your book. So many people have this journey of doing these thru-hikes now.

Cheryl: I think it’s beautiful. I’m so honored that some of those– at least some of those people, some portion of those people, were inspired to go hike the trail by me and my book. I think that the most important thing when it comes to hiking that Wild did, is it gave a lot of people permission and confidence. I didn’t go out there knowing everything about backpacking when I began backpacking. I made comic hay of that in the book.

It’s not so uncommon. Most people, when they engage in any sport, you learn the hard way. You learn by doing, and you realize, “Oh, jeez, it actually matters how heavy my back is. That actually has an impact on my hike,” or it’s harder. To this day, what I’m always intrigued by is that hiking is always harder than I think it’s going to be.

One thing, I wrote about this actually in Wild, that even by the end of my hike, I was saying, “Wow, this trail still humbles me.” It still, even on an easy day, by the end of the day I’m often like, “Okay, that was– There were parts of it that were quite challenging.” I find that to be true always with hiking, that I’ll think, “I can hike 10 miles. no problem.” Then, at mile nine, you’re like, “One more to go,” or, “Here we go up this mountain, or down this mountain.”

That’s what I love about hiking, that you’re always humbled and engaged in a new challenge. There are those rare times that it is easy, it just feels like a gift.

Shelby: You did it when it was a lot harder. Now, there’s some really nice ultra-lightweight gear. If you could do it again, is there anything you’d take now that you didn’t then?

Cheryl: No. It’s an interesting question. You’re right that it’s a different world. I hiked the trail in 1995. I think sometimes people forget that, that I was literally writing about a different world. It was the world before ultralight. Backpacking was really known by many people. It was beginning. It was certainly in the air, but it wasn’t really the emphasis.

Also, there wasn’t the internet. It existed, but most people weren’t using it. It wasn’t like you could log on and find all of the information you can now find, and all the community about the trail, and long-distance hiking in general, the PCT in particular. I did do things the old-school way on the trail in ’95. It’s changed a lot.

When I look back and people ask me like, “Would you take something different? Would you not take something?” I have to say, I’m glad that I did the hike the way I did it because, even the stuff that now I recognize were mistakes, like I should have had bigger boots that fit better, or I should have taken less stuff, I really like that I learned the lessons I did the way I did it, even though I do it differently now.

Shelby: What do you love now? You take gummy bears to bribe your kids as they were younger. What else are good tricks?

Cheryl: I’m a lot more mindful of the consequences of weight. I think that part of that is made easier by a couple of things. The times. There are more lightweight things to take backpacking. There’s a lot more consciousness and mindfulness in that direction in general among the backpacking community, and also the gear we take.

I also think that it helps that most often now, I hike with other people so we can spread out some of that weight. One of the things that happened to me in 1995 when I was going solo is you have to carry literally everything. There’s no sharing of some of that gear.

Almost always, this is true for me whether I’m traveling on an airplane, on a business trip, or on a backpacking- hiking on the backpacking trails, I’ve always tried to remind myself that I hardly ever need all the clothes I think I’m going to need. I always try to get those clothes arranged on the bed, and then cut it in half and don’t take everything I think I need. You do end up almost always being able to wear those things over and over again. They might not smell great, but you can wear them over and over again.

Shelby: That’s good advice about life; just going lighter. I love that. We get a lot of questions about people just wanting to do something wild, whether it’s a journey on land as a thru-hike, or it’s a giant surf trip, or a paddle across somewhere. How do you advise one on how to choose which adventure they should take, especially if they’re at some sort of crossroads or transition in their life?

Cheryl: First of all, the most important advice I have for anyone who’s interested in doing something big, is to do it. If you have that impulse, do it. See it through. Do it in the near future. Do it as soon as possible because life does have a way of giving us a lot of reasons not to go on to that big adventure, that big trip. Make it happen.

I’m such a fan of list-making. When I’m at any kind of crossroads, or I’m torn between this or that, is I make a list of what are the positives of this scenario, and what are the negatives of this scenario, and then compare those things.

For example, I love land. I’m not really a water person. I love to swim, but I’m not ever going to probably be somebody who’s like, “It sounds really great to me to sail around the world.” It actually doesn’t sound great to me, but walk around the world sounds fantastic.

You have to really think about it. What are you drawn to? What do you like to do? What are your preferred, not just activities, but landscapes and environments? Are you somebody who is really excited by the idea of going into really cold places, or really hot places? Are you a mountain person or a desert person? What’s cool about trails like the PCT, you can in both mountains and deserts. You don’t have to choose. What I’m getting at here is really assess what you’re drawn to on every level, and make your choice based on that.

Shelby: These list, this is interesting because I’ve heard you talked about this on another podcast before. You’re a list-maker. Now, when I make a list, usually I get so in my head that the list doesn’t work, and it’s an answer that comes in nature. I’ll be surfing and the answer will come to me because– For example, quitting my job in 2009 made zero sense on paper, but it was this gut feeling. When you make these [sic] list, I think you do it in a way where you address fear.

Can you talk a little bit about that because that’s not something I would do in my list? That’s different and I like that.

Cheryl: What you just said is it made zero sense on paper, but what I would say to that is you put the wrong thing on the page, that you were prioritizing, I think probably other people’s values. Quitting your job is a bad idea because where are you going to get money. That’s the first thing that we all think of, and that’s fair [unintelligible 00:12:48].

That’s not a bad question to ask. I think that so many of us have been so conditioned all of our lives to really honor those financial security, and the things that make sense because they’re the things that other people have done throughout all time. “Go to college. Get a good job. Invest in your career. Meet somebody great, marry them, have kids,” that whole kind of American dream trajectory which fits for some people and not for others.

What I say is revise the narrative. That list is not about the expectations that others have placed on you, whether that be a family, or the culture, or even your own inner critic, but rather, making a list about what is it that really excites you, what engages you, what are you afraid of. Are you running toward that fear or away from it? Are you being ruled by your fears, or are you looking at in the face and saying, “You have something to teach me. Teach me what you need to teach me, fear”?

That’s where I really try to begin that list is what’s in my heart, not what’s in my inner critics, that kind of in-your-head, when that inner voice is saying, “This, you surely shouldn’t do this. It would make so much more sense, Shelby, if you stayed employed.” That would lead you to misery.

Shelby: Thank you, Cheryl. That’s excellent advice. I think it’s helpful for anyone making decisions about anything. I want to know, what books do you recommend, especially for adventurers? A lot of guests who come on this show, they recommend Wild. What books do you recommend for adventurers?

Cheryl: [chuckles] That’s so sweet. I’m always grateful when I see Wild on those recommended books. I’m always honored. I love adventure books. Really, to me, not just adventure, but any kind of travel into the wild, especially, because I think that that’s always something interesting happens. You get to, in some ways, travel along the way on somebody else’s adventure. What books have I been loving lately? One of my all-time favorite books is My Journey to Lhasa. Do you know this book?

Shelby: No.

Cheryl: Written a long time ago by a woman named Alexandra David-Néel. It’s about her 1923 expedition to Tibet. I also love this book that everyone sent me when it came out. Bold Spirit: Helga Estby’s Forgotten Walk Across Victorian America by Linda Lawrence Hunt. Here, again, it’s like a walk by somebody a long time ago, 1896. She was a Norwegian immigrant, and a mother of eight children, and was just basically in dire straits. Do you sense a theme, here? I love these women who are like– [laughs]

Shelby: Did you read Tracks? The woman who crossed–

Cheryl: Tracks by Robyn Davidson is a great one too. I actually did an event with Robyn in Jaipur, India. We were interviewed on stage together. It’s about her trek back– When did she do that? Was it the ’70s or ’80s, across about 1,700 miles in the Australian Outback? I love that too. I also love this woman. Have you ever read any books by Helen Thayer?

Shelby: I don’t know. I don’t think so.

Cheryl: She’s an adventurist as well, and a walker. She’s written a few books. I don’t know how many, maybe, even many books. The one of hers that I read and really just loved is Walking the Gobi. It’s about her 1,600-mile trek across Mongolia. She did that when she was 63. She was with her 74-year-old husband. They’re, wow, aspirational. That’s what I want to be doing when I’m 63.

Shelby: Is that really what you want to be doing at 63? What else adventure-wise, outdoorsy do you have left on your bucket list?

Cheryl: Gosh. It’s interesting when you just said, “Is that really what you want to be doing?” Yes. Is it just hyperbole that I just said that, or is it true? I think I would love to do that. I do think that I would really like to sleep in a bed.


Shelby: Me too. I like that better than tents.

Cheryl: I’m going to be honest. I want to be perfectly honest. One of the kinds of long-distance walks that have become appealing to me, and your listeners who are backpacker [unintelligible 00:17:23] will be like, “No.” These things where you got to hike inn to inn. I think the next long walk I really want to do is I would love to walk across England or something. I understand I haven’t done long-distance walks in the UK, but you can stay at an inn, and have dinner at a pub and have a glass of wine.

There’s clamping, but what’s the word for luxury walking?

Shelby: I don’t know. My fiancée calls me a Gucci adventurer. I like that too. We’ll go on really giant runs and walks, and I’ll uber home. He’s like, “Really?” I was like, “Yes. I wanted to get 20 miles in, but one way.”

Cheryl: You want to uber home? I get that. In New Zealand, too, when we went on our backpacking trip, it was like we’re carrying our packs and we’re hiking the miles, but we got to stay in these little inns, these lodges along the way. Somebody else cooked you dinner which is wow, what a way to go.

Shelby: I did the Amazon River. Someone set up our tent and cooked us dinner as well. It was the Amazon. It was scary, and there were these things underneath us. Enough of the adventure was adventurey and scary that sometimes a little comfort is good. I’m all for that. I love this idea. I think you should do a castle walk in Europe where you walk and you stay at castles.

Cheryl: Yes. Have you done any [unintelligible 00:18:44] in Europe or France?

Shelby: No. That’s next.

Cheryl: One thing that’s very intimidating to me about Europe is, man, they are hardcore when it comes to hiking. Many of their trails are just absolutely straight up or straight down. Of course, there’s always some 60-year-old Norwegian who’s just blazing past you because they’re so fit. They’re fit from birth. They’ve been like skiing and climbing up mountains. There’s just no way that we can hike as fast as them.

My husband and I always- we have a phrase that we say between us. It’s “Remember the Danes” because we once met these really old Danish people who hiked about quadruple the speed that we could hike.

Shelby: Speaking of fitness and the Danes, one of our listeners, [unintelligible 00:19:37] wrote in. They want to know, how do you keep yourself so fit and healthy?

Cheryl: Oh my gosh. I don’t keep myself so fit and healthy. [chuckles] I’m glad somebody out there thinks I am. It’s like everything. I go in and out of phases of my life where I am better at following through with that commitment to my health, and to exercise and eat right and do all the things that I constantly aspire to do.

For me, it goes back to that, again, that sort of daily struggle of asking yourself, putting on that metaphorical list, who do I want to be today, what do I want to do. Sometimes I go through phases of my life where I fail at following through on the list because other things interfere.

When I think about fitness and health, it’s a lifelong commitment. There’s a long view and there’s a short view. The long view is who do I want to be over the course of my life? What are the things I want to do with it? What happens on the micro scale is every day, you have to make that commitment anew. I’m there right now.

Actually, I decided to walk the Portland half-marathon in the fall, which I know that the half marathon, that seems a lot of your listeners are like, “13 miles? That’s not that far.” That’s true. I can walk 13 miles tomorrow if I want to, but what I found is that saying I’m going to do a thing, like signing up for a thing, it helps me keep my focus. Even though it’s not going to be a really hard goal for me to achieve to do that, to run-walk a half marathon, it centers my focus. It, in so many ways, allows me to follow through every day, like, “I’m going to go walk for an hour today because I’ve got to train for that thing.”

Shelby: It’s also a really good tactic because you’re so busy. That’s one of my questions for you. How do you balance time for you in between being a wife, a mother of two awesome kids, and gosh knows how many commitments you have a week?

Cheryl: A lot. I’m writing, and I have the podcast. I have lots of public speaking. I have a too-busy life. The answer to that is I don’t know about balance. I am always trying to attain it. Part of my clarity around it has been to, in some ways, let it go and to say, “This is an era of my life that I’m just really busy. I’ve got lots of things going on. I’m going to do the best I can do.”

I’m not going to be able to tell you by the end of every day that, yes, I chopped my own vegetables, and cooked a fabulous meal, and did an hour of yoga, and went for an hour walk, and wrote for three hours, and worked on my podcast, and answered every e-mail, and on and on and on, had quality time with my husband and my kids. That’s just not true. When I try to make it true, I suffer because every day, I feel disappointed in myself.

Part of being healthy is– again, this goes back to something I said before– it’s saying, “What can I do? I can’t do everything but what can I do? What’s reasonable? What’s a reasonable course of action? How can I attain some balance, maybe not every day but over the course of, say, a month? How do I fit in all these things that are important to me over a long stretch of time?” That’s been my solution, is to try to take a longer view of balance.

Also, that sense of like time passes and there will be other days when I can chop all the vegetables and do yoga a lot. Maybe that’s what I’ll be doing when I’m 63.

Shelby: [laughs] You’ll be chopping vegetables. I’ll be coming over for dinner. I love it. We’re going to take a quick break to hear about our sponsor. When we come back, Cheryl gives her famous advice, shares advice to writers, and also talks about the party she would throw, and so much more. Stay tuned.


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What’s the best reiteration of your famous advice “write like a mother”? What have people taken that into that just totally makes you laugh?

Cheryl: [chuckles] Gosh, so many things. I have signed countless books, “engineer like a mother”, “mother like a mother”. That’s one of my favorites because of the double mother. Really, anything you can think of, people have embraced that advice, I guess, to do things like a mother, which began as write like a mother.

I love that because, of course, that’s what I always intended. It was never a message just for writers. It’s really about going full throttle, giving it everything you have, even if you have doubts. In fact, probably you’re going to have doubts. Do it anyway. Do your best work, and stop complaining about it. Rather, complain about it, but don’t let that be the thing that stops you.

Shelby: I have “podcast and pitch like a mother on my wall”. Thank you.

Cheryl: You do?

Shelby: Yes, of course.

Cheryl: That’s so sweet. I love that. Thank you. I’m honored. I’m always so flattered when people have taken something I’ve written into their own lives and hearts, because that’s what writing is all about. You want people to make it have meaning in their own lives.

Shelby: You give beautiful advice about life, about writing with your Dear Sugar columns, with everything. What advice, right now in our time, are people asking you about the most, and asking for, and how do you respond?

Cheryl: There’s always the love questions. Throughout all time, people have grappled with finding love, and keeping love, and sustaining love, and knowing when to give up on love, and wanting to know what to do about making it last once you have found that partner. I think that’s kind of cool to know that we will always have those troubles.

For me, I’ve always found that to be consoling when I’ve been struggling with whatever kind of issue, I have to think about all the people before me who have been grappling with these same questions. It’s also kind of a bummer because it means nobody’s solved those questions. The fact that I’m not alone in whatever I’m struggling with is the message I’m always trying to give. “You are not alone. I’m not alone. We’re together in this.”

I think that message is especially important right now when people are feeling divided. I think a lot of Americans are feeling very concerned about the level of tension and conflict in our society. It’s right there in the newspapers and on the headlines, on websites and so forth, all the conflict we have. It really has an impact on people’s psyches and personal relationships. That’s coming up a lot in the letters, too.

Shelby: It’s awesome. I put it up on Instagram yesterday for just a couple of hours. I put your picture in Wild and I was like, “Hypothetically, if I were to interview this person tomorrow, what do you want to ask her?” My inbox was flooded, so I had to delete the picture. It was awesome. So many people want to ask your advice.

One asked– So many people on the show want to write and create art, or so many people listening to the show do. I think much of the time what’s the hardest for them is starting. What’s your best advice on just starting?

Cheryl: Let me just say to everyone listening, it’s hard for me to start too. It’s also hard for me to keep going. [laughs] It’s hard to do it. This is connected to what I was saying when I was answering your question about the list, this notion that, let’s see. You quit your job. That means you have no money. That means you shouldn’t do it. Right? Wrong.

I think that so many of us are taught to misread these cues. It’s difficult to start. It feels like when you do start what you’ve written down or created, it’s silly or not as good as you want it to be, so that means you should stop. Right? Wrong. Actually, that doubt, that fear, that anxiety, and even that resistance is a sign to me that you need to do this thing.

You need to keep going, you need to push through those very negative cues that often will stop us from doing what we want to do whether it’d be in hiking or in life. When you’re hiking, and you pass a really nice shady spot, you want to sit down and stay there. At least I do. I know that if I keep going, there is a benefit to that, there’s a payoff to that.

That is also true in my creative life. It’s deeply true in my creative life. I have never written anything that was easily done. Maybe that’s an overstatement there. Maybe there are a couple things that came just bursting out at me, but most of the time, it was hard. It was hard to begin, and it was hard to keep going, and it was hard to look back at it and revise and make it better.

That is part of the creative process. It’s looking at your fear. It’s looking at that challenge and overcoming it.

Shelby: Is there something, though to the feeling that when you’re meant to do it, it does come a little easier? I just remember hearing you at Warwick’s in La Jolla years ago. I think you were reading from Tiny Beautiful Things. It was a long time ago, and I said, “How long did it take you to write Wild?” It wasn’t that long?

Cheryl: You’re right. I wrote the book in a year or two. It seems long because two years of working or writing like that is intense and hard. The book before that, my first book, Torch, took me more like seven years to write. In those couple of years, I was writing Wild, there were so many days of fear and resistance, and even sometimes a month or two at a time that I didn’t do any work at all.

I tend to be a binge writer. I would maybe go a month without writing, and then I would spend a month doing almost nothing but writing. Even though I had two little kids, every spare moment, writing for hours and hours a day, and not sleeping very much, and just working really hard. Those two years were really hard work, but yes, you’re right, it was pretty quick.

Same with Tiny Beautiful Things. That book was written as I was doing the edits on Wild. Week by week, I was writing this column for the Rumpus, and I accidentally wrote that book. That doesn’t mean it came easily.

Shelby: I love that. I think what’s interesting is you’re– A lot of the recent writers I’ve interviewed are binge writers. That is so refreshing to hear because I think I read the War of Art, and he says ”show up and do the work every day”. I went to a coffee shop for an entire year at 5:00 AM every morning, and I sat on my computer and try to write a book. I did, but I didn’t like it and I killed it. It just didn’t feel authentic.

Today now, I approach writing so much differently. I won’t write for months, and then I’ll go and I’ll just write for like three days straight. That just feels much more authentic. In all creative aspects, is that the approach you love to take this–? Some people are just busy. That makes more sense.

Cheryl: For me, again, another really liberating lesson that I learned as a writer is I had that similar instruction like, ”you are not a real writer, if you don’t write every day”. That’s absolutely false. I think that there’s no one way to be anything. Certainly, there’s no one way to be a creative person, to be a writer. You have to make this work fit into your life, you have to make decisions and follow through with them and be disciplined, but those decisions have to be reasonable.

I’m probably like a lot of your listeners; always aspiring to eat healthier, or exercise more, or do this or that. Il be, sometimes when I’m extreme, like, “I’m going to eat only vegetables for the next 60 days,” or whatever. By day three, you’re like, ”Give me a glazed donut, please, three of them,” because you’re just like this is not realistic, but what if you do make a realistic plan about your diet and it’s eat some vegetables every day for 60 days, or whatever that is.

It’s the same thing with our creative work. It’s saying, “I can’t write every day right now, because I work full-time, or I’m with my kids nonstop on these days,” or whatever it is, whatever things are in your life, “but here, I can work all day on Tuesday next week. I’m going to make sure to protect that day so that that’s what I can do.”

That’s what I always want to tell people who want to be writers is make a plan and follow through. Even if it’s a modest one, even if it’s like two hours a week, trust me, you’re going to get lots more writing done doing that, than you would if you just sit around and whine about how you wish you could write but you don’t have any time to do it.

Shelby: [laughs] I love that. For those who do want to get their work in the world, there’s a lot of options. There’s just a lot of media. There’s podcasts, blogs, books, so many different outlets. How do you advise on where to get your work in the world, and knowing where you should?

Cheryl: I think that just because work can be in the world, it doesn’t mean it should be. There’s something really very much I value as both a creator and a consumer of other people’s creations, is an adherence to craft, and an adherence to a value system that says, it matters to me that I do really good work, and that I go through a kind of rigorous apprenticeship, essentially.

I always say that’s the most really rewarding piece of making art, I think, or writing or any other– It’s the creation. Play around with that. Go into the metaphorical woods with yourself for a while before you step into the meadow and show everyone your great thing. When you do, there are, as you say, so many options.

I love that the podcast world has taken off. I have a podcast too. Everyone I know, has a podcast. It’s pretty cool. When it comes to writing, the other thing, and probably podcasting too, it’s always nice too to have other people’s opinions, people who also have some expertise. Certainly, I’m always grateful to have editors who are saying, ”This piece, you can do a little better. That part didn’t work.’. Same with my podcast, I love that I have a producer who can really help bring that conversation that I have on my podcast to the next level through her production, essentially.

Shelby: I love my editors and producers. Social media is another way people tell stories. It can be pretty weird, but it can also be pretty positive. I saw on your social media that you take your kids to protests. We talked about your kids, and they just seem really cool. A lot of kids today, they’re just really cool, really aware. What do you think of this whole new youth and student movement?

Cheryl: My kids have participated. They’ve been to many protests in their life. My husband and I have always raised them with a social conscience and a moral obligation to be active citizens in this democracy, and they are. It’s really cool to see them really stepping forward on their own now in response to the student movement that began with the March for our Lives and continues. I’m really proud of them and supporting them.

I’m not a religious person, but I really have a lot of belief that we are all divine. I’ve always taught my kids that kindness is the most important value that I hold. That’s the thing I want them to be when they grow up is kind. I don’t care if they’re a doctor or a lawyer or whatever. I want them to be kind, and they know it.

I love that they’ve carried that into their lives and into their school. Their school did a walk-out. Portland public schools, to their credit, was really supportive of it. I thought that the schools did a great job supporting the kids in there and making this– expressing their first amendment rights; really making their voices heard.

Shelby: I love that. I love talking to young kids today. It’s really refreshing. They’re really smart. They’re really engaged. I think this whole movement has been really eye-opening to a lot of people who traditionally judged millennials and younger people differently.

People come up to you, I’m sure. I even saw it at one of your book signings. They come up to you. I’m probably even acting like this, like we’ve known you forever because you’ve poured your heart to the world. I’m sure people come up to you with dire questions and needs. How do you deal with that responsibility?

Cheryl: You mean how personally, how do I kind of hold [crosstalk]?

Shelby: Yes, even when people email me and say, “Hey Shelby, what do I do with my life?” I’m like– [chuckles] I don’t have it totally figured out. I’m getting by on my own. I’m just doing what I could do. I liked your advice; be kind. I think that’s the answer to many questions, and solves many problems in life.

I’m just wondering how you deal with the– You just have it on such a different level that I can’t even imagine. How do you deal with that?

Cheryl: I also just have it explicitly on my podcast, the whole point– “Write to me and tell me what terrible thing you’re experiencing and I will try to help you.” It’s actually part of my job. Certainly, in all my books, even though Tiny Beautiful Things is the one that’s explicitly advice, I think that people really read my other books very personally too.

I can’t tell you how many people have said, ”Wild saved me. Wild saved my life.” That’s also true even if my first book. This didn’t begin for me with Wild. My first book, Torch, which is a novel, it’s fiction, and even through those fictional characters, people were responding on an emotional level seeing themselves in it.

It’s been a years’-long practice of learning how to hold other people’s sorrow and loss. The way that I’ve come to think about it in my life is that it doesn’t feel like a burden to me, because they are almost always when they share their stories with me, saying that I’ve already helped them. I do think that hearing other people’s stories of loss and confusion and struggle is so helpful to just have them know that somebody else can stand there and bear witness to what they’re holding, and to help them hold it too.

It’s kind of like being on the scene of an emergency. It’s more stressful to stand there and scream than it is to help, to put your hands into the effort of saving somebody’s life. I think of my books as doing that. My podcast is doing that too. Nothing I write or say is going to take anyone else’s sorrow away, but it will make them feel, perhaps, that they’re less alone in it.

It will remind them that life goes on, and that almost all of us have wounds. Those wounds eventually become something else if we apply some effort to healing them; something beautiful instead of something ugly.

Shelby: Any advice on just being a better listener? You’re so good at it.

Cheryl: Thank you. Wow, that’s an interesting question. What you’re asking, obviously, the literal technical answer is just shut your mouth and listen. I think the actual thing you’re asking is how do you listen with compassion?

Shelby: How do you show it, too?

Cheryl: Often, we’re sort of hardwired. We’re taught like this is good and this is bad, and this is acceptable, this is unacceptable and this is a deal-killer and that is not. What that does is it boxes us in and makes us feel really ashamed when we have made a mistake or been the person who did “the wrong thing”, and shame almost always is isolating.

As a listener, when somebody tells us something about themselves that maybe is not so flattering, we feel like our job is to, in some ways, judge them. What I try to do when I listen to people and when I read their letters for the podcast, is to hold them in unconditional positive regard. That is to say that my job is not to make a judgment about whether you’re right or wrong, or you did the bad thing, or you’re good or bad, any of that stuff.

My job is to listen, hear the story, and try to illuminate it in some way, try to offer some words or some way of thinking of the problem or the experience that is sort of beyond what that storyteller, that person talking to me or writing the letter can see or hear or perceive right now.

Listening, really, is about saying, “Here–” It’s making the story. It’s receiving the story and then sending it back to the person in a way that isn’t, in some ways, illuminated or broadened or deepened. I think that’s about not being judgmental. It’s about not making that your first order of business of determining whether somebody’s good or bad, or right or wrong.

We all know that we’re flawed as humans. We all know that we’re complicated. Nobody’s all good or all bad, or at least very few of us are. The best people in the world have made mistakes that are really very harmful and sad. We all have. I think that the closer we can get to acknowledging that as individuals and as a society, the better off we’re going to be.

Shelby: What do you look for in mentors? Who are your mentors today?

Cheryl: Kindness. I think that I’ve never learned anything much important from anyone I thought was a bully or nasty or mean. I mean kindness to everyone. I’ve had the fortune of having people like that in my life. When I was in graduate school, I got my MFA at Syracuse University. The writer, George Saunders, was my mentor. He is an extraordinary human. He’s a great writer. He’s also a great person. He’s such a model for me in that regard. Those are the kinds of people I admire.

I’ve never been a person who looked to one person to teach me the lessons. I don’t have many mentors when it comes to like this one person who I’ve followed over several years and they taught me how to be, but rather, I’m always learning other people. I think that’s a powerful thing to just learn lessons that are offered up to us in our lives all the time, and they come from all directions.

Shelby: You’re also buddies with Oprah?

Cheryl: Oprah has been great. I was just going to say one of the things that Oprah- that I’ve always been so impressed with her is the first time I met her, she was nervous and excited to meet me. I was just like, “What?” I could just see in her eyes that I think that she was excited like that. I was like, “This is Oprah. I’m the one who’s supposed to be nervous and excited.” I was nervous and excited.

What I saw in her was her vulnerability. I saw in her that she hadn’t forgotten that she’s a human. She didn’t believe her own breath like, “I’m the diva. I’m Oprah and so everyone has to kiss my ring.” The minute you are moving through the world that way is the minute you just lose your own humanity, and that you do stop learning from people.

I’ve never been at risk of doing that but, boy, seeing the way that Oprah does that, I was like, “Yes, that’s who I am and who I want to be.” She is a wonderful mentor to me in that way. We’ve had many talks. We’ve become friends since that first conversation, and she’s giving me lots of good advice about– Especially, she saw as Wild was putting me in a different kind of spotlight, l I was like, “Whoa, I don’t know how to be quite so public. How do I do this?”

Of course, I am somebody who puts– My vulnerability is right there for public consumption. I tell you the intimate stories of my life, and I don’t really shield that behind much. Oprah does that, too. We talked a lot about how to do that without losing yourself.

Elizabeth Gilbert was also extremely helpful to me in this regard. She and I had some pretty important email exchanges at a time when I really needed her advice. She was right there for me and with me. I’ll always be grateful to her for that. I wouldn’t say that she was my mentor, but she was a real sister to me in that old classic sense of that feminist idea of sisterhood. She was that to me.

Shelby: Can you share some of that advice? I’m still fascinated with being a writer and hiker, those are kind of introverted activities, but you’re so public. What kind of advice did they give you about that?

Cheryl: I think that idea of the writer as introvert, I think that’s been maybe a misperception of what writers are, or maybe even what introverts are. I am such an extrovert. I even say on my social media my description of myself is an extroverted hermit. It is that on my handle on Instagram or whatever. I’m an extroverted hermit. I am.

I love to be alone, but I am not an introvert by any stretch. I get lots of energy from being in community, and talking, and being public. I’ve always been outgoing like that, and yet I just love to be alone, and I need to be alone. That’s where I really get my energy, too. It’s from both places.

What it comes from is when I think about the work that has been the most meaningful to me, the kind of art I love, the kind of person I love, it’s that work that is honest, that is bold when it comes to exposing the emotional life. I’ve always been curious about the deepest most personal intimate things. Always. It’s been like my lifelong obsession. As a writer, I want to make that for you. I want to make you the best thing that I like to consume. I always knew I had to be fearless in that regard in my writing.

That comes with the price. In some ways, it makes me open. When people want to write really mean things about me, and they have, they can write mean things about the things that matter the very most to me. They can mock me, they can mock my grief over my mother, they can mock my sex life, they can mock the decisions I’ve made about myself in every way because I’ve put them out there for public consumption.

Really, it’s a very small portion of what I’ve received in response to my work. Most people, what they say when they encounter somebody like me who’s willing to really show herself, is they say, “Wow, me too. You said this thing about yourself that I’ve never heard someone say. I thought I was the only one who felt that way, and thank you.” That, to me, is so much more powerful and interesting than any negative thing that people have to say about me.

Part of my coming to terms with who I was becoming in the public eye through Wild, and Dear Sugar, and so forth, is that I had to accept that not everyone was going to love me and that was part of the deal, and it was okay. I’m not defined by the people who love me or the people who hate me. I’m defined by myself. It was a mighty lesson to experience that, to really recognize that through these last few years.

Shelby: That’s helpful. Of the 200 positive comments, if I get one negative one, even if it’s about a guest and not me, it’s hard. I think you just said that the negativity is really just not interesting.

Cheryl: It’s not. What it really is, is it’s so much a projection of the person themselves. I’m not saying, obviously there’s room for critique. I’ve never ever, ever thought that everyone has to love my books or my podcast. There’s nothing that’s ever been done in the history of things that have been done that everyone has loved. It’s not about that.

It’s about do people go out of their way to be nasty to you. If the answer to that is yes, that is a story that they’re telling themselves about themselves. It really has nothing to do with you, but it’s hard to remember that because I know. I feel the same way. When somebody says something mean to me on the internet– the internet gives lots of opportunities for people to do that– it stings. My advice to you about that is do everything you can to just avoid it. Don’t go to the dark places where people say mean things about you.

Shelby: We hit ignore and delete. We usually ask people what would you tell your 15-year-old self. That’s just a vulnerable time in high school. One of the people who wrote in, Lauren Woods, said, “What advice would you give to your 20-year-old self?”

Cheryl: [chuckles] My book, Tiny Beautiful Things, the title of that book is taken from the title of one of my Dear Sugar columns Tiny Beautiful Things. The entire letter is a letter to my 23-year-old self.

Shelby: I read that last night. It’s so good.

Cheryl: Thank you. It’s all in there, but there are various, as you know, different aspects to it. I think that the overall message of that letter is that it’s going to be okay, that even the mistakes you make are actually, in the end, going to be things you’re grateful for because they’re going to be things you learned from.

All of those experiences, the good and the bad and the complicated and the simple and the beautiful and on and on and on, they’re all going to be the things that make you, those things, as I wrote in that column, are your becoming. Your job is to take all of that and make something good of it; to mix all that together in the giant bowl of your life and bake a pie, a really good one that you can eat after hiking a long way.

Shelby: This is the other question we ask all of our guests. If you could throw any party, where is it? Who’s coming? What are we eating? What are we drinking? What kind of music’s playing?

Cheryl: Are you kidding me? This is so fun.

Shelby: Yes, and what activities are we doing? I feel like this question tells me a lot about– it’s just fun, yes.

Cheryl: What are we doing? Shelby, you are definitely there. You’re number one on the guest list.

Shelby: [laughs] My listeners hate me now, great.

Cheryl: [laughs] No, it’s good. We would have so much fun. Where would it be? I know I talked about hiking in New Zealand. That’s my new world crush. We’re going to go to New Zealand. We’re going to have an amazing party somewhere beautiful in New Zealand. I sat on the Milford Track on the South Island. It was really the only place I could go that you can actually just drink water out of the streams, the lakes, which was just amazing. Just dunk your water bottle and then drink. That was amazing.

Let’s go to New Zealand. Maybe we can be on the beach. The land people could hike on trails along the beach and up into the mountains. The water people can surf and swim and frolic, and get eaten by sharks and whatever they’d like to do there. There have to be cheeseburgers because I love me a good cheeseburger; lots of salad and fabulous grilled vegetables and maybe some salmon. Are you digging it?

Shelby: Yes, I’m totally digging this. I’m so over being a vegan. This sounds amazing.

Cheryl: Lots of wine and cheese. I love cheese. I’m just so into cheese. All the kind hearts get to come. The rule of the party is nobody’s being mean to anyone, and we’re all just going to savor and accept each other and love each other for who we are, and listen to the stories that we each have to tell with nothing but kindness in our hearts.

Shelby: I love that. Is there a music?

Cheryl: Of course, there’s music. Let’s see. What will it be? We need to have somebody, some fabulous lovely band. Who will it be? Maybe Lucinda Williams can come and sing to us.

Shelby: I love that. I’m coming. I can’t wait. We talked about New Zealand a little bit before this podcast, so the audience is curious. New Zealand’s just pretty magical. If you could fly an eco-friendly plane– We like to make an eco-friendly, because it’s the kind of show it is– and it could have one of those little banners right now today, what’s your message to the world?

Cheryl: Yes, we need more of those. We need more eco-friendly compliance. That’s a dilemma, isn’t it? I love to travel. That’s just one of my favorite things to ever do. I edited Best American Travel Writing this year. That will be out this fall, and I loved it.

Shelby: It’s awesome. I love those books.

Cheryl: I know, yes. This one coming up is going to be extra good, because I picked all the things I love. The airplane, that the non-environmentally just distracted airplane would have a banner behind it that said, “Keep walking.”

Shelby: Cheryl mother-F-en Strayed, that was epic. Thank you so much.

Cheryl: That was so fun, Shelby. It was really fun hanging out with you on my microphone here.

Shelby: [chuckles] You know you’re awesome.


Thank you so much for listening to this podcast. Cheryl, thank you for sharing your heart and soul with the world through your words, your books, your movie adaptations, and your podcasts. You can find more about Cheryl and buy her books at cherylstrayed.com. You can also get her books at REI. Cheryl we’re supposed to go surfing, so don’t flake.

Thank you to my team at REI, Chelsea, Joe, and Paolo. I totally appreciate your help and support. To my producer, Annie, social media manager, Kayla, you guys rock. To all of you listeners who posed questions on Instagram, thank you so much for writing to me. I did my best to morph all of your questions together and get as many in as possible. I really appreciate it.

I’m going to list a few of you who wrote me. There’s HikingHan, Mada Sayano. Second the road, DelilahLaRow, MicheFish49, RainChild, TlGala, Mad Hirsch, Rachel 62, Haden Williams, SoCal Runner Gal, They Call Me T, Steph Jagger, ValerieSnowflake, ActionSportsLaw, Lisa Benoist, SporadicSojourns, Susan Renee Bright, Love Maine, Alice Graham, Country Photo Shick, See Baird999. Thank you all so much for writing me.

Thanks to all of you for listening. Remember, the best adventures often happen when you follow your wildest ideas. We’re taking next week off, so hit subscribe on Apple podcasts or Stitcher or Spotify, and listen to the previous episodes. We have a ton of episodes for you to get caught up on. We’ll see a week after next.


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