402: Cheryl Strayed | Creativity, Meltdowns, and Leaving It All Behind

Transcript for Cheryl Strayed | Creativity, Meltdowns, and Leaving It All Behind (Episode 402)

Jordan Harbinger: [00:00:00] Coming up on The Jordan Harbinger Show.

Cheryl Strayed: [00:00:03] This idea, I call it surrendering to my own mediocrity. I said, "Do you want to be a person who finished this book that nobody liked, that nobody published, that sits in your drawer for the rest of your life? Or do you want to be the person who never finished the novel she said she was going to write?" Who always said, "Yeah, I'm still working on it." And as painful as that first thing is to write a novel that nobody likes and sits in a drawer all the rest of my life, I would so much rather be the person and who did the work she said she was going to do, than the person who didn't because she was afraid and insecure and didn't want to have to face the idea of failure.

Jordan Harbinger: [00:00:46] Welcome to the show. I'm Jordan Harbinger. On The Jordan Harbinger Show, we decode the stories, secrets, and skills of the world's most fascinating people. If you're new to the show, we have in-depth conversations with people at the top of their game, astronauts and entrepreneurs, spies and psychologists, and even the occasional journalist turned poker champion. Each show turns our guests' wisdom into practical advice that you can use to build a deeper understanding of how the world works and become a better critical thinker.

[00:01:14] Today on the show, my friend, Cheryl Strayed, after some serious life trauma, Cheryl embarked on a 1,100-mile hike on the Pacific Crest Trail. A saga first turned into a mega-bestselling book called Wild and then into a movie. Wild was actually chosen by Oprah as her first selection for Oprah's book club 2.0. So it's kind of a big deal, kind of killed it out there. She's a bestselling author, amazingly insightful advice giver. You know how keen we are on advice on the show. Hell, a third of our episodes are solely advice. Reese Witherspoon played her in a movie. That's kind of amazing. Today, we talk about creativity, writing adventure, loss, self-discovery. And you all know me, there's no woo-woo crap in this episode. Stay tuned after the show because we've got some writing exercises from Cheryl as well, that I'd love to share with you. Let's get into it. 

[00:02:00] If you're wondering how I managed to book all of these great authors, thinkers, and celebrities every single week, it is because of my network. I'm teaching you how to do the same thing that is to build a network, whether it's for personal business reasons, doesn't matter. Go over to jordanharbinger.com/course and check it out. Most of the guests on the show, they contribute to that course. They're in that course. Come join us, you'll be in smart company. Now, here's Cheryl Strayed.

[00:02:26] By the way, you might be the only person I've ever had on the show who has a statue in a major city. How cool is that? That's got to be kind of like hashtag life goals right there, right? 

Cheryl Strayed: [00:02:36] It's totally weird to have a statue and I'm deeply honored. I have to say this couple — they're Australian and they really wanted to do this project that was about making a comment about equality because, of course, an overwhelming percentage of statues are of men. And they wanted to in some way address this in New York City in particular. And so they approached me and said, "We're making 10 or 12 statues of women and we would love to make one of you."

[00:03:02] And at first I have to say, Jordan, I was kind of like, "Uh, sure, yeah, like fine with me. Like whatever," you know, I didn't even really believe that this was going to actually happen. And they asked me to send them a photograph. That was something that might be like a cool form for a statue. So I did. And next thing you know, suddenly they're sending me photographs of the almost-finished statue. It was really thrilling and it really happened. There it is. I went and visited it last year. I mean, when you have a statue, you got to go visit it. 

Jordan Harbinger: [00:03:31] Yeah, and take a selfie next to it. Right? I mean, that's the whole thing.

Cheryl Strayed: [00:03:34] I did.

Jordan Harbinger: [00:03:35] Yeah. And go back like every 10 years and do another one. I don't know. That thing will never age, right, kind of thing?

Cheryl Strayed: [00:03:41] That's right. Unlike me, but it was really an honor. I went with my husband and my kids, and we looked at it and I was like, "Wow. Okay," and to stand among all these women. I think though the bigger thing is obviously, I'm thrilled and honored but the bigger thing is that kind of comment that they were making that like women have influenced our lives every bit, as much as men have. And they haven't been honored in that public way. So I love that they're addressing that with their art. 

Jordan Harbinger: [00:04:05] I did notice that when you go to cities that have statues of females, it's like, oh, this is like a goddess, not a real person. Or this is some sort of nameless thing, that's like Justice. Right? And then if it's a guy it's like, this is Bernard Shaw. He lived from these years. It's an actual person. Yeah. 

Cheryl Strayed: [00:04:22] Yeah. Really right about that. And very often it is a kind of idealized. Like the kind of goddess woman, rather than an actual woman who was every bit as complicated as the men who have statutes in their honor. When my son was about four or five, we were walking in downtown Portland, Oregon, where we lived. And he looked up at me and said, "How come all the statues are men?" And it was really an interesting thing to see how early he was observing that. And so it doesn't matter — it really actually does. And of course, not just when it comes to gender but race and all kinds of other things. You know, obviously, what's happening right now, so many statues being pulled down. And I think that it's really important that we think about who is it that we are idolizing in the form of a statue and to have some consciousness about that. 

Jordan Harbinger: [00:05:08] Yeah, I think you're right. I mean, it's something that is for an '80s kid like me, so invisible, these patterns. I suppose that's true for everyone if you grow up with something. It's kind of that old cliche, like, do you need like Gen Z to go, "Hey, why are all the statues men?" "Uh, I don't know because people who died before I was born, decided that that was a person worthy of celebrating," and no one's really challenged to that ever for some reason.

Cheryl Strayed: [00:05:34] Yeah.

Jordan Harbinger: [00:05:34] I think the question that probably everyone has and where we should maybe start is why did you walk 1,100 miles? What's the impetus for this crazy journey? Obviously, you were already a very experienced backpacker and trucker, right? 

Cheryl Strayed: [00:05:47] Not exactly. Not exactly. In fact, not at all. You know, I decided to hike the Pacific Crest Trail for three months, 1,100 miles at the Pacific Crest Trail, because I really reached a kind of bottom or a dead end in my life. My mom had died young of cancer. She died when she was 45 and I was 22 and a senior in college. And I didn't know what to do with my loss and my sorrow was tremendous. And after I lost my mom and I should say my mom was really my only parent. My father, by then, wasn't in my life. He had left my life when I was about six. And my family fell apart. My siblings and I all in different ways fell apart. And I went from being this really ambitious, self-directed, young woman who knew she wanted to be a writer to really feeling like, you know, what was the meaning of life? What was my purpose here?

[00:06:47] And I was in such pain. I turned it inward. Like a lot of people do and I, and I was self-destructive. I was in my early twenties. So it is an era anyway, where you're like, let's just see what we can do. You know, let's see if we can self-destruct. I certainly took that to its limit. I got involved with drugs, with heroin, with really self-destructive promiscuity. And at a certain point, a couple of years into that, by the time I was 26, I sort of woke up — I had that awakening moment and thought, "What am I doing? I'm wrecking my life." And in so many ways, you know, the older mate could look back and say, "Well, I was trying to honor my mom. I was trying to show the world. I love her so much. I'm going to ruin my life because I need to show you that she mattered." And what I realized is that the only way to really honor my mom or the only way any of us honor the people who love us is to become who they know we can be. And in my mom's case to become the woman she raised me to be.

[00:07:42] I didn't know how to do that. I mean, that's the hardest thing when you're at your low moment to say, "How do I change? How do I go forward? How do I be different?" But I knew that if I did something that was hard and I mean, physically hard. If I did something that was solitary, that required me only to depend on myself that I would feel more whole. And of course, if I did it in nature, I knew that nature always made me feel that sense of wholeness. You know I sort of was casting around for, in a vague kind of way for this thing to get me back to myself. And I came upon, I happened to be in an REI store outside of Minneapolis. I was living in Minneapolis at the time. And I came upon this book, this guide book, I was waiting in line. I was buying a shovel, which ends up — you know, it's totally a metaphor. I had to dig myself out. It's funny how life could be a metaphor. And I came upon this guidebook. I'd never heard of the Pacific Crest Trail. And there was this book I thought, "Wow, there is this long national trail that goes from the Mexican border to Canada, through California, Oregon, and Washington. What would it be like to walk on it?" And so that's where it began. I just decided that I would be expanded by doing this thing. 

Jordan Harbinger: [00:09:02] So heroin being a cure for the pain, the same reason you hiked. It seems slightly healthier to hike versus doing heroin, I guess. So there's that. You've been through the other side. I wonder when you see people who are like in the streets, you know, these homeless people or just people who are on drugs, do you have a different feeling of empathy for them than maybe a lot of other people do because you also were — maybe not on the street doing it, but a few steps away, probably? 

Cheryl Strayed: [00:09:32] Absolutely. I mean, everything I've ever done, every experience I've ever had, positive and negative, it's given me a deeper understanding of whatever group of people that is. When I used drugs, when I used heroin in particular, I saw how powerful that feeling is to want to do it again, and again, and again. How also awful that feeling is, I mean, it wasn't like when I was using heroin, I was thinking, "This is a blast. This is wonderful." What I was thinking is what am I doing, what am I doing? This isn't what I was born to do and be. And yet there was such a strong pull. And I will say when I do see addicts and I have met a lot of addicts and the years that I've been talking about Wild and I work — you know, a lot of people, thankfully in recovery, there is I think, nothing more humbling than seeing firsthand, how you can slip, how you can lose your life to the disease of addiction.

[00:10:31] You know, I never became a heroin addict. I used it destructively but I danced along the edge of that danger. And thankfully I had people who I loved and who loved me intervene and pulled me out. And I also had just enough presence of mind to say the right, "I can't do this." And so, you know, I didn't go all the way into addiction, but certainly, I have that sense of humility and compassion for people who, who have lost their lives to it, or certainly many years of their lives. You know what I always think when I do see addicts who live on the streets or who are struggling in their active addictions, is that there's always the possibility of change. That every day is a day that you can step toward recovery. And I always sort of send a little prayer to those people.

Jordan Harbinger: [00:11:20] This is maybe a little — is it inappropriate? I don't know. What does heroin feel like? Because if anyone can describe it in words, it's probably you. 

Cheryl Strayed: [00:11:29] Well, the unfortunate thing is heroin feels really good. Good physically. There's like an ecstasy kind of feeling, but I think more powerfully and more importantly and the thing that I was so struck by the first time I used heroin is how it took away, at least temporarily, my emotional pain. And I wrote about this in Wild. One of the things — I mean, it was really like one of the biggest surprises of my life to have the feeling that I wasn't any more suffering. I knew my mom was dead but I wasn't grieving her when I was high. And of course, this is the story in a time of my life where every day was hard to live without my mom. I woke up and I was sad, really sad, really in pain. You know like I said, I'd lost my family. I'd lost my mom. I had lost my marriage. I was married to somebody I loved and I divorced him because I couldn't sustain that bond in the wake of my mom's death.

[00:12:29] So there was a lot of sadness in my life. And when I used heroin, it felt like, "Oh, this is the thing that makes it okay for me. This is the thing that allows me to live." And so like a savior, which is a terrible thing to say. And you asked about my, the insights I gained by using really that in a huge way. Like, I just think, wow, you know, the reason that so many people turn to drugs — and that I also quit alcohol. I drink but I don't suffer with alcoholism but you know, the people who do turn to drugs, in ways that we see as destructive, very often they have turned to them out of a sense of pain, a sense that they're seeking some way to ease their pain.

Jordan Harbinger: [00:13:14] It's tragic when you think about it like that. And when you see — I mean, heroin sounds like a very dark teacher. I assume you also see it that way, right? I mean, it's — 

Cheryl Strayed: [00:13:24] Oh, absolutely. And there's no upside to using heroin. I mean, the other thing, Jordan, I want to say is I'm 51. I was really in the whole kind of grunge, Nirvana, you know, '90s generation. I was in my 20s in the '90s. And there was such a sort of rocker chic. I would have never admitted this in my 20s when I used heroin that I did it because I thought it was cool. But now. I'm like, oh, yeah, of course. You know, there was this incredibly powerful idea, especially now it's important to again, it's like, yeah, the cool people are using heroin. That's what the cool people in the scenes, to like the sort of some of the circles I moved on. It was a very common thing. And you were part of the cool club if you used it. And so that's another aspect of it. You know, there was the suffering on top of just my need to feel accepted and welcomed by people, I guess, I looked up to.

Jordan Harbinger: [00:14:24] That's scary that it can start as like this is trendy and then —

Cheryl Strayed: [00:14:27] Yeah.

Cheryl Strayed: [00:14:27] It really is almost like a '90 PSA drug commercial, and everyone's like, "Whatever, you're not going to find — that's not a thing that's going to happen." It's like, "Oh, no, try this. It's cool." 

Cheryl Strayed: [00:14:36] Yeah.

Jordan Harbinger: [00:14:37] Heroin, like that should be kind of like outside the whole, "Hey man, give this a shot. It's cool. Everyone's doing it," right? 

Cheryl Strayed: [00:14:42] Yeah, totally. 

Jordan Harbinger: [00:14:43] And when you started the hike, you couldn't even lift your pack. That's a problem for an 1,100-mile trek, generally. 

Cheryl Strayed: [00:14:51] It's really a problem. It's so much a problem. You know I couldn't lift it because I made the very common novice backpacker mistake of taking too much stuff. And as you mentioned before — so let's just first this out of the way. I had never gone backpacking before I went and hiked 1,100 miles of the Pacific Crest Trail, okay. I had hiked a lot. I had grown up in the wilderness, so this was not — it wasn't as if I just, you know, was this like a thin sock city girl, who'd never gone out into the woods. I did grow up in Northern Minnesota without electricity or running water or indoor plumbing for a good part of my teenage years.

Jordan Harbinger: [00:15:28] Wow.

Cheryl Strayed: [00:15:28] Yeah. So I had experienced, I loved the wilderness and I also had gone on lots of day hikes. I loved to hike. But what I learned when I packed my pack is backpacking is different than day hiking. So you have to carry everything. And I could not lift my pack on that first morning of my hike. I had to lift it and get out the door to go to the trail. 

Jordan Harbinger: [00:15:52] So how did you do — did you just kind of like do some gymnastics and get it to rest on your shoulders? I mean, how did you even manage to get out the door?

Cheryl Strayed: [00:16:00] Well, you know, one of the great things of having a movie made of your book is you actually get to say, "Yeah, watch the movie. That's how I did it." Basically, I wrestled with my pack. It was really this moment of truth and that I had checked into a motel in the town of Mojave, California the night before I began my hike. And this moment of truth was about like, I've got to go. I can't lift this pack, but I have to lift this pack.

[00:16:25] And, you know, years later I saw that for the metaphor that it is. I saw that really the thing I was writing about when I was writing Wild is this question of not just how do I hike this trail? How do I grieve my losses and move forward? But how do we do it? How do we bear what we cannot bear?

[00:16:43] Of course that first day in the motel room when I had to bear what I could not bear, I didn't know the answer to that. I only knew that I had to. It was like an epic kind of paradox. Like I have to do the thing I cannot do. It's present and not like every fairytale tale throughout time. Our protagonist must do what does it mean possible?

[00:17:04] And what I did is I just got that dang pack on my back. I wrestled it. I sat on the floor and strapped it around my shoulders and rocked myself forward and threw myself forward into my hands and knees. And then I did a squat. Like my legs are stronger than the rest of me, so I just squatted up and I couldn't stand up straight beneath it, but — 

Jordan Harbinger: [00:17:25] Wow.

Cheryl Strayed: [00:17:25] I walked out the door. You know, in Wild, I called it, I was hunching in a remotely upright position, but that's the beauty, I think of any kind of recovery, I guess. It's you don't have to be doing it perfect. You don't have to be upright. You don't have to be fast. You just have to get yourself in a remotely upright position and go. 

Jordan Harbinger: [00:17:42] it was nice of your backpack to have this built-in metaphor for the book. Like we're bearing the weight we cannot bear. And it's like, no, it was just really heavy. 

Cheryl Strayed: [00:17:51] Well, I mean, that's it. It's like that's the trick of writing a memoir honestly. You know, so many people kind of misunderstand the form because I think like all you need is to have some exciting or terrible thing happen to you and there's your book. That's not true. I mean, we all have the exciting and terrible things happen to us. What you have to do is try to mine your life for its larger meaning. I wasn't interested in writing a book that was just about my grief or my hike. You know, I really was looking for, what is the human story here? That's what memoirs do is they simply use the self to tell the human story.

[00:18:24] And yeah, once I started, once I realized, "Oh, okay. Yeah. I have something to say here about this journey," it was so metaphorical that I actually had to sort of tamp it down. I had to be like — even, you know, things like later as I'm hiking on the trail, I nicknamed my backpack Monster because it was so big and heavy and it was like my companion. And later when — you know, that was something that I wasn't thinking like, "It's a metaphor. I'm carrying my own monster on my back." But later when I read the book, I'm like, "Wow, it's a monster." And we all have to learn to make friends with our monsters. 

Jordan Harbinger: [00:18:58] You can't get away from yourself when you're hiking. You know, I was a Boy Scout for a long time. I did hikes. And like, it's kind of — like, you know, when you're in the shower and you have thoughts and you go, "Oh, that's a good idea." Or, "Ooh, I shouldn't have done that." "Hey, I wonder if that person's still mad at me." Hiking is like a multi-day shower where you're just thinking, and you can be ruminating or you can be having positive thoughts and you can also, at least — maybe I should speak for myself. I can get really sick of my own company. Did you ever get sick of yourself? 

Cheryl Strayed: [00:19:28] Oh, my gosh. All the time. That, I think, is the most challenging thing of long-distance hiking and especially when you do it alone, like I did. You know, there it's glorious and beautiful and it's all these things, but it's also extremely monotonous. And what happens is your mind needs a story, your mind needs entertainment. So I found myself thinking about everything, literally, like everything in my life, which is in so many ways what made the hike so healing really, because I had to think through all of the different experiences and relationships and they were just there.

[00:20:02] And the other thing is, I will say too, I didn't realize when I was writing Wild, that I was in some ways writing about the way the world used to be because I took my hike in 1995 and this was before most of us were on the Internet. A couple of people were learning what the Internet was by then, but most people were not. This was before cell phones. So I was really alone out there. This was also — you know, even music. I missed music more than anything. I would sing songs to myself in my head. I didn't bring the sort of mobile music available at that time. There were these things — you must remember a Walkman.

Jordan Harbinger: [00:20:39] Oh, yeah, so you had cassette tapes. Oh, my goodness.

Cheryl Strayed: [00:20:42] But I didn't take it with me because, of course, I'm not going to carry a Walkman and batteries and cassette tapes. Now, on the trail, people have their phones and their music. I mean, you can listen to audiobooks. I mean, people do all kinds of things now when they're hiking. I had no technology. There wasn't technology. It was just me and my mind. And I feel lucky, honestly, that I hiked the trail in that era -- in that era when we could still be alone. 

Jordan Harbinger: [00:21:13] Yeah, that's an interesting point. I know you did run into some — like one guy had an early cell phone on the trail. 

Cheryl Strayed: [00:21:20] Yeah. I mean, that was the first time I learned about this concept of a cell phone. One of the men I met — he's one of the Eagle Scouts I wrote about him in Wild. He had been asked to carry — it was like this big plastic block with numbered buttons on the front. And I was like, "What's that?" And he said, "It's this thing called a cell phone. And they want me to turn it on to see if it will work out in the wilderness." I just distinctly remember I was standing with two other hikers when he told us about it. And I just distinctly remember the consensus was, "This was the most ridiculous idea that we had ever heard of to ask people to actually carry phones around with them." And what's so funny about that is, of course, now like we're all just constantly — if I'm ever like a foot away from my phone, you know, that's kind of surprising, right? We always have our phones on us. But when I first heard of it, it just seemed like such a bad idea. It seemed like nobody would agree to do that. I mean, that was always one of the pleasures of just having a landline is you were either there or you weren't, and if you couldn't be reached, you couldn't be reached. We don't live in that world anymore. 

Jordan Harbinger: [00:22:22] Yeah, it was like — yeah, we do not. I was going to say, I wish you'd been right about — like, "This product, this is never going to take off. No one is going to want one of these things." And here we are. 

Cheryl Strayed: [00:22:32] Totally. I know, I know. Clearly, there's a reason I'm not in like you know — 

Jordan Harbinger: [00:22:36] Adventure investing?

Cheryl Strayed: [00:22:37] Development.

Jordan Harbinger: [00:22:37] Yeah, you're a regular technology oracle, Cheryl, yeah.

Cheryl Strayed: [00:22:40] That's right. That's right. I thought it was a very bad idea.

Jordan Harbinger: [00:22:44] A website with all of our personality profiles on it. Ugh, nobody's going to want that. What would that be like a Facebook on the Internet, yucky?

Cheryl Strayed: [00:22:51] That's right.

Jordan Harbinger: [00:22:52] I think a lot of people wish you were kind of right about that, although yeah, whatever, that's a whole different show, like what tech does for us and what it doesn't. But it does seem a little bit like a wasted opportunity to have. Instagram and podcasts and audiobooks at your beck and call all the time. Although then it's just an exercise in discipline and not just like checking in with your friends and having Zoom calls from the trail, you know, all the time.

Cheryl Strayed: [00:23:13] Yeah. I mean, it's a complicated thing. I mean, people often ask me about this because, of course, when I say, "Oh, I feel so lucky that I was really out there alone." And by that too, I mean, you know, the connections to friends, as you say, like you can connect to people from the trail. Now, you can FaceTime with them. You can text them. So in that way, you're not really — you're alone but also not really in that way that I was. Like, I was actually alone. The only way to contact me when I was on the trail was either to walk up to me and be there in person or to write me a letter at some post office that I might come to and collect my mail at some unknown date in the future.

[00:23:48] And that's a profound experience to really be alone, to really be disconnected from anyone you know or love or can depend on. And I treasure that experience and yet, like, I totally get it. Like when I hike now, yeah. I have my cell phone in my back pocket. Like I understand why they don't disconnect. It's so hard to do. And I am not an anti-cell phone or Internet. I do think that it's powerfully connected us in ways that are really important. And yet it's complicated. Isn't it? Like, how do we go back in time and find that kind of solitude again? I think it's a loss if we don't.

Jordan Harbinger: [00:24:25] You're listening to The Jordan Harbinger Show with our guest Cheryl Strayed. We'll be right back.

[00:24:30] This episode is sponsored in part by DesignCrowd. There are plenty of reasons you might need to hire the services of a designer. Perhaps you need a logo for your business, a little personalized stationery. It could be nice to include infographics on your podcast show notes, you never know. But DesignCrowd can do better than finding you one measly designer to suit your purposes. You can find over half a million from all around the planet. Here's how it works. Go to designcrowd.com/jordan. That's D-E-S-I-G-N-C-R-O-W-D.com/jordan. DesignCrowd invites 750,000 designers to respond to your request. You get dozens, even a hundred or more designs from different designers around the world within about a week. You pick the one you like best and you approve payment to the winning designer. If you don't like any money, back-guarantee. That's what we expect these days. Whatever your purpose, just about any creative project can be crowdsourced on DesignCrowd. Holiday cards, stickers to proclaim your latest clever shower thought from every car bumper in the land, the possibilities are limitless. Jen, tell him where to check out this deal. 

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Jordan Harbinger: [00:27:25] And now back to Cheryl Strayed on The Jordan Harbinger Show.

[00:27:31] What was the longest stretch that you went without seeing anyone. You know, you had to have some of those, right? 

Cheryl Strayed: [00:27:37] Yeah. And right off the bat. I mean, that was the hardest thing. The first eight days of my hike I did not see another soul which was astonishing to me. I mean, I think most people don't go eight days without ever seeing anyone. You know?

Jordan Harbinger: [00:27:50] No.

Cheryl Strayed: [00:27:51] I mean, obviously, so many people during the pandemic are held up in their houses and maybe not seeing others, you know, in person, but we're still connected. So when I say eight days of not seeing another person, also just not communicating with anyone in any way, it was really deep. And it was very common too after that, to go three, four, or five days without seeing people. I was so surprised by how remote the trail was. I knew it would be solitary, but I didn't know it would be so solitary. 

Jordan Harbinger: [00:28:21] I mean, no electronics, no phones, no iPods, no drugs, no booze, no escape from your escape that you're trying to make there. And I mean, I get scared of going into my childhood home's basement and you left civilization entirely which is — 

Cheryl Strayed: [00:28:34] I love it. I love it. That makes me happy. Yeah. Yeah. I have to say even — like, I know I'm glad I did it. And even when I now hike alone sometimes, like I still sometimes get a little creeped out feeling. I remember how fiercely I had to tell myself back then that I wasn't afraid. That was my mantra. I am not afraid. I am not afraid. I am not afraid. And of course, I said it because I was, and I was having to tell myself that I had to be brave and strong in order to do this thing that I really wanted to do. And of course, that lesson has paid off a lot over time. It's something that I've drawn on again and again. 

Jordan Harbinger: [00:29:14] When were you most afraid? Because there are animals and stuff. Or did you just get used to it?

Cheryl Strayed: [00:29:18] Yeah. Well, you know, first of all, I want to say it's funny our idea about what is dangerous is really off-kilter. One of the questions I get so often is about this idea of like, "Weren't you afraid? Weren't you afraid?" And it's like, well, you know, statistically, it was so much more dangerous for me to stay in civilization, in the city that summer — 

Jordan Harbinger: [00:29:38] Oh, yeah.

Cheryl Strayed: [00:29:38] Then it would have been, you know — and obviously drugs, you know, that's dangerous. I was doing dangerous stuff. But even things like you're much, much, much more likely to die in a car accident than you are hiking on a trail in the wilderness. But because we do that so much, we normalize it. So yes, having said that, I was afraid of snakes. I was afraid of bears and I was afraid of cougars, otherwise known as mountain lions. And you know, those are real things and I encountered bears and snakes several times. I probably encountered mountain lions, but I didn't see them. I'm quite sure they saw me.

Jordan Harbinger: [00:30:14] Yeah.

Cheryl Strayed: [00:30:16] You know, I was walking through cougar country for sure. You know, I was also afraid of men. 

Jordan Harbinger: [00:30:22] Yeah, that's a good point, right? Because a cougar might go, "Ah, she's too big," but a drunk guy might not make that same calculation.

Cheryl Strayed: [00:30:32] Yeah. I mean the human animal who's the most dangerous one to women is the human male. And I was first leery — you know when I first started, most of the people I met on the trail were men. And I pretty quickly saw that like one of the coolest things about long-distance hiking is you tend to meet really good people out there on the trail. It's an endeavor that draws people, I think, who have good reasons to be out there.

[00:31:01] And even though we might have all kinds of differences, we're both doing the same thing. It's difficult, It's beautiful. It's magnificent. It's all those things that we shared that bond. And so I really, you know, very quickly realized that I was meeting amazing men out there and I didn't feel threatened by them.

[00:31:19] I did finally well into my hike once I had sort of grown quite at ease about being on the trail. I did meet two hunters in Oregon, and that was a really scary experience because it was the first time that I met people who were menacing to me. And I really, honestly, thought I was going to be sexually assaulted. I wasn't, but I felt like I came really close, and I was scared enough that as finally when they left, I packed up my things, and even though it was night, I ran. I didn't dare stay camped where I was camped because I was afraid. I was afraid. 

Jordan Harbinger: [00:31:58] Yeah, that's terrifying, especially with there's just nothing around, right? Ugh, gosh.

Cheryl Strayed: [00:32:03] No. And you know what? It's such a difficult experience because of course, I felt so empowered by the trail and really in so many ways kind of revising a story that women are told about like, "Don't go alone. You need a man to protect you." And I got into this place where I just felt so strong and like I could protect myself. And what those men did in sort of being menacing to me and talking to me about my body and saying things to me that made me feel really afraid and uncomfortable is that they sort of reminded me that they had that kind of power. And really the fact that I wasn't sexually assaulted, I feel like it was luck. It's a sad reality for women travelers around the world, whether you are on a hiking trail or elsewhere. And you know in some ways, I was humbled by it. And it was a corrective to a kind of confidence that I had out there. And yet it didn't, in any way, take away that sense of agency that I had when it came to making that hike happened for me. 

Jordan Harbinger: [00:33:06] Did you ever come close to running out of food or water or is that not really a concern? 

Cheryl Strayed: [00:33:11] Oh, yeah, yeah. No, it's a big concern, especially running out of water. I did — 

Jordan Harbinger: [00:33:15] Yeah, that will really kill you.

Cheryl Strayed: [00:33:16] Yeah.

Jordan Harbinger: [00:33:18] And quickly.

Cheryl Strayed: [00:33:18] Food is miserable to run out of it because you're like, okay — and that was always it because you carry food and you carry food for a set number of days. You calculate that. I'll be at my next stop in nine days, so I need nine dinners and nine breakfast — you know, that kind of thing. So if something happens that slows you down, you can run out of food in that way. Water is the bigger deal because also here again, now when you hike a long trail, there's all this information that you can access online. Like, "Oh, that Creek is dry," or "This source is available or not available." 

[00:33:52] So for me, back in 95, it was just kind of a word on the trail. And I was walking across this very hot section of the trail in Northern California called the Hat Creek Rim. And I was told there's this kind of big tank kind of midway through that these ranchers have for their cattle and it was a water source. It's a water source for hikers. And I knew that I could only carry a certain number — a lot of water to get to that tank and I was told there was water in that tank. And I got there and the tank was empty and I had no water and it was like a hundred and some degrees. It was incredibly hot. Really that's the most dangerous day, I think, I had on the trail because I was miles from the next water. And so I had to walk as quickly as I could through the heat without any water. And I knew that I was putting myself at risk, but there was nothing I could do.

[00:34:44] So I finally came upon this really muddy, awful, dingy pond. And I pumped water from it. It was brown. It was like brown water, drinking, mud water, but I was so grateful for it. It was like the hottest tea, you know, that kind of water in the summertime. It was miserable, but it was water and it saved me. 

Jordan Harbinger: [00:35:05] That's really gross, but I can totally — it probably also was almost like the worst yet best water you've ever tasted in your life in some way.

Cheryl Strayed: [00:35:12] Yeah. And I pumped it — you know, I had a water pump. I also had iodine pills and I both pumped the water and put iodine pills and to double treat it, but it was still like really wretched brown water that then tasted like iodine. 

Jordan Harbinger: [00:35:28] Yeah. Better than dying though. Definitely better than dying.

Cheryl Strayed: [00:35:30] Yeah. Better than dying.

Jordan Harbinger: [00:35:32] There are a few things in the book that are like, well, better than dying. I mean, there's a lot of lost toenails and I think for anyone who's never had a toenail sort of coming loose that you then have to pull off. I don't necessarily wish that on anyone, but it's quite the experience, especially when you put your dirty, wet, sweaty socks back on and you just keep walking.

Cheryl Strayed: [00:35:49] Yeah. Have you ever lost a toenail, Jordan? 

Jordan Harbinger: [00:35:52] Oh, yeah. Yeah, yeah, It's gross.

Cheryl Strayed: [00:35:53] It hurts.

Jordan Harbinger: [00:35:54] Especially during a hike and it's like loose. And you just go, I can't have a loose toenail, so you either taped it on as tight as you can, but sometimes that just makes it worse and it's just like squishing around. So there's that moment where you just sort of like grit your teeth and just grab a hold of it. And then like grab a hold of, I don't know, like another object to squeeze on it and you just pull it off and it's like the grossest squishy sound. And then you flick it into the woods and you just like to put a Band-Aid on it. If you have one and keep on marching, 

Cheryl Strayed: [00:36:25] It's so gross. I lost like six toenails over the course of my hike — 

Jordan Harbinger: [00:36:29] That’s a lot.

Cheryl Strayed: [00:36:29] — but I lost both of my big toenails.

Jordan Harbinger: [00:36:31] Ooh.

Cheryl Strayed: [00:36:33] Really, the most painful part was like, before I realized, like, okay, I have to like rip them off because my toes swelled up. It's basically my toenails popped off because those big toes swelled so big that it forced the nail off. It sounds so gross, but it was so painful. And then the nail was still like pressing down on the swelling. Once I pulled it off, as much as it hurts — like you said it hurts to pull it up — there was at least some relief because it was like, ugh, you know, it wasn't impinging my swelling anymore.

Jordan Harbinger: [00:37:05] Right, yeah.

Cheryl Strayed: [00:37:05] We're really getting into it here. 

Jordan Harbinger: [00:37:06] We're really selling the hiking idea, I think, to them.

Cheryl Strayed: [00:37:08] We are. We are. Yeah. And basically what happened is it was like because PCT, like lots of trails, it's a lot of up and down. Like you're walking through the mountains. And when I would descend it would be like that my toes would just slide forward in my boots, no matter how I tied my shoes, no matter what I did and those toenails, which has to be battered and destroyed 

Jordan Harbinger: [00:37:31] Hiking has a lot more ups and downs. I think we're just sort of focusing on some of those. Maybe we can switch it to like some of the benefits because right now, everyone's like, why would anyone don't ever do this? You've said that life's hardest moments are what make us who we are. And I definitely agree with this. I'd love to hear why you say this because, well, it's true, but it's also one of those semi-cliches that usually when people say this, they never explained why.

[00:37:53] So someone going through a hard time often can't really get comfort in that, especially if they're like me and they want to know why, why, why, why, why. It's like, "Oh, life's hardest moments." And they're like, "Yeah, but that's right now for me. And that I don't feel like I'm growing," you know? 

Cheryl Strayed: [00:38:07] Yeah. I mean, I think really we are required to trust the fact that very often, we can't feel in the moment what will be in the end the truest thing when we are going through a hard time, whether it be a hard time emotionally or a hard thing, physically slogging up that hill or running that marathon or any of those things. What you're thinking is, "I want out of this. Why did I do this? I wish this weren't happening to me. This is hard! It's not fun." You know, that's what it feels like right in the moment. What it almost always feels like afterward is, "Wow, I did that. I'm stronger than I was before. This taught me something that is going to be powerfully important to me for the rest of my life." Or, "As much as I wish that hadn't happened, look at the changes that I've made, the things I can see now, and know now that I couldn't have and wouldn't have known before."

[00:38:59] You know, I think of hiking often as retrospective fun. I think running is this way too. Like very often as we're doing those activities, we're not like, "Yee-haw, this is the best thing." You know, sometimes we are, but sometimes we're like, "Ugh, I cannot wait to get to the trailhead or the mountain top," or whatever it is. But we're always glad we do it. I call it retrospective fun. You look back and go, "That was a blast."

[00:39:21] And I think that with our emotional struggles, it's a little different. We don't look back and go, "That was kind of fun to actually have to get divorced or lose somebody I love or break up," or whatever that is. But very often, almost always we look back and say, "It was worth it. I do not regret it. I am stronger and better for it." And so, you know, I think we just have to trust that. I try to trust that in my own life and even if you can't get all the way there. Like I think it's incredibly hard — like I said, my mom died at 45, it's incredibly hard for me to spin that into a good story. I think that it's really awful that my mom died when she was 45. And yet what I can say, the gifts I received because of the love I have for her and the things I learned about what it means to love someone after they're gone are really important and powerful. And they are the things that in so many ways have made me who I am.

[00:40:22] And, you know, two things can be true at once. You can look back at something and say, "I wish it hadn't been that way." You can also say, "But because it is, I'm better for it."

Jordan Harbinger: [00:40:32] You had an interesting experience with your mom before she passed, which no one has actually, you went to college together and I think that's — how did that happen? That's so unusual. I don't know anyone else that's had this experience. 

Cheryl Strayed: [00:40:44] Yeah. Very few people would sign up for this experience, Jordan. It's not a popular choice to bring your mom to college. So here's what happened. I grew up in rural Northern Minnesota, 20 miles from a tiny town called McGregor, Minnesota in rural Aitkin County. And I wasn't in this orbit of like college-educated people or, you know, nobody was saying to me, "Where do you want to go to college?" or taking me on college tours. Nope. I didn't know anything about how to apply for college. And nobody around me did either. I started to receive brochures in the mail as you used to get when you were in junior and senior. And it was my understanding that I would just sort of study those brochures and pick a college based on that. I didn't know I was supposed to apply to more than one college. I applied to one. It's the University of St. Thomas, which is this Catholic private college in Saint Paul, Minnesota. And I applied there.

[00:41:34] And when I got the acceptance letter — thank goodness, they accepted me. In the letter to sort of try to persuade me to go there, they said one of the benefits of being a student here is your parents can attend college for free. So what they were thinking is they were thinking like somebody's mom or dad would take like French 101. You know, like there would be some little thing like that. And my mom was at the time 40 and I read this letter to her and she said, "I have always wanted to go to college," which I knew was true. And I knew that my mom had not gone to college really because she was my mom. My mom got pregnant when she was 19, she married my dad because of that. She had three little kids by the time she was 25, 26. She had really had to sacrifice so much to raise us.

[00:42:22] And my first thought was like, "Okay, you are absolutely not going to college with me. Forget it." But what happened is I knew even in the height of my kind of youthful arrogance — my teenage, you know, like I got to get away from this woman — is that it was a wonderful opportunity and I didn't want to stand in the way of it. That my mom deserved to go to college.

Jordan Harbinger: [00:42:47] Yeah.

Cheryl Strayed: [0042:48] Even though we both were like, "Well, she's probably not smart enough. She'll probably flunk her classes." It wasn't like, we were like, "Yeah, my mom is so smart. She should go to college." So we decided that she could go. I would go live on campus in the dorms. She would commute. It's three hours away from the house where I grew up. We had one rule and that was she couldn't speak to me or acknowledge me. If she saw me on campus, she was not to address me. Because I was just like, "Mom, back off." She was like, "Okay." And now, of course, I laugh about that, but you know, I was 17. I went to college when I was 17 and I was doing what I needed to do. I needed to separate from my mom. And of course, what happened is she went and she was just like, "Wow. My world opened up." Her world opened up. She got straight A's. All of her professors loved her. She thrived. 

[00:43:36] So you know when she died — I just went to Saint Thomas that first year. I was paying for my own college and I realized, "Oh, private tuition was way too expensive." So I transferred to the University of Minnesota. And so did she, she went to Duluth, which was closer to our house. And I went to Minneapolis. We were about to graduate. She actually died over the spring break of our senior year of college.

Jordan Harbinger: [00:43:57] Oh, man.

Cheryl Strayed: [00:43:01] She was two classes shy of her degree. She died and the college granted her degree posthumously.

Jordan Harbinger: [00:44:05] That's amazing. I mean, it just seems so close. Right? So close to that. 

Cheryl Strayed: [00:44:09] Yeah. It was such a heartbreak. It was such an unbelievable heartbreak. 

Jordan Harbinger: [00:44:15] You always asked really inappropriate questions as a kid. Is that right? 

Cheryl Strayed: [00:44:19] That's right.

Jordan Harbinger: [00:44:20] So I love that.

Cheryl Strayed: [00:44:21] I'm sure you do. 

Jordan Harbinger: [00:44:22] Yeah. I mean, that's kind of like what I try — I wish my job was to ask like, just the most ridiculous, but I have to ease into it because I'm a grown man here. So there's an element there that I can't get away — like I can't be like, "When did you lose your virginity? Oh, sorry. How do you spell your last name?" Like, I can't really get away with that, you know, 

Cheryl Strayed: [00:44:37] I always ask people about their virginity.

Jordan Harbinger: [00:44:39] Really?

Cheryl Strayed: [00:44:40] They don't always appreciate it. Yeah.

Jordan Harbinger: [00:44:41] That's funny. Why that specifically? 

Cheryl Strayed: [00:44:44] That's the thing. Like, I've always been most interested in people's personal, private, emotional lives. And I've always wanted to know. Like, what's really happened in people's lives. I'm not interested in the kind of veneer or the face they show the world. I've always been interested in what you really think or feel? Or why did you do this and when? I think that asking people about when they lost their virginity is a really pretty deep question because almost always like, if you really go beyond the kind of like, "I was 17 and it was in, you know, blah-bitty-blah." If you go beyond, if you ask for the story behind that you almost always hear something really interesting about life.

[00:45:28] And I think it's interesting and sad that you know, obviously, we have to function the world. We can't all go around constantly telling our darkest secrets and yet that's to me, what really ultimately connects us to each other. That when we really see the person behind that facade is when we actually find — that we are connected to them, that we have things in common with them. That we're curious about another life. And so, yeah, I've always wanted to go there since I was just a child. Yeah. 

Jordan Harbinger: [00:45:57] The most popular episodes of this particular podcast are what we call Feedback Friday, where we give advice to listeners that write in about anything from "I'm new at work," and, "I want a raise," or other people are like, "My parents are both cheating on each other. Like what do I do?" You know, we have all kinds of crazy stuff like that. I know you were Dear Sugar for years and years.

Cheryl Strayed: [00:46:16] Yeah.

Jordan Harbinger: [00:46:17] What are your rules when you give advice to people? Do you have any kind of things that you're keeping in mind or particular guidelines for yourself? 

Cheryl Strayed: [00:46:24] You know, I'm not writing a column or I don't have the podcast active right now, but I think I'll be Sugar forever. Dear Sugar just took the job on, it was an unpaid job. So to call it a job as a stretch.

Jordan Harbinger: [00:46:34] Yeah, it's a stretch, right?

Cheryl Strayed: [00:46:35] I started writing the column for the Rumpus website. And I thought it would just be a kind of lark. Like, oh, my gosh, you know, all my life I've wanted to know people's secrets. And finally, I get them in this form as this advice columnist, but it pretty quickly became really, I think, a very serious endeavor for me. And I think the writing that I collected the columns in my book, Tiny Beautiful Things. And I think it's really some of the most powerful and important work I've ever done. And it was because, of course, I was trying to give people advice, the person who wrote to me. But again, like I was trying to kind of mind that struggle or that conundrum. And illuminate like, what is it? Who are we? What does it mean to be human? You know, I always wanted to kind of delve beneath the questions that were asked.

[00:47:17] So your question, what do I think about when I give advice? You know, I think that advice has been misunderstood in a lot of ways. Like they think like, you know, I seek your opinion. And very often the worst advice comes from somebody who's rooted only in their own story who's like, "Here's what I think everyone should be like." And what I try to do when I give advice is to really listen very hard to what the person is saying to me about themselves. Very often, if you listen hard, what you can see is that the person knows what they want. They know what they need to do. They just need somebody to tell them it's okay to do it. 

Jordan Harbinger: [00:47:52] Yeah. A lot of it is permission. I've made that mistake a lot. People will say, "Do you have any tips on me starting a clothing business?" And I'm like, "Well, you know if I were you, I would go work for a clothing business and get used to supply chain because that's always the biggest problem. And don't worry about the design stuff yet. You know you can worry about that later. That's just the fun part. You need to get experience at all levels of the business." And they're like, "This sucks. This advice sucks." What they want is for me to say, "You know what, go for it, give it a shot. And if you fail, it doesn't matter. You're young. This is going to be a great experience for you." That's what they really want to hear. And I'm just like in dad mode telling them how to set up their LLC or whatever, you know, like all and their supply chain. And they're just like, "You're a dork Jordan, you know, I don't want to hear this."

Cheryl Strayed: [00:48:34] Yeah, you know, I think that's really true. And also think about this. Like, you wouldn't have wanted to do everything right from the beginning, right?

Jordan Harbinger: [00:48:42] No. I think I still don't.

Cheryl Strayed: [00:48:43] Because you learn from your mistakes. I mean, people often ask me like, "Well, knowing what you know now would you have packed less in your backpack?" And I'm always like, "No." You know, of course, my advice to backpackers would be like pack light because it's hard to carry a heavy pack. And yet I myself would not want to go back in time and carry a light pack. Because we never forget the lessons we learned the hard way. And so that is a complicated thing. Like there's no one path to the mountain top. The way to do it right is to do some things wrong. Most of us here — this goes back to that question you asked me about like the hard things. It's like, yeah, most of us actually found the best things in our lives after having failed a bit, made some mistakes, or done some regrettable things. 

Jordan Harbinger: [00:49:28] This is The Jordan Harbinger Show with our guest Cheryl Strayed. We'll be right back.

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[00:52:21] There's something called Solomon's paradox. I think that's what it's called. And it's we give better advice to others than we would ever give to ourselves, right?

Cheryl Strayed: [00:52:27] Oh, for sure.

Jordan Harbinger: [00:52:28] Because when we talk to ourselves — I think this is why we do it, anyway. When we talk to ourselves, we weigh everything. We're like taking into consideration our emotions and how we feel in the moment. And like all of these factors that may or may not have anything to do with anything. But with others, we never have enough information, right? So we focus on what we can see, which are often the more obvious factors. And there's no emotion in it. Because I don't care if your business, like I don't want your business to fail, but I don't really — I'm not going to cry and be broke and have to call my mom and admit I was wrong if your business fails. That's you. You have to do that.

Cheryl Strayed: [00:52:56] Yeah.

Jordan Harbinger: [00:52:57] But that can make advice better as long as it's tactical. Like when I was a lawyer, I was giving advice that theoretically I was technically qualified to give, I was obviously supervised in the beginning. But it's hard to give advice that you yourself would follow. I find that it is anyway. I don't know about you.

Cheryl Strayed: [00:53:12] Yeah. And I think too, for me, the nuance about that is that also when I'm giving advice, I'm speaking to the best version of myself and the best version. I think the other person can be. Like, if somebody asked me writing advice, I say things like, "You just have to trust the process and you have to keep going, even when it's hard and you have to believe in yourself," and like, you know, I say all of those things, well, every day, every day I myself have to struggle with those very things. It's not like I have landed on some kind of island where it's like, "I'm just always floating past in my little sort of best-self raft."

[00:53:52] And so advice is about aspiration in a lot of ways. And of course, the advice-givers, I think, are almost always the best-advice givers when they themselves are also wrestling with those questions. And it's nothing, nothing is really static. I mean, obviously, legal advice is a different kind of thing where it's like, you should do this or something. But I think that kind of nittier-grittier advice you're talking about like — you know, today is my 21st wedding anniversary, by the way.

Jordan Harbinger: [00:54:16] Oh.

Cheryl Strayed: [00:54:16] Happy anniversary — 

Jordan Harbinger: [00:54:17] Congratulations.

Cheryl Strayed: [00:54:18] — to me. And you know, people are like, "Well, how do you stay married for 21 years?" And it's like, "Well, you know, there's a whole bunch of different ways and you could do them all and then your marriage could fail." I mean, like there's no one prescription, it's always an active effort, I think. Luck plays a role too. You know, I don't want to attribute everything to that but I think sometimes you just — you know, you started the business time or you signed the wrong contract or you married somebody who then changed their mind 15 years down the road and you couldn't have possibly seen that. You have to trust I think that advice is always as good as what you can possibly manage to do and follow and believe that day.

Jordan Harbinger: [00:54:56] "Writing forces you to confront demons," you said. And I wonder if we all have these sort of negative voices inside our head that drag us down. It sounds like when you move to write the novel, initially, you had to fight off those demons. You mentioned a lot of like, "Well, if we had cable TV and I've set my sights really high and I wanted to be the best," and it's like, then you just kind of wanted to watch cable TV all day. Like what's going on here? How do you win that battle? 

Cheryl Strayed: [00:55:22] I still want to watch cable TV all day, Jordan. 

Jordan Harbinger: [00:55:24] I know. I just want to Netflix and watch Indian Matchmaking.

Cheryl Strayed: [00:55:27] Oh, my gosh. I haven't watched it. 

Jordan Harbinger: [00:55:29] Oh, It's pretty juicy.

Cheryl Strayed: [00:55:30] Is it?

Jordan Harbinger: [00:55:31] It's a strange foreign world. My friend was on the shows, Srini Rao, and the mother of the girl that he dated called him Srini the Loser because he likes surfing and writing and he's creative. And the daughter was a lawyer and she's like, "Oh, this guy is such a loser."

Cheryl Strayed: [00:55:45] Oh, my gosh, 

Jordan Harbinger: [00:55:46] Tough crowd. It's a tough crowd. And that matchmaker is like, "You have to be realistic about what kind of men your daughter can get." And it's like, "Ooh, ouch."

Cheryl Strayed: [00:55:55] Well, also I love this equation that like anyone who's an artist is somehow automatically a loser because they're not making money. It's like, okay, well, I'm sorry that whole doctor-lawyer narrative — like those are the only people who have achieved anything. It's just really sad. 

Jordan Harbinger: [00:56:09] It is sad. I figured you'd have something to say about that. 

Cheryl Strayed: [00:56:12] Yeah. I mean, that's the thing. I do think that the demons and the battle between doing the work we want to do and messing around and watching cable TV and doing, you know, whatever, I think that that's, for me, I've learned that it's just, honestly, part of my process. That writing is hard. Writing is actually making something out of nothing. Nothing existed and then you put words on the computer screen and a story is made or a poem is made or a song or whatever it is. So it's heavy lifting, it's hard labor. And you also have to sort of trust that what you have to offer is going to matter.

[00:56:49] And what I found is that every day I doubt that process. Every day, I feel a sense of resistance to it, and it's easier to watch TV. And so I just have to say like, "Oh, Cheryl, this feeling of resistance, this feeling of doubt — oh, let's go do something else." And not just watch TV, you know, mop the floor or call a friend or whatever it is you do to distract yourself from the work, you know, you're here to do. If I can just say, look it in the face and say, "I see you. Welcome to the table. You're part of my creative process. The voice of doom." I call it My ITS, my Inner Terrible Someone, actually. I say, "Here you are. I knew you show up, you show up every day that I try to do my work, but I'm not going to let you tell me not to do my work." And that's my way around it. And it takes an enormous amount of will.

[00:57:32] But what I find is when I do that, it can overcome that sort of voice of doom and distraction, I breakthrough and look up and I'm like, "Wow, I just wrote for an hour and that felt great." And that's a better feeling than letting those doubts rule the day. And then you can always watch TV later. 

Jordan Harbinger: [00:57:50] Yes. That's a good point there. The TV — especially now that everything's on-demand, you really don't have an excuse to like pause right now and do it, right?

Cheryl Strayed: [00:57:56] Yeah.

Jordan Harbinger: [00:57:57] I think it's funny that you've been on these crazy journeys, 1,100 miles, toenail — six toenails falling off, and one of the hardest journeys was in your living room, trying to write and battling off reruns of Seinfeld or whatever the hell was on cable at that time. 

Cheryl Strayed: [00:58:11] It still is. You know I think that's it — and maybe in some ways, hiking, the trail was really helpful for me in that, you know, realizing like there's no way around the fact that the only way to hike a long trail or run a marathon or any of those things like that or any of those endeavors is to put one foot in front of the other and keep going. Just to keep going one foot in front of the other. And that is how it ends up. You make a life as a creative person, certainly. As a writer, it's one sentence and then the next one or the one after that and pretty soon you have something.

[00:58:45] It has some residents also just really with life. I have two kids. I have a long marriage. I have, you know, my life and sometimes it's easy and sometimes it's not and you have to continue forward. 

Jordan Harbinger: [00:58:57] What happens if you set your sights really high? You want to be the best at something you fail. You only have yourself to blame. Like how do we deal with that? Because I feel like that — I guess that's a retrospective perspective. You have to look back and see that. But I feel that way with the show sometimes, right? I'm like, I'm never doing enough, but sometimes I do just want to sit down and watch TV or like go outside and listen to a podcast and not work. But then the other part of me, there's like a constant nagging that I'm not doing enough to get where I want to be. I don't know.

Cheryl Strayed: [00:59:26] Yeah. I think it's this idea of the way we wrestle with our own ambition and success is a powerful one. And it's a question I had to answer for myself pretty early on when I was writing my first novel. When people ask me, "What were your ambitions? What did you want to be?" I always would say, "I want to be a great American writer." Women aren't congratulated for being ambitious like that. But you know, I didn't care. I always said, "You know what? I want to go to the top. I want to be great." I really want to make people feel and think big things with my work.

[01:00:01] So I set that bar really high. I studied the writers who did that to me. I wanted to be like them. And when I was writing my first book, I was when I really realized — like I was really struggling with that. And part of the struggle was I honestly confronted the fact that I had no control over that. Like, it wasn't up to me to say whether it was great or not. I couldn't possibly achieve greatness. All I could do was achieve. I could do the best thing that I could possibly do. I could write the best book I could possibly write, and whether that was going to be great or not had nothing to do with me. And I also have to make a choice, you know, and it was essentially between two things. It was, do you want to be a person who finished this book that nobody liked, that nobody published, that sits in your drawer for the rest of your life? Or do you want to be the person who never finished the novel she said she was going to write? Who always said, "Yeah, I'm still working on it." And as painful as that first thing is to write a novel that nobody likes and sits in a drawer all the rest of my life, I would so much rather be the person who did what she said she was going to do, than the person who didn't because she was afraid and insecure and didn't want to have to face the idea of failure.

[01:01:14] And so that's how I succeeded. I really wrapped my arms around this idea -- I call it surrendering to my own mediocrity. I said, "You know what, maybe I'm a mediocre writer. Maybe I am. I'm going to be her full throttle. I'm going to write this book and whatever people think of it is not up to me." And that really helped me so much, Jordan, years down the road. So first of all, that first novel Torch was published and people liked it. It wasn't a bestseller, but it was a very solid showing for a first book and I was proud of it. But then when Wild came along and was an international hit and a bestseller and all this stuff that happened to it, I felt I was so much better prepared psychologically for that success because I had already divorced myself from fame and money and that stuff being my definition of success.

[01:02:04] My definition of success was genuinely and truly, and really honestly, about the work. Had I done the best I could do in writing Wild? Yes. That was the success. 

Jordan Harbinger: [01:02:18] How do you avoid getting trapped by other people's approval? Like, yes, you can divorce yourself from success. But then also Oprah's like, "I love your books so much. I'm going to use it to relaunch my book club." How are you not like, "Okay, I'm pretty awesome." Or is that part okay? I mean, how do you know when to separate yourself from results and when to be like, "I've earned this and it's amazing"? 

Cheryl Strayed: [01:02:36] Well, I think that it's a fine point. It's hard to describe it. But I think the slight shift is that, of course, I was absolutely blown away and thrilled about that and so proud of myself and so excited. But it wasn't the thing that defined me. You know, I would have felt that Wild was a success, even if it had not been a bestseller. I would have felt successful as a writer because I had done that work. Once you can really accept that kind of thing, then all the fantastic stuff that happened. Like I felt it was like champagne on top of, you know, birthday cake or something. Do you know what I mean? It was like, "Oh, my God, Oprah and a movie," and you know, all that stuff, I was delighted in it. And I felt grateful for it and astonished by it and all those things.

[01:03:22] And of course, the success has changed my life in a lot of ways, but not in the essential ways. It didn't change who I was or how I thought about myself or how I thought about other people or how I did my work. What has changed is the fame thing. People knowing my name and financial security. For the first time in my life, I really could pay my bills and that's, of course, a big change, but it's not essential to who I am.

Jordan Harbinger: [01:03:49] I guess praise then can't be the reason that we do our work. It just can't.

Cheryl Strayed: [01:03:53] And yeah. I mean, here's the thing, of course, you know, I love to be praised. Like, we all do.

Jordan Harbinger: [01:03:58] Who doesn't, right? 

Cheryl Strayed: [01:04:00] And when I'm criticized It hurts. I mean, I think that's been, the funny thing is people sometimes forget like there's a human being in here. When people talk about writers, they'll very often — they'll tweet at me like that they didn't like my book and I'll be like, "Well, thanks." I mean, yeah, praise feels great, criticism hurts, onward we go. But yeah, it can't be the thing that defines you. 

Jordan Harbinger: [01:04:21] I know you used to be an EMT. Does that ever show up in your writing? That seems like, I mean, you're very close to other people's pain in that career.

Cheryl Strayed: [01:04:29] Yeah. Nobody has ever asked me about that. Yeah, I was an EMT for a short time. Yeah. I don't think it's shown up in my writing. I think that it was — I've always been somebody who wants to help people. I do think it's kind of interesting — like not that EMTs are necessarily like the final healers — but you know, that you're there to help. You're there to rescue people. And I think that in some ways — again, there's that metaphor — like I was drawn to that because of that impulse. And I love that about my work as Dear Sugar, that it's like my lifelong kind of desire to actually be of service in a helpful way to others is married to my life long calling to be a writer. And so like, Dear Sugar is like a literary EMT. 

Jordan Harbinger: [01:05:10] Yeah. Literary EMT, that's a great way to place it. I think in our Feedback Friday inbox, there were some questions where me and my team, we just go like, "Oh, my gosh, this person is trusting us with that. We cannot screw this up." We better make sure we know what we're talking about. Ask all these expert lawyers and doctors and people, what they think. Because sometimes we're the only people that the writer can trust with the answer. And we know that they are — if they're going to follow anyone's advice, it's this. So we can't just be like, "Yeah, screw him, cut him out of your life." Or like, "Quit that job." You know, we have to be extra responsible. It's what I imagine being a parent is like. I have a one-year-old, but it's what I imagine being a parent is like, when you have a young adult and they're asking you things and you're like, ooh, I better not just sort of fire this answer off and then get back to work. I need to think about this. 

Cheryl Strayed: [01:05:56] Yeah. Well, my kids are 14 and 16. And Jordan, what I want to tell you as a father of one-year-olds. Is that a boy or a girl?

Jordan Harbinger: [01:06:03] It's a boy.

Cheryl Strayed: [01:06:04] Okay. Give him all your advice like ASAP because, by the time they're teenagers, they're not going to want your advice. They're not going to ask you. They're not going to want your opinion. They'll just be like, "Yeah, whatever. Uh-huh. Uh-huh, I know. I know. Yeah." So do it early. 

Jordan Harbinger: [01:06:19] That's what I was like, and I know he's a lot like me. My wife goes, "See this crying storm that he's doing right now. This is you." And I'm like, "What? I didn't do anything." She's like, "No, no, no, no. This is just the baby version of you. You know?" Like I'm putting together Ikea furniture and I'm kicking it. I'm like this stupid thing, you know like I hate this. Where's the allen — oh, there it is — like, where's the allen wrench. There it is. It's just like, I've passed this down genetically. And she's like, "You have to figure out how to deal with this. Like I already have one of you." So, yeah, you're right. I better tell him everything I can before he can understand it. Now is the time.

Cheryl Strayed: [01:06:51] Yeah, put it in his brain. It's kind of like when women like to listen to classical music when they're pregnant. 

Jordan Harbinger: [01:06:57] Right, yes. We're reading to him and he's like crawling around throwing pillows. I'm like, "Is this doing anything?" And my wife's like, "I don't know everyone else was doing it. I think so." 

Cheryl Strayed: [01:07:05] Just do it. Just do it. Just trust it. 

Jordan Harbinger: [01:07:07] Cheryl. Thank you so much. This has been really, really fun. And I'm glad we finally got to do this.

Cheryl Strayed: [01:07:12] Me too, Jordan. It's really fun to talk to you. And I think you're wonderful. And thank you so much for having me on your great show.

Jordan Harbinger: [01:07:18] Yeah, my pleasure. I'm really, really happy we were able to make it happen. It's amazing you've created so many things and you've lived all these — it almost seems like more than one life, right? Like rarely do hear about somebody who's just gone through so many different iterations of themselves, I guess. I don't know. Or is that just everyone's like that and we just know more about you because you wrote about it? I don't know now. 

Cheryl Strayed: [01:07:38] I think it's a combination of a lot of things, but yeah, we all have so many stories to tell and I feel so privileged that as a writer, I get the opportunity to tell them, but I think most of our lives have many stories and, you know, we contain multitudes as a famous poet said.

Jordan Harbinger: [01:07:54] Well, have a great week, and we'll let you know when this comes out and gets edited and everything like that. 

Cheryl Strayed: [01:07:58] Thank you. Bye Jordan. Have a great day. I appreciated this. Bye-bye.

Jordan Harbinger: [01:08:02] Bye-bye. 

[01:08:04] A lot of folks, maybe even you, have asked me what my favorite episodes are of this show, and although it's impossible to pick a single favorite, I'm going to throw some trailers at the end of the episodes. And today, we have episode number 211 with Arthur Brooks, How Loving Your Enemies Can Save America. Here we go.

Arthur Brooks: [01:08:21] Anytime you catch yourself comparing yourself to others, you have to stop and say, "That's what I'm doing. Don't do that." 

Jordan Harbinger: [01:08:27] Oh, God, easier said than done.

Arthur Brooks: [01:08:29] Yeah, I know. But once you know that, the knowledge is power.

Jordan Harbinger: [01:08:32] I was just at a bachelor party and some of my friends were like, "Oh, man, some of our friends, they just became like high school teachers." And I was like, "Well, let me stop you right there. You know how happy those people are? They figured out what they wanted to do when they were like 24, they got married to somebody they'd been dating for awhile. They had kids well, before age 30, they're satisfied with what they're doing in a lot of ways. They have way more free time than you and I. We cannot sit back and judge. We're wired in a way that we're always dissatisfied. They're wired in a way where that is fine. I'm jealous of that on many levels."

[01:09:01] One in six Americans has actually stopped talking to a family member because of the election. That's pretty scary.

Arthur Brooks: [01:09:06] It's almost one in five now, yeah. Politics has become super hyper attenuated in our culture where it's taken on this outsized role and importance to assume ad hominem is. This what you were saying — it's like, Jordan, made this joke on Instagram. And so therefore I know it's residing in the depths of his heart. Like I bet you he bears animus towards some racial groups, some wild leap, but that's exactly what we're talking about. Motive attribution asymmetry on the basis of ad hominem. Don't be that guy. 93 percent of us wish the country were more united. You're part of the problem when you do that.

[01:09:42] So I got a win-win-win proposition for our listeners and viewers today. Number one is I'm going to make you more persuasive. I'm going to make you happier and I'm going to start a social movement in your heart in a tiny little way to bring our country together. And that's answering hatred with love as much as you possibly can. 

Jordan Harbinger: [01:10:01] For a great discussion and how we can bridge the divide in our relationships, our country, and even within our families, check out episode 211 with Arthur Brooks here on The Jordan Harbinger Show.

[01:10:14] That 1,100-mile hike was really something else. You know, I'm outside in my dad jeans, my shoes, my sun hat, and I'm on Mile Seven or Eight, and I think to myself, "Cheryl Strayed walked 1,100 miles and probably never dipped back into the house to grab a glass of ice tea or stand in front of the AC vent." She's known for great advice and giving great advice. Her persona Sugar is just on the Mount Rushmore of giving advice if there is one. Who else would be up there? Dr. Drew, maybe. Let me know what you think. Tweet at me. Shoot me a note on Instagram, whatever you guys want to do to reach out. I'm curious. 

[01:10:46] Don't let your dreams ruin your life. That's a quote here from Cheryl. I think it's a — it could be taken the wrong way, but what she means, again, this could be taken the wrong ways — lower your goals, so you can reach them when you need them. A lot of people have these really big dreams and there's nothing wrong with that, but a lot of times they're unattainable and it just makes you feel bad. Cheryl also said part of the weight for her pack, she brought a lot of books with her to read as a reward for hiking. Plus she loved reading and she would tear the pages out as she went and burned them. You know, can you always use a little kindling? And also she didn't have to carry the book anymore.

[01:11:16] As promised, some writing prompts. Now, Cheryl mentioned, take out your keychain. Tell me the story behind every key. There's always a story behind every key. Writing is an exercise of finding your wounds. Where are my wounds? And another writing prompt she gave is to write a woe-is-me narrative. Write down all your problems. Why everyone should feel bad for you? How your life is so bad? It's not necessarily just rolling around in the mud but it can get you thinking. And last but not least, who or what is your darkest teacher? For Cheryl, as we discussed on the show that was heroin, most likely. But who or what is your darkest teacher? Those are great writing prompts. I myself don't write nearly enough. I tend to do a lot more reading as you might imagine from this, but I love stuff like this.

[01:12:00] We should have Cheryl back some time to do an episode of Feedback Friday, speaking of advice. We'll tackle some really tough questions that come in. I think that would be fun. Let me know what you think of that. Big thank you to Cheryl Strayed. Her books are all going to be linked in the show notes. Please use our website links. If you buy these books, they do help support the show. Worksheets for the episode in the show notes, the writing prompts will be in there. Transcripts for the episode, also in the show notes. I'm at @Jordan Harbinger on Twitter, Instagram. Hit me on LinkedIn.

[01:12:25] I'm teaching you how to connect with great people, just like Cheryl, manage your relationships, using systems and tiny habits over at our Six-Minute Networking course, which is free. That's over at jordanharbinger.com/course. Dig that well before you get thirsty. Most of the guests on the show, they subscribe to the course. They're in the course, they're helping out with the course. They're contributing to the course. That's at jordanharbinger.com/course.

[01:12:47] This show is created in association with PodcastOne and, of course, the amazing team that includes Jen Harbinger, Jase Sanderson, Robert Fogarty, Ian Baird, Millie Ocampo, Josh Ballard, and Gabriel Mizrahi. Remember, we rise by lifting others. The fee for this show is that you share it with friends when you find something useful or interesting. If you know somebody who's interested in writing, creativity, hell hiking, share this episode with them. Hopefully, you find something great in every episode, so please do share the show with those you care about. In the meantime, do your best to apply what you hear on the show, so you can live what you listen, and we'll see you next time.