The Tim Ferriss Show - #231: How to Be Creative Like a Motherf*cker -- Cheryl Strayed

Episode Date: March 31, 2017

If you’re interested in the creative process of a famed author, jumpstarting your own creation, note taking, list making, or simply handling hard emotions, this episode is for you. Recorded in front of a 2,000-plus person crowd at SXSW in Austin, Texas, this one was a blast. My guest is Cheryl Strayed (@CherylStrayed), author of the #1 New York Times bestselling memoir Wild, the New York Times bestsellers Tiny Beautiful Things and Brave Enough, and the novel Torch. Her books have been translated into forty languages around the world. Wild was chosen by Oprah Winfrey as her inaugural selection for Oprah's Book Club 2.0 and was made into an Oscar-nominated film starring Reese Witherspoon and Laura Dern. Strayed's essays have been published in The Best American Essays, The New York Times, The Washington Post Magazine, Vogue, Salon, The Sun, Tin House, and elsewhere. Strayed is the co-host, along with Steve Almond, of the WBUR podcast Dear Sugar Radio, which originated with her popular Dear Sugar advice column. She lives in Portland, Oregon. Enjoy! Show notes and links for this episode can be found at www.fourhourworkweek.com/podcast. This podcast is brought to you by iD Commerce + Logistics. I'm asked all the time about how to scale businesses quickly. Rule number one: remove unnecessary bottlenecks. Many businesses can do so by outsourcing inventory management and fulfillment to a company that makes this its primary focus. iD Commerce + Logistics is just such a company. It helps online retailers and entrepreneurs outgrow their competition by handling all types of details -- from inventory to packing and shipping. I depended on iD to handle these types of details when I launched The 4-Hour Chef so I could focus on promoting the book. As a listener of this podcast, you can get up to $10,000 off your start-up fees and costs waived by visiting tim.blog/scale or idcomlog.com/tim. This podcast is also brought to you by MeUndies. I’ve spent the last year wearing underwear from these guys 24/7, and they are the most comfortable and colorful underwear I’ve ever owned. MeUndies are designed in LA and made from sustainably-sourced MicroModal—a fabric 3 times softer than cotton. Even better, it includes free shipping. If you don’t love your first pair of MeUndies, they’ll hook you up with a new pair or a refund. If you love the product, they have a subscription offer where you can save up to 33% after your first pair. Check out MeUndies.com/Tim to see my current faves (some are awesomely ridiculous, like the camo). That’s Meundies.com/Tim.***If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews!For show notes and past guests, please visit tim.blog/podcast.Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Interested in sponsoring the podcast? Visit tim.blog/sponsor and fill out the form.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissFacebook: facebook.com/timferriss YouTube: youtube.com/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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routines favorite books whatever it might be that you can apply to your own life and test as soon as today tomorrow these are the tools and tactics that count, whether they come from the world of entertainment, military, or other. And there are many different buckets of other. This particular episode was a blast to record. It was recorded in front of a 2000 plus person crowd at South by Southwest in Austin, Texas, which is one of my favorite conferences and also was the tipping point for the four-hour work week way back in 2007. If you're interested in the creative process of a famed author, if you're interested in jump-starting your own creation, creativity, note-taking, list-making, or how to handle

hard emotions, this episode is for you. We cover a lot of ground. My guest is Cheryl Strayed, at Cheryl Strayed on almost all the socials. And I will keep this short because I have another intro, which I recorded live. So I hope you enjoy this conversation with Cheryl Strayed as much as I did. And as always for a show? Alright. So this is the first live Tim Ferriss show in Tejas, in this fine city of Austin. So thank you all for coming. It's the first one. It is. I didn't know that. I'm so honored. And I am so honored to have Cheryl Strayed here. You may know Cheryl.

Hi, everyone. And for those who don't know Cheryl, I'll give you a little bit of context, and then we'll dive into it. And I will double check with the organizers, but I think we have between 60 and 90 minutes. I have a 60-minute countdown, but I think we have up to 90. So if that's too long, those are the exits over there. Cheryl Strayed is the author of the number one New York Times bestselling memoir, Wild, one of my favorites. The New York Times bestsellers Tiny Beautiful Things and Brave Enough, which has a permanent home on my coffee table at home, in fact, and the novel Torch. Her books have been translated into 40

languages around the world, probably more. At this point, Wild was chosen by Oprah Winfrey as her inaugural selection for Oprah's Book Club 2.0 and was made into an Oscar-nominated film starring Reese Witherspoon and Laura Dern. Strayed's essays have been published in the Best American Essays, The New York Times, The Washington Post Magazine, Vogue, Salon, The Sun, Tin House, and elsewhere.

Strayed is the co-host, along with Steve Almond, of the WBUR podcast Dear Sugar Radio, which originated with her popular Dear Sugar advice column. She lives in the lovely city of Portland, Oregon. Please welcome Cheryl Strain. Thank you. Thanks everyone. And there are so many questions I would love to ask but I thought I would format this a little bit differently because I know that there are so many questions you all want to ask so I am actually going to base this entire conversation around questions that you all have submitted via Facebook and Twitter and use those as jumping off points. So I thought we would start with one from Twitter,

and this is Charlie Charbonneau. I may be pronouncing it incorrectly. The question is, or one of several, is what's it like to know tiny beautiful things saved lives, including mine? Oh, that's amazing. Thank you, Charles. It's right up there with just a very small handful of the most extraordinary experiences of my life, actually. I know the power of literature because books have saved my life too. And it was always my intention from the very beginning when I first, when I was like six and learned how

to read and felt the beauty and the truth that words on the page can make. I wanted to join that club. I wanted to be somebody who would make that kind of beauty and truth in the world too. But I didn't know if I ever would be there. And I didn't know what would be the mark that I would reach that I could say, yes, I did that too. And I will say, it's that thing. It's people coming up to me and saying, your book changed my life. Your book saved my life. And so it's really the highest praise I've ever gotten from a reader in any way. You mentioned that books have saved, changed your life. What are some of those books? Are there any particular books that come to mind that have had a huge impact on you?

Yeah, so many books. Well, one of the things, I think I wrote this in Wild, that I felt that books were my religion. And what I mean by that is that, you know, I do think that there are all kinds of ways that I get spiritual solace or a sense of connectedness with others or a sense of comfort or consolation. But I would say that books have been the main one.

And the first book that came to mind when you just asked me that is Dalton Trumbo's novel, Johnny Got His Gun. Have any of you read that book? It's sadly, I think, not read by a lot of people now. But for some reason, I came upon this book when I was about 14. I don't know how it got into my hands, but it did. And it was a book that was written, I think, in the 30s. And it was this book really about a reality that was so far from my own.

And yet when I was this teenager, I really could feel the power of narrative, the power of inhabiting the life of another human. And I do think that all kinds of art gives us that ability to inhabit another human's experience, but none do it so well as books. That is literature's thing, right? Subjective truth. We get to be inside the mind of that young woman who's hiking the Pacific Crest Trail when she's 26 or the man who's in the midst of that young woman who's hiking the Pacific Crest Trail when she's 26, or the man

who's in the midst of a divorce. Whatever that situation is, we get to be in it. And so I do think that books have the power to not only remind us of our own humanity, but the humanity of others too. And that's, for me, a spiritual experience. That is what divinity is. That is what God is to me. So you mentioned inhabiting another's experience, and that actually segues quite nicely to another question, which is from a friend of mine who will remain anonymous. When one shares so much of their experience publicly, especially perhaps through writing, people who don't know you feel like they know you and often want to pour their hearts out to you. How do you connect and engage with a large audience without getting drawn into other struggles

in such a way that your time and energy are compromised? It's hard. I wonder if you also... I struggle with it. I struggle with it tremendously. Particularly when people come to me with extremely heartfelt, serious, and sometimes urgent problems. Yeah. And I'm sure you've run into that quite a bit yourself. How do you think about contending with that? You know, I don't have the final answer yet.

I think it's in progress for me. But I will say what I've learned in these years since I began writing the Dear Sugar column and Wild, and even with my first book, Torch, it was read by fewer people than read Wild, but I still had a whole batch of people who were coming to me, you know, after reading that book saying, you told my truth, you said something I feel, and no one else has ever said it. And that's a really powerful kind of intimate connection. And I think that for me, early on, I felt like, okay, we share this thing, so now we have to share more. We have to correspond or email each other or be friends or, yes, I have to meet you for coffee and talk about it. And that just became unsustainable. With Torch, the five people who read the book, I could meet them for coffee.

But with Wild, that became unsustainable. What I realized, too, is that I already gave them the best thing I have to give them. That book, Tiny Beautiful Things That Saved Somebody's Life, or Wild, that somebody saw themselves in, I gave them that thing already. Any further interaction with me will only be a reiteration of what I tried to achieve in those books.

Is my microphone messing up? It could be either of our microphones. I guess mine is attached to my head. I think my necklace is messing with it, so I'm going to put it backwards. All right, no problem. I'm sorry you don't any longer get to see the beauty of my necklace. So as context, could you describe what just disappeared behind door number one? What is the necklace?

So what this necklace is, and I was telling Tim before we went on stage, that I tend to be, one of the writing assignments, my best writing prompts that I give when I'm teaching writing is I talk about the use of objects and talismans in narratives. I think that it can be a really powerful source of story. And for example, if I made you all right now take out your key chain and then write the story of every key, you would all have written something really interesting and something very telling about your life. And so when I do things like this,

like talk to Tim Ferriss, you know, before you all, I always want to have like a talisman of what I hope happens. And so this necklace that I just made disappear, what it is is that it's a zipper that's just unzipped and it's just glued to a piece of felt. Let me show you.

See, so it's an undone zipper glued to a piece of felt. Bought at the San Francisco Museum of Modern Art. And I love the idea of unzipping. I think a lot of people, they think of going on stage and having this kind of formal interview as the time that you're going to be guarded or try to present a certain public face. And while we're doing that, I think I'm also hoping we get something beneath the surface that we can sort of unzip in some ways.

Me too. So let's get amongst it. This is, well, I shouldn't, I could say that for every single question that I'm going to ask when I look at paper because these are from the audience but in short I'm going to just abbreviate a little bit what often sets someone down a path of self-discovery is trauma so as a mother how do you work to nurture a sense of security for your children while also encouraging them to go on their own quests of self-discovery yeah Yeah, that's really tricky because my kids are like... They have the opposite life than I had as a child.

My kids are just basically little cupcakes, you know? And nothing... You know, my son, a couple years ago... My kids go to public school, but a couple years ago, we were thinking of applying... We applied to this private school, and my son had to fill out the application. And even though he was like 10, they were like, you know, describe, you know, a challenge that you've overcome. And my son was like, I don't have any, I haven't had to overcome anything, mom. You know, and he was like so

upset that nothing bad had happened to him. And I was like, my God, what an uninteresting life you have. So it is kind of funny because you're right. I protect my kids. I want my kids to not be witness to. I had a lot of traumatic things actually happen to me at a young age. And one of the great profound joys of my life is that my kids do not have that experience. I remember a few years ago, I told my kids about my father being abusive to me. I mean, it was more than a few years ago. My kids were maybe five or six when I first told them that my father had, you know, battered my mother and had been physically abusive to me.

And my kids actually thought that I was joking because they didn't understand that adults can behave that way. They didn't really actually understand that that could be true because all of their encounters with adults had been, you know, people behaving like you should behave. And so, you know, I love that we're not replicating that. And I think that, of course, like any humans, my kids will have their own challenges. And maybe one of them is just going to be like having the perfect childhood that I gave them being the perfect mother. Overcoming the lack of obstacles. Mom, what am I going to put on this application?

I made their life too easy. No, I'm kidding about that because, of course, I'm the most imperfect mother. But what I mean is I think that no matter what your circumstances are, you always have challenges, right? I mean, this is always, I mean, the human struggle is true, whether you're living in difficult circumstances or a life of luxury. And we all know that. We were talking backstage a bit about quotes that have resonated with people.

And I'd love to know, whether in Brave Enough or elsewhere, what are some of the quotes that have most resonated with your readers and fans? Oh, some of the quotes that are in Brave? That's right. Whether they're in the book or elsewhere, what has really struck a chord? Well, you know, what's interesting to me, and I say this in the introduction to Brave Enough, that I really believe that, of course, the writer creates these words and they're his or her, you know, sentences on that page. But the minute we release them into the world, they really belong to the

readers. And so I didn't know, when I was writing my books, I didn't know what quotes would be, would resonate with readers, right? And I loved that in Brave Enough, it was essentially a crowdsourced book, that I looked to the internet and said, well, what are people, you know, they tattoo things on their bodies. And one of the big surprises for me, there's lots of people who have a tattoo of the last line of wild, how wild it was to let it be. And I know what that line means to me, and I know what that line means in the context of the book. But what's beautiful about every one of those wild tattoos from that last line is that whatever it means to that individual who had that tattooed on their arm or whatever, it's not mine. It's not my story. Nobody's going to get that written on their body because it has something to do with me. It has something to do with them.

And I love that way that we can own beauty that other people have made because it lives within us then. You know, those quotes that mean something to me that other writers have written. It's not so much about their intention. It's about the meaning I took from it. Are there any other quotes that come to mind that have been particularly well tattooed or turned into t-shirts or otherwise? Well, there's a lot, you know, there's how wild it was to let it be, be a warrior for love,

write like a motherfucker. I mean, you know, very important. You know, actually write like a motherfucker is such a, has become such a thing that I didn't even, it's not even in Brave Enough. Like it's not one of the quotes in Brave Enough. I write about it in the introduction. But my favorite thing is that my book signings, people will come up to me and say, you know, will you please write engineer like a motherfucker or, you know. Mother like a motherfucker. Mother like a motherfucker. Mother like a motherfucker is another common one. And I love that because that's what write like a motherfucker means. That's what that column, I don't know if any of you have read that column,

but that's what I was driving at when I was writing about, writing this letter to this writer who's saying, I'm a writer but I can't write and I want to be David Foster Wallace, but I'm not David Foster Wallace. And I'm 26. And why aren't I famous yet? I was saying, shut up and write like a motherfucker. And, you know, I think that that applies to almost any kind of work we do. So what, can you elaborate on that? Because I'd love to hear for those people who haven't read, like, what does, what does write like a motherfucker mean to you when you are writing? Okay. It's, it's about having motherfuckitude.

Please continue, yes. Which is a combination of two seemingly opposing ideas, and that is humility, okay? Which I think sometimes gets misinterpreteded as weakness as being subservient and there's a reason we think that right to be humble we say people came when somebody came of humble means we mean they came from nothing um the word humble actually comes from the latin humus which means the ground to be down low to be the earth. And what I found in my journey as a writer is that even though I aspired to greatness, even though I wanted to make beauty and truth and all those big highfalutin things,

the only way that I could do it was to be humble and to say, I'm going to really try and I might fail. And I'm not going to feel sorry for myself. I'm going to be strong in the midst of my humility. My humility is about really forgetting about all of those glorious things that one gets when one has what we call success. Attention, fame, money, whatever, achievement. But just put my faith in the work and be really, you know, be really fierce when it comes and very exacting and demand a lot of myself when it comes

to actually doing the work. And so that combination of that kind of, you know, real strength that you have to have to do something that's hard, writing a book is hard, Writing an essay is hard. Writing a poem is hard. With that kind of sense of surrender, that sense of kind of like, here I am, I'm going to do this work and I don't know where it will lead. And acceptance. I think of humility, acceptance, and surrender as all these really words that are connected to each other in meaning. And we think of them all in these kind of, we disassociate them from things like strength and power. But I really think that the only way to get to those places is through those things. Definitely.

Yeah. Just the adaptability that comes with being able to surrender, even if it's just surrendering to uncertainty. Absolutely, yeah. If you look at, then, if we take those principles, and this segues nicely to Jody Valley-Smith, I think it is, from Facebook. Does she show up every day for two hours no matter what it takes? A few days or a few days at a time away from home?

In other words, what is your writing process? Finding space to write with mom things to do is hard. And, of course, morning routines. So I think that Jodi would just like to hear about what your writing routine looks like and maybe to make it specific. Let's say on a book deadline or on any kind of deadline. What does your process look like? What time of day? Any rituals? Yeah. So for a long time, I denied the fact that I was a binge writer. And I'm here to tell you my name is Cheryl Strader and I'm a binge writer.

I remember being in my 20s and I would go to see writers, give lectures and readings and so forth. There would always be some old guy who was like, of course I write every day. If you don't write every day, you're not a writer. And then you would look deeper, and this man would be in his office, and then his wife would bring him lunch, and then he would have lunch, and then he would write a little. And I was like, that's just not my life. Nobody's catering my life. I was bringing lunch to other people. I was a waitress. So what I found is that I creatively, and this was true before I had kids, it's true after as well for different reasons, is that I do best when I can say this is the block of time that I'm not going to be able to write. And sometimes that's like

a couple of days. Sometimes that's a couple of you know, therefore I release myself from any kind of guilt or shame or I should be writing when I'm not writing. And the counterpoint to that is to say, now I am going to write on these days or during these months. And I try to arrange my life so that that happens. And so, you know, what that looks like for me is not so much a daily practice as it is looking at the month and saying, when can I write and when am I not going to write?

And so for me, especially since I had kids, when the children came, my kids are 11 and 12, when I had kids, suddenly my whole life had to be redefined, obviously, but especially that work life, because writing is all about concentration, solitude, and silence. And those are the three things that children are most not about, you know? And I had to find, you know, a place to do that. And so once my kids were a little bit older, I had them 18 months apart. It was like a rip the band-aid off fast approach to childbearing. And once they were like two, I said to my husband, I'm going to go check into a hotel like down the street for two nights. I'm going to be gone for 48 hours. Don't

call me unless somebody stops breathing. And I'm going to work. And I would get more work done in those 48 hours than I got done for weeks at home. And this isn't to say I didn't, you know, write around the edges of things at home, but I find that when I do that immersion, it's incredibly fruitful for me. And, you know, like I said, that was true even before kids. Like, you know, I never thought of it until I had kids and actually had to get away to a hotel or whatever. But before that, I would go to writer's residencies

or I would just go rent a cabin somewhere. And there's something about that uninterrupted time to make something happen that works far better for me than that every day, like you have to write two or three hours every day. And that's just how it is. That's just my process. I had the same experience because I remember very early on,

this writing teacher I really, really respected said, no matter what, from 8 a.m. to 6, every day, I sit in front of a blank piece of paper. And I tried that. Within 48 hours, I just wanted to throw myself face first through it. Yeah. Couldn't do it. And I wanted to ask myself face first through it. Couldn't do it. And I wanted to ask

you about the hotel. So I've heard after hearing a number of writers about a number of writers doing this, I remember I hit a really tough spot with The 4-Hour Chef and I checked into a hotel in the town where I live and also got a tremendous amount done. What did those days look like for you? So you have a few days blocked out. What do the days look like? Like if somebody had a video camera and like recorded me during those times, it would look like sheer madness because I hardly sleep. I hardly eat. All I do is go on walks and write and go on walks and write and go on walks and write. There is this, I think there's something about it too that it's when you you have 48 hours or whatever number, I knew that my time was limited,

and therefore it was really valuable. And I got into the flow. I think there are different terms for this, the immersive flow, that kind of thing that happens. And I think that you need to have that thing happen for any kind of real work, but especially creative work. When you're writing, what you're trying to create on the page is that John Gardner describes it as this vivid and continuous dream. You actually are trying to

create an alternate reality for somebody else. You have to tell them what that person looks like, what that person feels like, what that person feels like, what that person is thinking, what's in the room, what does it smell like. All of those things have to come alive. And that can't come alive on the page if you aren't inhabiting that. And it's really hard to dip into that for 15 minutes at a time. And so I just knew that I had to just go all the way there during those hotel stays.

And what about you? I mean, is that your experience? Is it kind of like you're a madman? I am, and I've always... I mean, we know you are, but... I'm madman, just base level, number one lunacy, and then absolutely a binge writer. And I've always had some degree of shame or insecurity about it

because I hear about these... And I have friends who are safe journalists who say ah writer's block doesn't exist I'm like right really like am I the only one who believes in Santa Claus here yeah what's happening and I need those uninterrupted blocks of time yeah where it's very likely that the majority of the day it may look like I'm just staring off into space but if I don't have that space I'm not going to get to the writing. Well, that's right. Part of the writing is just wandering the room and that sort of thing. You know, I do think that the reason that this is important, I think, to say and talk about

is for some reason, like shame and guilt is a really big thing for a lot of writers. You know, this thing that we should be doing. And I can't tell you how many times I've told the story of being a binge writer. And somebody comes up to me afterwards and says, thank you, thank you. You know, you gave me permission to call myself a writer. And the most moving experience I had in that regard was I was giving a talk in Ohio a few years ago. And afterwards, this woman came up to me and she has, she was a single mother with four kids and had been, you know, slowly writing her novel over many years. And she worked at like a 7-Eleven or some job like that. And she was crying about this thing I had said about men's writing.

And she said, I, you know, because one thing I said is, like, it doesn't matter what you should do. Just make an intention and follow through with it. And so if all you can do is say, I'm going to write one day a month. I'm going to take one day a month. That's all I'm doing is writing. That's 12 good days a year. That's a lot of writing you can get done. And she said to me, that's what I do.

I write once a month. My mom takes my kids. And she had never allowed herself to think of herself as a writer because she'd been doing it wrong. She hadn't been doing it with that old guy who gets his lunch brought to him by his wife and said, you had to do. And I think it's really liberating to say you have to do, like with anything, writing with life, you have to do it in a way that works for you.

And to that point, I remember one of the best pieces of advice that I got when I was completely paralyzed for a period of months with just fear of writing this particular project I was working on. And the advice was two crappy pages a day. You're on deadline, but it's not going to be Tolstoy. Relax. Two crappy pages a day. You're on deadline, but it's not going to be Tolstoy. Relax. Two crappy pages a day. You might not use any of what you write for a week or two, but just put down two crappy pages per day. And what happened? What happened is some days it is two crappy pages, and it's terrible

and you don't use it, but other days you end up writing 20 pages and then there's five good pages. And it's Tolstoy. Which you transcribed from his novel. I'm working. I'm working. It's a work in progress. Question that I've actually wanted to ask you in some form for a long time.

This is from, I think it's Finja, F-I-N-J-A from Twitter. How do you get through wild or destructive emotions without destroying anyone or anything? Oh, you mean like how do you write a memoir without hurting somebody's feelings? Is that what you mean? I don't know. I think this is broad enough. How do you get through wild? You can interpret it however you might. I mean, but how do you work through potentially wild or destructive emotions? And I mean, very closely related to this is another question, which is related to pouring out your heart on paper.

I see. And whether that is cathartic, whether it reinforces maybe the pain that you're feeling, but how do you sort through difficult emotions yourself? Right, yeah. No, that's a question that comes up a lot. And I think that there are basically two kinds of people. Those who think talking about, thinking about difficult experiences or painful memories or painful

emotions is a bad thing because it brings up those feelings again. Why would you want to dwell on something that makes you cry or makes you remember that sorrow? There's that camp and then there's the camp that is like, let's dig it all up, because the only way ever to understand what happened or make some meaning of that suffering is to examine it and to look at it and to tell stories about it. And I'm definitely in that latter camp. You know, I think that, I think that, did I sometimes cry writing Wild? Yeah, I would say probably every day. You know, probably every day. And was that good for me or bad for me?

It was really good for me. When I first, my first book, Torch, is fiction, but there are autobiographical elements to it. It's a story about a woman who dies young of cancer, like my mom did. And it's kind of, you kind of a first novel in that way that a lot of first novels are, both fiction and autobiographical.

And I remember when that book first came out and I was always talking about the real life experiences that were connected to that book, people would say, was it cathartic for you to write it? And I would always say no, because I was in some ways defensive about that, maybe specifically as a woman writer, because I think whenever women in particular write about emotional things, it's put in this kind of like, oh, that's your nice little journal. You're processing your emotions versus it being allowed to be in like the sort of high art camp of great American

literature. And so I would say, absolutely not. It is not cathartic. I made, this is literature. And by the time I published Wild, I felt confident enough in my work and also evolved enough in my own life that I could say, you know, both things are true. That there is no question that the most cathartic, I would say the most cathartic thing in my life, right alongside motherhood for me, has been writing. It is through writing that I have come to understand who I am and what I've been through and therefore who we all are. And that's really been an emotional journey and one that I'm better for having taken. And yet that can also be by way of creating literature, creating art. And so, you know, I think it's good that I had to understand more deeply what happened to me. I mean, one of

the things, once you start to tell a story about your suffering, is you have to think about the people or person who made you suffer. And you start to have to empathize with them. You have to start to ask, like, well, why did this person do this to me? Or what did it mean when that happened? And, you know, I think that it really is, you know, this word healing is kind of overused. And yet, it's exactly what that is. I think this is why therapists are always, they don't put you in the chair and say, let's not talk about anything bad that happened to you in your childhood.

They say, what happened? Where are your wounds? And writing is all about that. Writing is all about where are your wounds. And you see this, I see this over and over again in teaching. This is what people, these are the stories that people want to tell. I don't know if this is true or not, but I've heard that the oldest continuously used sentence in the English language is, woe is me.

And one of my favorite writing prompts is, I ask my students, write a woe is me narrative. And everyone can do it instantly because everyone feels sorry for themselves. Everyone has a complaint, whether it be large or small. And we have lots of stories to tell about ourselves, the ways that we've been wronged by the driver in the next lane

or the mother who didn't do this or that. And I think that there's that's you know that kind of there's something good about our stories rising from those those wounded moments you have some fantastic writing prompts and thank you and there's so many of them that have made me go that could really produce something interesting such as i think i'm probably paraphrasing here but uh who has been your darkest teacher yeah which can be interpreted many different ways. What are some of the prompts that have produced the most, for you, interesting writing in your students? Oh, yeah. Well, the talisman one. When I ask people to write about an object,

so a talisman is simply an object that has accumulated meaning for you or your character, right? And so this could be, I mean, it could be anything. It could be like a cultural talisman is like my wedding ring. We all know what this means, right? And then there are other things like you don't know the meaning of this ring, okay? That's a personal talisman. And all of those things have a story attached to them. And I find, too, that when people write about themselves via a physical object, it's incredibly expansive. People are willing to say more about themselves often

when the story is about something other than them. Right, it's more indirect. Exactly. So that's a good one. The woe is me one never fails, because like I said, we can all complain. And sometimes that complaint is serious and deep and valid, and sometimes it's just like these little dumb things that we're pissed off about.

And the rants, rants and raves, we're all really good at that kind of passion. I think something like Your Darkest Teacher, that one, is a really important one to me. Because part of my, I would say one of the most significant stops along the way for me as a writer was feeling grateful for the people who taught me things that were difficult or painful or ugly, things that I didn't want to know. And actually getting to a place with them that I did feel grateful for what they had given me. So you mentioned the ranting. I want to come back to those days in the hotel because I'm so interested in process as are a lot of people in the audience who sent questions. I remember once, this is before I wrote my first book, but I was toying

around with the idea of writing and I was in an audience where Poe Bronson was being interviewed, writer, and I raised my hand and I asked him what he did when he had any type of block. And he said, I asked myself, what makes me angry? And he used that as a way to jumpstart his writing. When you hit a place, let's just say in the 48 hours that you have to write, and maybe this doesn't happen, which is a valid answer too, where you're not sure how to piece something together or it's just not flowing, what are some of the mechanisms or tricks or habits that you use to help in a situation like that? Well, you know, one of the things, I'm 48 now. I've been a serious writer since I was like 19.

And I really have learned how to remember the lessons I've learned along the way. And one of the lessons I learned is it's always hard for me to begin. And not just, I don't mean just like what the first line is of any given chapter or piece, which is always hard. But even like when you've been in that flow and then you take that break, you finish that section and then you have to begin the next. And I think that I get, it's almost like this, almost like performance anxiety. Like I'm always like, you know, what's the first thing I'm going to say when I step into the room?

Once you, right? Like that's difficult for many of us, right? It's like that beginning. You know, you know what you have to say, but how do you get to the part where you get to just say what you have to say? And so in writing, what I do is I take a shortcut around it. And when I'm feeling stuck, you know, if I don't have that first line or that first paragraph, I just say, write the part that you know. Okay. So like that might mean

it's kind of sloppy, like that I have to start writing something that's like, you know, a third of the way into the piece. Like it's a scene that I've already imagined that's going to be in there or a paragraph of just a description of something. And I find is once I start writing I relax and then of course you can go back and make that beginning you know so just begin in a nonlinear like trust that you don't have to write something in a linear fashion and sometimes that also reveals to you like a better way that the story can be told because you know chronology is always like a question in any piece you write. Do you begin here or do you begin there? And sometimes the writing process actually can teach you the answer to that question.

This is a question from Fallon Goodman, Facebook. She mentioned in a Facebook post once that she thinks about mortality daily. So, again, this may or may not be accurate. But I do, yes. Okay, great. I'd love to hear her explain what triggers them. What do these thoughts motivate her to do? What do they prevent her from doing? So can you elaborate? Yeah, that's interesting. Yeah, I did make a Facebook post one time that said that. I don't remember what compelled that post, but I know

what compelled it in my life. So when I was 22, my mom died very suddenly of cancer at the age of 45. She knew that she had cancer for seven weeks. She was like this healthy person, and then she got what she thought was a bad cold and one thing led to another and she was told that she had advanced stage lung cancer she hadn't been a smoker um and she just died i mean she just died seven weeks later and um i was a senior in college my mom was a senior in college too and what happened to me um really from that moment on is I was like, I was like not only devastated that I'd lost my mom, but I was shocked. I was young enough that I, like it never occurred to me, like really mortality, I never had to confront it.

It had never occurred to me that my mom would die, you know, at a time when I used to think she wasn't meant to die that young. I still had this kind of youthful idea that people live to be old, and of course that's what happened. And so when my mom died, I suddenly was just acutely aware that any of us could die at any moment.

And I know that it sounds strange to be 22, and rationally I knew that we could all die, but I didn't know it in my bones. I didn't know it in my bones. You know, I didn't know it in my body. And my mom dying gave that to me. And so it's true. I think what I said in that post is that every day since my mom died, there hasn't been a day that I haven't thought about my own death.

That's true. And I don't think about it in a morbid way. But I think of it in a way that I'm aware of not taking my life for granted and not taking your life for granted or any of our lives for granted. It's not, I think we have this really a problem with death in this culture. You know, we put it, we keep it at a distance. And I think even at the expense of our imagining our own mortality, like we think of this as sort of a grim thing to think about. And I actually just think it's a very realistic way to carry out throughout your day, to think, you know, okay, here I am, and I'm lucky to be here,

and let's just hope this goes till tomorrow, you know. And I think that it has given me, I don't know what the word would be, a more realistic sense of who we are and what we're doing here. And a greater sense of consequence. I want to use the word consequence. When I say bye to people, I think I try to make that connection. Do you think that's crazy? I don't think it's crazy. Goodbye is God be with you, right?

So it's intended to be, hey, I may not see you again. It's not crazy to me at all. And I had a very close friend die of cancer I didn't know about. Certainly not remotely as difficult as what you went through, but nonetheless found out late stage on a ski trip that he was going to die a few months later because he had metastasized liver cancer. Seeming, was a former super athlete. Yeah. No outward signs whatsoever.

And had a few incidents shortly thereafter, a friend, a close friend of mine from college killed himself also completely out of left field. So I, for myself, began a revisiting Stoic philosophy. And I mean, they are somewhat obsessed with death in every form, but also planting these memento mori around my house so that I would think about mortality more often. Is there a particular way that you prompt thinking about your own mortality or do you have any rituals? For instance, one thing that I do every time I'm in a plane and it's about to take off, I ask myself, would I be okay with dying right now? As a way to evaluate what I'm focusing on. And that's just a very simple way, because I travel so much, to revisit the mortality.

Right. What's your answer? Almost always yes. And if it's not, that's the catalyst for making some changes. Usually saying no to more things. Right. Yeah, me too. But I'm not okay with dying, just for the record. Now, I should clarify, being okay with dying, just for the record. Now, I should clarify, being okay with dying, any crazy stalkers in the audience, means not that I want to die. If you try to kill me, I will throat punch you. But that it's a way of

gauging how true I am being to the things I claim are important to me. Yeah. No, I get that. Yeah, to me, it's not, it's more organic. Like it really is just an awareness because it sounds, I want to return to this thing I said where it never, it had never occurred to me that my mom would die. And of course I'm being hyperbolic. It had occurred to me. Um, but I, it occurred to me in that same way, like that most of us go along in our lives feeling rather complacent, right? That like, you know, it could happen, but it, it occurred to me in that same way, like that most of us go along in our lives feeling rather complacent, right? That like, you know, it could happen, but it probably won't. So let's like, let's just push that really far.

And so at this moment, you know, when my mom died, I was, like I said, a senior in college. I was also in this moment of, of my life and all of our lives when we're in our early 20s, where you're, you're trying to figure out like who you are, you know, coming into your manhood or your womanhood, and that's what was happening to me. And it took me, one of the most fascinating processes I ever went through was actually letting go of my mother. And even like I had months of just dreams about accepting my mother's death.

And the dream that I had over and over, which I know is the boringest thing in the whole world to have somebody tell you their dream, but I'll just keep it quick, is that I had to murder my mother. Over and over, I had to kill her, had to beat her to death, had to bury her alive, had to run her over with a truck, had to do terrible things to my mother. And it was just like because I couldn't believe she was dead.

And I think that what I've come to know through my work is that, you know, I've talked to so many people who have experienced deep grief, and they also went through that. And, you know, it's something that for whatever reason, we don't really know how to talk about in a public way or to sort of bring into the fold of like what it means to what human experience is. And so it's, to me, my awareness of my mortality is, it's just more, it's something that I notice in a way that I didn't notice it before. Instead of choosing that sense of complacency, like, well, that won't happen to us. It's living in that place where you say, yes, it will, every single one of us right here in this room,

every single one of us, we're going to have that shared experience of dying. There's a really fascinating experiment that was done, I want to say it was NPR, but there were these dinners hosted around the country called Death Over Dinner, and there were discussions about death because, like you said, it's a subject that I think is underexplored and underdiscussed. And then people are caught very much unprepared for the emotional hardship and everything that goes with mortality. This is a question from Jessica Larson from Facebook. Were there ever dear sugar questions that she felt unequipped to answer?

And in general, did she have a particular process for answering the questions? Yeah. You know, many times, so I used to write a column, the Dear Sugar column, but now I have this podcast. And, you know, there are definitely questions that are like, wow, I don't know what to say. You know, I don't know what to tell you to do. One of the things I've always positioned myself as when it comes to giving advice is sugar, is it's not really, I'm not trying to tell people what to do. I'm trying to help them ask deeper questions. I'm trying to help them help illuminate maybe. Sometimes people think that their question is this, but it's really that. And I think of myself as somebody who's trying to illuminate a conflict or a struggle by way of giving advice. And there are some times where it's just impossible. I would

say, you know, the few times, both in the column and then now on the radio show, that I've received a question from a woman who is pregnant and doesn't know what to do. Like, have an abortion, have the baby, and then give it up for adoption or keep the baby. I'm thinking of one woman right now wrote to me with that scenario. And I broke my own rule in this one question. I responded to her personally. Usually, I only respond on the show or in the column. And I emailed her personally because I felt like she was in a really desperate situation and needed help. But I also wrote to her to say, like, I could not possibly be the person.

Nobody would be the person who could tell you what to do. Because there are some decisions that have such high stakes and such personal consequence that only you can say. So those are really hard ones when it's a, you know, that's a very black and white decision, right? Whatever that person decides, that's, you know, really a big deal. Usually the kinds of questions we get. Not to interrupt, but I will. How do you help someone and say an email that you send to her to process that?

How do I help? Help her to process it like you mentioned because i think you're very good at it and you say you of course mentioned the email i can't make this decision for you but is is there more to the email yeah yeah no it's like one of the longest emails i've ever written so um what i did is i walked her through my thinking about the consequences of each decision and you know I said you know these are the things this is this is what you know I did with her the way I would do it in the column which is like okay so you know what are the reasons that you would do this or that or the other

thing and I you know we I laid all the scenarios out. And I think that that's, in my own life, always what I do when I'm having a hard time. And I talk about this a lot on the show. It's like I'm a super big fan of list making. I'm like the list queen. And every problem I've ever had has been solved by a list. You write down all the reasons for this and all the reasons for the other thing. And then all that, you know, and it's like, yeah, and there's sub lists and, you know,

you could color code them. You could get highlighters and the answer is there. Okay. We have to do a deep dive on the list. I know you're going to make me talk about that. I would love any example of yours. Okay. And what was the challenge or problem or question, and what did the lists look like? Well, you know, I mean, it's so hard to pick one because there are so many times. Okay, oh, this was a big one. Well, speaking of kids, so I have two kids. So when I was almost 40, I thought that I was maybe pregnant again. And it wasn't planned, but it was kind of like, well, maybe we should have a third kid.

And so my husband and I were agonizing. We're like, well, what do we do? A kid is a big deal. Do we want a third kid? And so I made a list list and it was like everything, all the reasons I didn't want to, all the fears. And what I mean that there are sub-lists is like, well, why are you afraid of this thing? Like sometimes the thing that you're afraid of that's like on the no side of the list can actually be solved by another list because

you can solve that problem. Meaning that you would say, why am I afraid of X? Why am I afraid of this? And once you make that list, you realize that it's not scary? Exactly. Or you can say, okay, well, this can be addressed. You know, like, oh, I don't ever have time to write. Well, we could do this or that. You know, it allows you to sort of see instead of just feel what your challenges are. There's something about having it in front of you that in some ways, it pins it in place

rather than allowing it to float around in your head and be this big, terrible monster thing. Nebulous. Yeah, and then the reasons to do it and the reasons not to do it. And those are really, I think, they allow you to kind of see, it's literally like a map on the wall of your life.

You know, what you want, what you fear, what you desire. And I think that those things, that we make them very explicit rather than just imagined, a list does that. I do something very similar, actually. When I'm afraid of something, I'll ask, it's effectively the worst case list. What are the worst things that could happen if I did X, which I kind of want to do, but I've been putting off. And then how could I mitigate the risk of all these horrible things from happening one at a time? What could I do to get back to where I am now? It usually ends up diffusing in some way. A lot of the things that I expect are going to be these insurmountable problems,

which are in fact just nebulous and need to be. Very much so. And often, you know, sometimes too, you know, like there could be, I did, we did end up not having a third child. I wasn't pregnant, you know, and we decided not to, but what was really striking to me about that list and the reason I brought it up is that there was only one thing on the list of reasons we should have a third child. And there were like 300 things on the list, but the one thing on the list to do it was more important than any of those other 300 things. You know, is that a visceral, is that a instinctive perception or is there some way, is that just a feeling that you have in terms of the importance of that one versus the 300 no the importance of that one is that you know having

like my my husband and i made this list together it was like having our kids is the best thing we've ever done bar nothing you know so it was just like a very clear truth um that was standing at counterpoint um to these like, you know, we don't have as much time as it is, and we won't be able to sleep for another two years, and all of that stuff. And so, you know, obviously, I think that this is often true when I've had professional, I've been at sort of crossroads

when different opportunities have come my way. You know, here are the reasons to do it, here are the reasons not to. It's not about the number of things on the list, it's about the weight of those things. And almost always, I think the things that mean and matter the most really come down to sort of one question, what do you really want to do? And this is something that I really believe to be true. And I have the privilege of seeing letters from so many people who write to Dear Sugar. And almost always in the letter of the person who's saying, I don't know what to do. And I have this problem.

And I don't know if I should break up with her. Or if I don't know if I should take this job or move to New York City or go to Paris, whatever it is. The person who writes the letter almost always knows. And I think that one of the scariest things in our lives is actually doing what we know we want to do. Most of us don't give ourselves permission to do that. Most of us take many years to do that. You said earlier one of the hardest things for you

was to learn how to say no. Still is. And that's me too. And that's about giving ourselves permission to do what we want to do. And it's because we associate that, like even that phrase, like when I say doing what you want to do, I'm sure some of you in the audience think, well, that's very selfish. We associate that with being selfish. And it's kind of like the way humility is strength, vulnerability is strength. Those two seemingly opposing things sit opposite each other. They're also the same thing. I really think there's something about this, you know, that actually

doing what you want to do is the opposite of selfishness. It's actually a kind of generosity because you're being honest. You're being, you know, you're saying this is what I need and I won't expect you to do something you don't need to, you know. What have you learned about your journey to saying no? I've come to a very similar conclusion. Now that doesn't mean it always translates to the action, although more and more it does does what I've realized for myself is that a and what I've observed just in my female audience is that many mothers have also come to the same conclusion that they don't keep if they don't take care of themselves they cannot most effectively take care of other people uh So I do not have kids, but I feel an obligation to act on behalf and do

things on behalf of, say, my readership and my listeners. And there have been points in the past where I've made some very unwise sacrifices and compromises with health and otherwise, not to mention all the harebrained physical experiments that I've done. But putting those aside, I think just remembering that if you don't protect the vessel, you're going to ultimately in some way hinder everything else that you want to do for others. So that's part one. Part two is that I've realized for myself in the saying no thread that there are certain things that I can moderate well, and there are certain things where I'm very binary. And that if I say yes to one, I'm going to suddenly open the floodgates and be more prone to saying yes to many, many things. So that is why, for instance, I stopped across the board

doing any startup investing. I was involved with technology for a long time, for about a decade. And I realized that as soon as I let one in, I'm going to feel a compulsion to compare it to everything else that has come in. And all of a sudden I'm looking at hundreds of emails. And that I don't do moderation well in that sphere. So it's either a yes to opening the floodgates or it's a no to everything. And trying to be as honest with myself when I journal, say, to clarify my own thoughts or make lists. I also have a hypergraphic tendency to create lots of lists. To try to be as honest with myself and in longhand explore what I am good at moderating and what I'm not good at moderating. And whenever possible in the things where I'm not good at moderating, saying no to

everything in that category, unless it is of primary importance with the answer to the, what do I really want? Which I think is this, for me at least, a surprisingly tricky question at times. Right. And yeah, obviously, and we're also, we're not talking about like, I want a hot for Sunday right now, so let us go get one. I mean, I'm not talking about that. When I say to do, you know, that most of us take a long time to learn how to say what we want. I mean, for those, those bigger things like that, you know, for me, it's been very connected to what I give beyond like the books I. How do I keep that line of communication open between the readers and the writer? And how do I also have my own private life?

And it's tricky. It is tricky. For those people who are wondering and here in person, we are going to be doing a book signing at the book signing location after this session. So there's that since it's related, but I would love to ask you who you, not who, but what type of people do you go to for advice? So you were very good at giving advice. When you need advice, what type, what are the characteristics of the people you go to? And how do you elicit advice? You know, I think that maybe what helped me sort of have the audacity to even begin writing the sugar column,

because, you know, of course, the first question I asked myself when I agreed to write the Dear Sugar column is, who the hell am I? You know, why would I think that I could give anyone advice? And, you know, what I realized right away is, first of all, I never positioned myself as the authority on anything. And the reason I could do that so comfortably is much of the best advice I've received does not come from somebody who has a credential to give advice, right? I mean, obviously, I think that psychologists and therapists can give great

advice and do, and they absolutely serve a function. I'm not questioning that at all. But I also think that most of us get wisdom from a wide range of sources, from the people we know and love, from strangers on the street, from therapists and counselors, from teachers, from books, you know, from podcasts. And so, you know, I turn in all of those directions. When I find that I'm stuck, for example, this question of no has been a big one for me over the last few years. I have asked Oprah how she says no. Good person to have on your speed dial.

That's true. That's amazing. No, no, that's a great person to ask. But I've asked Oprah, who, let me tell you, has some really interesting things to say about that, which I know is shocking to all of you, right? I've asked, you know, friends. I've asked people at parties who I met, you know,

like we get on this subject of no. I think a lot of people struggle with this question. You know, we all have different relationships to what kinds of things are being asked. But almost everyone has something to tell you about it. And, you know, I think that to me that's always too, when I'm giving advice, I always feel like I'm just one voice and I encourage people, don just listen to me I'm gonna offer you what I can offer you and then somebody else it's not about being right or wrong it's about illumination it's about getting you as the person who's seeking advice to ask deeper questions

to bring into consciousness maybe a little piece of this that you didn't see before you talk to me and I love. I love that about both advice giving and advice taking. It's also, I mean, the approach that a lot of successful crisis hotline operators use in the sense that they're not trying to give a solution to a problem. They're trying to defuse acute reactionary impulses and help people to illuminate what it is they're feeling and thinking. Well, you know, I think too, I would say that maybe the most important kind of thing that people take from my advice is just that sense that they're not alone. They're okay. Even when you just, when you said earlier that saying no is hard for you. If there were little nodes attached to my brain,

some little pleasure center would have been bumped up then. Because it's like, OK, oh, yeah, so you seem like this together person who's successful and making it happen. And you clearly know how to say no. And then when you say, I don't know how to say no either. It's a struggle for me. It's not advice that you've given me, but it's a sense of consolation. It's a sense of being part of a struggle. And I think that that's

also what we seek when we seek advice. Nobody can tell us to end our marriages or do this or that or the other thing, right? But we can say, you're not alone, and I too have had that struggle. So you mentioned marriage. I'd love to ask you a question that was both a lot of men and women wanted to ask in some form or another, which is, why did you stray? Why did I stray? Because this is something that people have either experienced on one side or another, or have as a fear or a thought or a desire. It's a very, this is not a new phenomenon.

Why did I stray? I strayed in a number of ways, but yeah, I think with that. So, you know, because I was young, so for those of you who don't know what this question means, I was, as I wrote about in Wild, I was married young, and I just, my mom died, and I just couldn't stay in the box, in the box that my marriage was in, that my life was in. So many of the, so much a part of my growing up, I think, especially in my 20s, doing that real adult growing up, was about testing the fire and seeing what it felt like to do something that I wasn't allowed to do. And maybe that was, that thing that I wasn't allowed

to do was what I wanted to do and seeing what it felt like to do that. And, you know, that thing that I wasn't allowed to do was what I wanted to do. And seeing what it felt like to do that. And, you know, it was really painful and interesting and necessary. So that's why I strayed. And, you know, it led me, and of course, like almost always, when we make mistakes that harm ourselves, it almost always leads us to, if we listen to that lesson. I mean, in some ways, that was a dark teacher, right? It led me to this place that I could then make other choices,

walk in a direction that was going to be not about increasing my suffering, but rather lessening it. Mm-hmm. So this is a question from Max Alpert. If she knew that there were people listening who are currently hiking the Pacific Crest Trail, like me, is there anything she would say to them? Oh, I wish I were with you.

That's what I would say. You know, one thing that every, I've talked to so many people who've hiked some long distance trail or gone on even, you know, just a few weeks backpacking trip. It's always like the best thing any of us have ever done. And I don't understand why, because it's also really technically quite miserable. I mean, you have to like poop in a hole that you dug yourself with a stick. And you have to like sleep on the ground and it's cold and it's hot and it's all of these things and you have to sleep on the ground, and it's cold, and it's hot, and it's all of these things, and you have blisters.

But really, there's something about that kind of doing something hard, making yourself suffer in a physical way, that feels like the opposite of suffering, incredibly restorative. So I have such nostalgia for my time on the Pacific Crest Trail. Any piece of advice that you would give people on the trail? Or maybe, I'm just making this up, but a third of the way through, who knows, a week through, and they just are thinking of packing it in, calling it a day. Well, you know, it's not just long-distance hiking, but certainly long-distance hiking.

But I think any kind of journey, any kind of trip you're going to take, to remember that it's not, that it's, that usually it's not going to be fun all the time, and sometimes it's not going to be fun a lot of the time. Almost always when we're about to go on a trip or a journey, we imagine, like what we're imagining are those like sort of postcard scenes that we think we've gone to, you know, Bucharest for or to the PCT for or whatever. And then you get there and it's like, you know, it's not like that. But what I always say is I'm a real believer in retrospective fun. And that is the fun that you have remembering the like shitty thing that happened. This is really... If I asked you to tell me about some of your travel experiences,

I guarantee you the things that you remember the most acutely are the time you almost died in Guatemala because you had such terrible diarrhea for a week. The diarrhea stories, they're our best travel stories. America's best diarrhea essays. Everyone remembers, right? You remember that horrible, you know, my husband is a documentary filmmaker

and he was making a documentary in Cambodia and he ate something and he went to bed and he was so sick that he literally shot the bed. He woke up. My kids, that's their favorite travel story. They're like, tell us again, Dad, about when you pooped in the bed.

And it's like, and this is really true. And same with the Pacific Crest Trail. You know, what did I write about? The funny thing about when I was writing Wild, I have my journals. And I was reading my journal, like, you know, what was I writing about on the PCT as part of the research for my book. And, you know, like literally half the pages are me complaining about how much my feet hurt, you know? And it's because that's, you remember your suffering and it becomes pleasure afterwards. Do you, is that true? Oh, I absolutely have it. So I think of the retrospective enjoyment, and I also think a lot in my own life and for my family, meaning my parents and siblings, of perspective enjoyment.

So I try to schedule one or two events or trips with my family per year, and this is relatively new in the last two or three years, so that we we have even if the event itself is a disappointment at the time although i hope it not to be and i try to make it fun that we have say six months to look forward to the trip and then that trip happens and then six months hence we have another trip scheduled so we can look forward to it and plan it and look at photographs. And I really feel like, this is an arbitrary number maybe, but 80% of the fun is looking forward to it. Okay. So I'm retrospective fun. You're anticipatory fun.

Sounds like it. Yeah. But the trip always sucks. I do my best to have the trip also be fun. No, I know, I know. I hear you. On occasion, like when I went to India, and you want to talk about diarrhea stories, and I get stuck with typhoid fever effectively in the ER in Calcutta for a week, makes for

a good story. That's right. It wasn't very much fun. If we locked the doors and made everyone get in a circle and we would spend the night going around the room, everyone tell their poop story, you would all have one. And it would be very fun. If you could, or let's just say you had the opportunity or the obligation to assign one or three books as a gift to every graduating college senior. So some philanthropist says, all right, I'll pay for it all. One to three books that you can give to every graduating senior.

What books come to mind? See, I was all ready to say my favorite books, but now with the graduating senior thing, you made it. The first book that came to mind would be Claudia Rankin's book Citizen, which came out a few years ago and is just a really important book for us to be reading right now. But, you know, one of my old standbys, too, is my favorite, Alice Munro is my favorite writer, her selected stories. My favorite book is her book, The Lives of Girls and Women. But she's just an amazing short story writer.

I love her so much. I'm also, you know, I love so many poets. Mary Oliver is one of my favorites. I mean, it's always hard for me to think about forcing one book on everyone, but all of those would be good ways to go. What do you like so much about Alice McGrath? Wow.

I don't know if anyone's ever asked me. She is... I'm glad I got one. I know. What do I love about her? She is the kind of writer who... I've read all of her stories many times, and almost always the experience is,

like, I'll be just going in to try to find a passage or a quote, and I find myself, like, accidentally reading the whole story again, and every single time it takes my breath away. She's so... Her craft is so... She's such a, you know, virtuosic prose writer. She has the capacity to inhabit, you know, a sense of perception that exceeds even what we already know to be true. And when you see writers do this, what I mean by this is like a good writer can make you feel what it feels like to be, you know, feeling unwell in Cambodia, right? You can be inside that physical experience. You can

hear the sounds and the smells and feel like what they're thinking of that moment or that situation. And Alice Munro and a few other really great writers can transcend beyond what you already know that experience would be like and actually show you a deeper level of that experience. That's, you know, when we say I was astonished by this, what we mean is we were shown a truth that we know is true, but couldn't yet articulate to ourselves until it was shown to us by that writer. And that's magic. I mean, that's a magical act. And I think it's what every writer aspires to do. It's certainly what Alice Monroe has done in pretty much every one of her short stories. When you hear the word successful, who or what

comes to mind for you? Well, you know, I'm just a real believer in many different definitions of success. You know, I know I'm not the first person to say this to you, but this idea of our culture has created this notion of success that has to do with money and position and sometimes fame, depending on what your career is. And I reject that. I don't think it's successful to be at the top of some pile and have a sad, pathetic life. I don't think it's successful to have a bunch of money

and be mean to people. I really take very seriously my values, I guess, that have to do with not just achievement and following through on the things I said I would do professionally, but like the way we are and the way I act in the world. You know, are you kind? Are you honest? Are you generous? Are you transparent? I think transparency is something too that's like a sign of success, a mark of success. And I think to me it really comes down to a couple of questions. Did I set intentions and did I follow through with them? Did I do what I said I would do?

And every time I've done that in my life is when I feel like I've succeeded and every time I have not done that in my life is when I feel like I've failed. And that's in ways large and small. What is something you're currently trying to improve or something you're struggling with? And how are you going about it? Well, I have spent most of the last week cleaning my closet like a motherfucker. Because things have gotten out of control in my life, Tim. I'm a little bit like, you know, it's like, you know how this stuff, the stuff is encroaching. And I realized it was actually like, you know, violating my psychic space. And I needed

to just like once and for all. And that's, I was feeling like a failure because I kept saying like, I have to deal with all this junk I have. You like the old lego pieces that my kids don't use anymore and the old whatever like this this pants I'll never fit into again or whatever and I finally just like went I was just like went through all my stuff I even hired like these guys came and like reconstructed my closet like physically like you know reconstructed my closet and then I got it all like together and I brought my daughter into my closet to show it to her and she said mom it's like Pinterest so I'm very proud of myself I'm a success it's like Pinterest that's it that's how you know and if you you I know

you sometimes ask people like what's the purchase under a hundred dollars or whatever right you've made most possibly impacted your life okay let me tell you guys i didn't know this until last week there's a thing called a boot box for your long boots and you put your long boots in them instead of draping all over the floor of your closet and and then you put them up on the shelf. Bootbox. Like Pinterest. It costs like $10. What is something, or maybe there are multiple things, something absurd that you love doing? Something absurd that I love doing? Yes. And I'll give you an example because I was asked this recently and it caught me off guard

and I thought about it and I realized I have this habit of whenever I'm feeling stressed or very often I don't know why I do this but I go and I stretch my jaw and sometimes it's in public and I open my mouth like a yawning lion but it could be at a bookstore and then you'll see mothers like guarding their children because I look like a lunatic so I think that would fall into the absurd category I think it's because I clench my teeth at night but certainly looks ridiculous it doesn't have to be that odd but is there anything absurd that would fall into the absurd category. I think it's because I clench my teeth at night, but it certainly looks ridiculous. It doesn't have to be that odd.

But is there anything absurd that you love doing that comes to mind? Oh my gosh, this is a hard one. Nothing comes to mind. I do tend to be a little obsessive. Like, if my kids are eating Skittles or M&Ms or something, which they're not generally allowed to eat so much, I'll have to organize them by color.

But I don't think that's absurd. I think that's perfectly reasonable. I mean, why would you want to eat the colors out of order? Makes sense. No, this is, I thought of something. This makes my husband crazy. So I, like, sandwiches, I'm a Virgo, and I like things to be ordered. And so sandwiches are, they, they, they're greatly

problematic for me because, you know, because you might like, here's my whole theory of the sandwich. And I think that there are people who have a different theory, but maybe a couple of you have my theory, which is every bite should be as much like the previous bite as possible. Do you follow? Yeah. So you need an everything bite. Okay. So like, what if there's like a clump of like tomatoes here, but then there's like some, you know, hummus over it. Like everything has to be as uniform as possible. So any sandwich I'm ever given, I open it up and I immediately like completely rearrange the sandwich.

And then I close it. My husband's always like, would you stop touching your food? And I'm like, you're just jealous because I haven't done this to your sandwich. And he's like, get your hands off my sandwich. So do some of you also believe in this uniform sandwich idea? Look at this. It's like 70% of the audience. Who knew?

So is that absurd, though? Who thinks that's absurd? Well, I think absurdity depends on the belief of the majority. So apparently, with this audience, it's completely normal. That's right, they're on my side. The audience is full of Virgos, I can see. Do you believe in astrology? I would say generally I do not.

But I don't know anything about it. I will say anything I know about it, I've been told by other people. And so you don't believe in something you don't know about? Well, I would say generally I have a high degree of skepticism related to astrology. I'm open to input, but generally, I'm a pretty literal sort of falsifiable hypothesis kind of guy with labs and blah, blah, blah, which can be very boring, but that's just my hard work. Yeah, no. But then again, I live in San Francisco and I can get pretty far out in the woo-woo territory with other stuff, which probably makes me a total hypocrite.

Favorite failures. When you think of, is there any favorite failure or any failures that come to mind that looking back set the stage in some way or planted the seeds for a later success, or just a fantastic failure story? It's interesting whenever you ask a writer, I guess except for those few writers who come out of the gate at 22 and they win the National Book Award or something, that it's not one story. It's like a decades-long journey of being told, you didn't do enough, or we don't want you,

or you're not going to be included, or we don't want to buy this or that or the other thing. I think that part of being a writer and probably any kind of artist, you have to sort of always be hearing that something's not good enough, even if it ultimately is, when you're being told, okay, this is great, now revise it. This is great, now revise it. This is great, now revise it. So failure is just like literally part of my life or part of the vernacular, I guess.

But I will say that I have had a couple of experiences that were, in retrospect, kind of helpfully crushing. And they always served that purpose that I spoke about earlier of like reminding me what I was really doing and why I was really doing it. And it was reminding me to be humble and to not take for granted that I was going to be loved or that what I made was going to be loved, and to not take for granted that I was going to be loved or that what I made was going to be loved. Because the thing about making art is that you have to be committed to making it even if you aren't loved.

And so you have to attach that engine that drives any of us forward in the work we do. It can't be connected only. I mean, obviously, we all want to be loved. Me too. But the driver of that engine cannot be that other people accept and love you connected only. I mean, obviously we all want to be loved. Me too. But, but it can't, you know, the driver of that engine cannot be that other people accept and love you and praise you. It has to be that you really want to do this work. You really want to make this thing in the world. And, and so the times early on, you know, I remember when I was in graduate school, I had a

piece, you know, I was, the writer's failure stories are always so boring. It's like, you know, oh, an agent and all these agents loved that piece and they all wanted to see your work. And then I was like, oh, here's, you know, the first hundred pages of my novel, which weren't really ready to be shown yet. And, you know, they all were like, thanks, but no thanks. And, you know, I went from feeling like, oh, I'm, they love me to, they don't love me. But, and that hurt in the moment, but at the time, in retrospect, I think, oh, that was really a great lesson because what I did then is I said to myself,

I will never again show an agent my work until I really can feel like it's ready to go. And that's advice I've shared with a lot of writers. When they say, well, how do you get an agent? Or what advice do you have? My first advice is always like, make sure your work is ready to show, you know, don't rush. You know, most of us rush for that external approval. I understand that impulse, but it's almost always the wrong impulse. Yeah. I think that there's a conflict in many people's minds between, say, the, I think, over-romanticized, say,

Silicon Valley notion of, you know, fail fast, fail forward. If you're not embarrassed by the first version of the product you ship, you shipped it too late, which I think does apply to certain things like software in some cases. But I was talking to, and I won't mention the name because it's a private conversation, but a very successful stand-up comedian. And I asked him what advice he gives to novice comics. And he said, don't move to New York or L.A. until you're good. Yeah. He said, get good on the smaller stages first, and then you can go play in the big leagues.

But until you're ready, don't step onto the stage in the big leagues. But until you're ready, don't step onto the stage. Yeah, I think that's really interesting. And it's interesting to me because I really agree with it. This message that we're hearing a lot in the last few years is like, failure is good and failure teaches us things. And like, I believe all of that deeply. But I think that what gets lost in the translation is that there's a difference between failing and being sloppy and expecting other people to do your work for you. And I am a real old school believer in craft when it comes to stand-up comedy or writing or developing software. Actually, really, genuinely doing your work, apprenticing yourself to the craft of like what it takes to make that work and what it takes to make it good. And, you know, then go forward and fail. There's

still plenty of room to fail out there once you know what the hell you're doing. But this, you know, I do see this sometimes with people who approach me where it's like, they actually haven't done their work. They're approaching me in this spirit of like, well, you know, like failure teaches us things. And I'm like, but no, you, I'm not going to do your work for you. You've got to do it for yourself. And I'm kind of an old school, you know, sort of stern in that regard, you know, that regard when it comes to that message about what failure means and what it can teach us. Well, I was chatting with, in this case, it was a lawyer, very successful lawyer, who was talking about, at one point, drafting some type of document for one of his professors.

And the professor would say, not good enough, do it again. Not good enough, revise. And I think it was three or four refusals like that and requests for revision before he, the professor actually looked at the document. And in fact, he hadn't looked at it at all. He just wanted it to be in tip-top shape, and it was. That's great.

But I'm not saying he should by default do that as a teacher, but the fact of the matter was this particular person who went on to become a very good lawyer was able to dramatically improve what they delivered. Yeah. Well, and I think that that's what we should do with ourselves, is you finish that first draft and say to yourself, not good enough. What can I do on that next round?

If you had a huge billboard, and this is more of a metaphorical question than anything, but that you could use to get a short message, question, anything out to millions of people? What would you put on that billboard? Oh, you know what? I think it would be this thing that I learned when I was writing my first book. It would be surrender to your own mediocrity, Which sounds kind of sad, right? I mean, we're supposed to be, you know, aspiring to our greatness. But I think that here again,

this idea of humility and strength is connected. Because what I learned, you know, when I was writing my first book, I really felt like, okay, I'm going to try to write the great American novel. Like every writer who is, you know, is like, I, I'm going to try to write the great American novel. Like every writer who is, you know, is like, I want to be that. I want to write the best novel that has ever been written. Even when I knew that I probably wasn't going to be able to do that, that was where I aspired to

be. I was like, you know, there's this American idea, right? Like that you reach for those kinds of heights. And I found when I was about two thirds of the way into that endeavor, writing that book, that idea of greatness was what was actually keeping me from fulfilling this dream. You know, and that what I had to do was that humble thing where I say, guess what? It's true. I might be writing a mediocre book. I might be writing a book that nobody ever reads. And I just have to surrender to the truth of that. And I have to surrender to this notion that even if I'm mediocre, what matters more to me than writing a great novel is writing a novel. And that was a huge lesson. And it was a lesson later when I was thinking so much about my hike on the Pacific Crest Trail when I was riding wild.

That was something that I learned every day. I would be like, I'm going to try to do this much, and then I have to do this much because this is what I can do. learn that like when it's not about it's not about so much accepting a limitation rather than as accepting um that by doing the best we can do that the work that that we have to do um but that's the only way to get to greatness you know and that we aren't the judge of our own greatness we're only the judge of like our intentions and follow through i love. And we also take the off the performance anxiety and pressure with this label of greatness or aspiration of greatness that ends up producing exactly the opposite sort of a choked, overthrottled attempt that is full of fear. Yeah. I think that, I mean, I'm all for having those big dreams, but I do think

that at a certain point you can let your dreams get in the way of the actual work you need to do. What advice would you give to someone who came to you and said, I wrote a memoir, successful as a book or not, that is being turned into a movie? What advice

would you have, or what would you prepare them for? Well, first I would say be very, very, very careful about who you trust to make that movie. Like, you know, that you, for me, having that sense of like really trusting that my book was in the hands of people who were good humans and who were going to be good for their word, who pledged Reese Witherspoon when she first read Wild and asked me about her being the one to bring it to the screen. We had a deep, long talk about what the book meant to her,

why she felt like she was the person to play me and to essentially midwife that film as the producer into the world. And also that, and what, you know, what values she would hold true throughout that process. And she was, she was, you know, she followed through. She, she actually pledged to honor the book and she did. And I think that that's really important. It felt really vital to me that, you know, I had the opposite experience in Hollywood. Many, many writers tell you terrible stories about what happened to them in Hollywood. And I have to say, like, from from Reese, to the director Jean-Marc Vallée, to the screenwriter Nick Hornby, to the studio, Fox Searchlight, all of those people were creative, good humans

who had depth of character and really cared about not disrespecting what I'd written. That in so many ways, it wasn't obviously they can't make my, you can't have everything in the book in the movie, but that they cared about the spirit of my book. And that mattered a lot to me. And I think in my friends who have had opposite experiences, it's that those, all the people who are making that movie, they don't really care about what's happened in the book. What they care about is that product they're making as a film. And I just don't think that that ever leads to

good things. And so, you know, I think that that kind of old-fashioned trusting people who are good for their word matters a lot. So I have a tremendous amount of respect for Reese and a lot of people who are involved with the film. That said, Hollywood is full of people who are very good at making empty promises. Yeah. So what were you looking for in those meetings? Authenticity.

Was it just a spider sense that you had? Yeah, it was a spider sense I had. And I really do have that. I mean, it's one of the areas that I would say that I actually do feel like I get a sense of people. And I got a real sense of Reese. And I could tell I trusted her. And one of the first things that I felt about Reese is she was immediately open and vulnerable with me in a way that you would never expect a movie star to be. And, you know, you asked me

this earlier question about, you know, success and who comes to mind when I think of success. And I think of Oprah Winfrey, and not for the reasons that we all think, because obviously Oprah Winfrey is wildly successful. But one of the things I never forgot is the moment I met Oprah, she had picked Wild for her book. She was restarting her book club with Wild. And I went to her house in Montecito near Santa Barbara and you know like I was brought to this little like guest house which is you know like nicer than any of our houses but it's like you know and I'm like they do hair and makeup on me and they get me all ready to see Oprah and because we're shooting this show she's interviewing me on the show and you know it's this big kind of moment.

Like, I'm like, okay, I'm going to meet Oprah Winfrey. And they tell me to go down this path through this like redwood trees. And at the end of this path, there's Oprah. It's like getting married. I know, I know. I walked on this little rocky thing. And then it's like, oh, she's like, Cheryl, you know, and she hugs me. And we sit down at this table. And the thing that struck me, and I was like, this is Oprah's, this is why Oprah is successful, is that she, the look on her face and what I could see in her eyes is her vulnerability. That I was meeting Oprah, and I wanted her to like me, and Oprah was meeting me, and she wanted me to like

her. It wasn't like meeting the queen, even though for the record, she is a queen, but she didn't act like one. Like she never, like she was still like this incredibly humble human who was really looking to have an authentic interaction with me. And I thought, you know, this is what has driven her success, is that it wasn't, you know, like the thing that makes her get up and do that work that she does every day is that genuine desire to connect with people and be vulnerable and to be open to what's going to happen next. And that kind of curiosity has driven her, you know, to these great heights.

And I think that, you know, some people, they forget that. Like, they forget that thing that got them to where they are, right? And to me, the mark of success is staying open in that whole way. You know, and Reese Witherspoon has also done that. You know, so when I had that first conversation with Reese, and my first question to her was, why, you know, why does wild matter to you? Like, what did, why, you know, because she said, I read it and I cried and I was like, why? What happened in your life that made you feel these, you know, that made you respond the

way you did to the book? And she told me. And she told me things within five minutes of talking to her that she's never told the world. And I trusted that well this this is a conversation that I would love to continue for hours but we're coming up on time and perhaps this is a good point to ask is there any suggestion ask that you have for the people listening,

anything you'd like them to consider doing, ask themselves or otherwise? Well, I think I should give them all a writing assignment, don't you think? Perfect. Yes, I do. I do think. I think one of the prompts in your book, The Tools of Titans, you did this list of writing prompts. You mentioned the darkest teacher one. Do you have a favorite one from that list?

That was my favorite. Yeah. Because it immediately put me on my heels and made me think about the juxtaposition of darkest and framing it as teacher. So yeah, your darkest teacher is, and so that's the question I would have for your listeners and people in the room if you feel like going home and doing a writing assignment. Write about your darkest teacher. And that is to say a person in your life who taught you something you didn't want to know about humanity or the world or yourself. And so often, you know, those people have hurt us by teaching us those things, and so

we just, like, push them away, and we put them over there. And then we never actually get to learn what ends up always being a valuable lesson from them. And for me, so much of writing about, like in my case, it's my father. I've written about him in ways, and I couldn't really write about him until I sort of worked my way to that place that I understood him as a teacher. And when you understand that somebody is your teacher, that you can't help but feel, like I said earlier, a little grateful for them, a little grateful for even the thing that you got from them that you didn't want to have. So do that. That is a great assignment. Thank you for being here, Cheryl. Thank you all. Ladies and gentlemen, Cheryl Strayed. Thank you. Thank you.

Hey guys, this is Tim again. Just a few more things before you take off. Number one, this is Five Bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that,

check it out. Just go to 4hourworkweek.com. That's 4hourworkweek.com all spelled out and just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it. This episode is brought to you by MeUndies, which I'm wearing right now. I've spent the last year or so

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MeUndies.com forward slash Tim. You can see some of my favorite underwear. And also plenty for the ladies. That's meetundies.com. This episode is brought to you by ID Commerce and Logistics. I'm asked all the time about how to scale businesses quickly. Rule number one is removing unnecessary bottlenecks that are a headache and also an emergency break on growth. For many companies, one of the first things they should outsource is inventory management and fulfillment. There are companies that do this all day long perfectly for fast-growing companies. ID Commerce and Logistics is one such company. They focus on helping online retailers and entrepreneurs outgrow the competition by handling all types of logistics

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