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10 mins

Cheryl Strayed: Listen For The Truth – Transcript

Read the transcript of Caitlin's interview with bestselling author and advice columnist, Cheryl Strayed.
by Natallia Darozhkina | Aug 23 2018

Caitlin Schiller: Welcome back to Simplify! I’m Caitlin Schiller…

Ben Schuman-Stoler: And I’m Ben Schuman-Stoler. It’s good to be back in the studio with you together!

Caitlin: With you! Hi! It’s great to be back. And with this episode of Simplify, we kick off Season 4 of the show – a whole year of Simplify under our belts.

Ben: Yeah. It’s been pretty incredible. I mean, I don’t think when we started a year ago now-ish, I don’t think we would have thought we put together four seasons.

Caitlin: No way. It seems like it’s been way more than a year or two actually.

Ben: Yeah, and it’d be interesting to hear what people out there remember from the beginning.

Caitlin: Sure.

Ben: We’ve had some really cool conversations.

Caitlin: Yeah. And the one that we’re about to hear today is among my favorites.

Ben: Yeah, I mean, in the tradition of Simplify seasons’ first episodes, episode 1s – I mean, we had Seth Godin, we had some big names – I think, Cheryl Strayed fits in there perfectly. How would you describe her, like just writer?

Caitlin: Yeah. She’s a writer, but one of her specialties is advice, but she has a lot of breadth. After all she is the person who wrote Wild that blockbuster memoir that became a film starring. Who was it?

Ben: I think, Reese Witherspoon.

Caitlin: Yeah, right. It was Reese Witherspoon. And it was huge. So one of the things that she’s best known for is this advice column called Dear Sugar.

Ben: Yeah, and I remember hearing about Dear Sugar. And I remember like someone would send to me an article or I would end up there, I wasn’t like a regular reader. But Dear Sugar was like – and is – a podcast now, the podcast with the New York Times. It was like this institution, it was like a place where people would read consistently, all the time, go back, and they really loved Strayed’s voice, and they still do. I mean, she’s got this amazing following, which she says she built because of like a sort of earnestness and authenticity. And I love that.

So, cool, all right, let’s play the tape. For new people out there – hello and welcome! And also stick around after the interview because we’ll make a list, Caitlin and I talk books, we make a booklist based on what the episode is about. So we’ll catch you after the tape.

Caitlin: Yep, sounds good.

Caitlin interviews Cheryl Strayed

Caitlin: Hi Cheryl! Thanks so much for coming on today. Could you please introduce yourself the way that you like to be described?

Cheryl Strayed: Hi Caitlin. It’s great to be on! The words I would use to describe myself: writer, feminist, mother, traveler, sugar.

Caitlin: Sugar, right? So let’s jump into that. You are the “Sugar” of Dear Sugar – the advice column. Can you tell me about becoming “Sugar”?

Cheryl: So it was early 2010, and I had just finished writing the first draft of my memoir Wild, and I sent it off to my editor and I was waiting for her comments, and feedback, and so forth. So there was this wonderful and exhausted feeling of having come to the at least the first end of that big undertaking of writing that book, but also that sense of like, “OK, what next?”

And right into that moment of my life, I got that email from my friend, the writer Steve Almond. And he wasn’t really my friend then, I had met him at a writers’ conference and I was a fan of his work. But I got this email and he said, “Hey, I’ve been writing this column called Dear Sugar for this website called The Rumpus, and nobody’s reading it, and I’m not really into writing it, and it doesn’t pay anything. But do you want to take over the call?

Caitlin: What an offer!

Cheryl: I know. It’s like, how could I resist? But really, how could I resist? Because immediately I thought, “Wow, you know this would be such a fun thing to get to read other people’s, you know, anonymous letters really asking for advice about their struggles, and their sorrows, and their problems.” And, you know, I’ve always been like most writers and most people really – but especially most writers – deeply deeply curious about the inner lives of other people. And so I said yes, even though it didn’t make any sense at all. And so many people – I was in a writers’ group at the time, and they all said, “No, that’s a bad idea. You know, you’ve got to be paid for your writing and you’re busy with Wild.” And I had my kids were really little at the time, you know, they were like, quite young, you know, three and four, four and five or something. So I had enough things on my hands.

So what happened is when you’re not being paid anything to do something, you could do whatever you want, which is beautiful. So I started writing that column, and what happened is, I decided… First of all, I was not a connoisseur of advice columns at that point. But I just decided that I was going to not pay any attention to HOW you’re supposed to do an advice column, and instead really make these letters my replies literary essays about living. And so I did that, and I really told stories from my own life, and I told stories about people I knew, or books I’d read. And you know, I went sort of full throttle when it came to trying to address people’s problems, and not in the way of telling them what to do so much as trying to illuminate and deepen the questions they were asking.

Caitlin: One specific letter that’s in Tiny Beautiful Things. I think, it’s entitled too much paint. And you talk to someone who identifies herself as “man juggler,” who’s seeing, I think, two or three men at once and she’s feeling totally overwhelmed by it. And her letter spoke to me about this condition of FOMO, and about feeling like you have to have things just for the sake of having things. And she was juggling these men because she could. And what you told her is that “the beauty of her position is that she doesn’t have to juggle, instead she can give it a break and inspect the negative space.” Can you talk about the negative space a little bit and why it matters?

Cheryl: Yeah, I think that that to me… I’m 49, and I’m going to be 50 in September, and I have always loved getting older. I’ve never been one to freak out, when I’m turning 30 or 40 or 50. I always greet that with a sense of joy. And I think, it’s because I really deeply value the things I learn as I get older. And that advice that I gave her is something that took me a long time to learn. And I think, it’s something that a lot of 20 and 30-somethings struggle with, is that that sense of, you know, essentially what man juggler was doing is making her own problems. So, she was essentially saying like, “Oh my God, I’m so freaked out. I’m sleeping with all these different guys, and I just don’t even know what to think about that.” And, you know, “Help me.”

Caitlin: Yeah, and she said she felt overwhelmed. It was just too much.

Cheryl: Yeah. So what’s funny about that is like, OK, you know, attention to self, you know, you’re the one who’s sleeping with all those guys. So, it wasn’t as if… Like, she had the cure, like, all she had to do was say, “Oh, you know what? It makes me feel overwhelmed to sleep with too many people. I’m not going to do that anymore. I’m going to recognize that I don’t like that feeling. So I’ll stop creating that feeling by making these choices.” And you know, that advice I gave her about honoring the blank space, that what I said is, you know, in art, you know, the places on the canvas that the painter leaves blank are as important as the places on the canvas where we put the paint. And that’s also true in our lives, right. That for her, in so many ways that decision that she was making, which I don’t think she was making very consciously to, you know, go from one man to the next, was really about covering up her own blank spaces so that she couldn’t actually see herself clearly. Bullying her life with other people, because she was afraid of what she might see, if she sat alone for a bit and stared at that blank space within herself.

You know, but that’s what the beauty is. With age you come to see that even though there’s that temporary boost of like that next guy who wants to get down with you, it’s a false rise. You know, that deeper sense of glory is about, you know, making good decisions for yourself, and being able to sometimes be the person who meets your own needs rather than relying on others to do that all the time. You know, so that’s essentially what I was saying is that you have to give yourself, make that scary leap in the direction of silence, and not reaching out to other people, and not filling that void with somebody who’s going to flatter you temporarily but make you feel lost and alone later.

Caitlin: Yeah, so much of what you do is actually listen. Ursula K. Le Guin says that “listening isn’t a reaction, it’s a connection. And listening to a conversation or a story, we don’t so much respond, we join in and we become part of the action.” And you really do that in Dear Sugar. Does it make you tired?

Cheryl: Well, it’s deep work, that’s for sure. And I want to say first, you know, I think that that’s absolutely it, and I think, listening is so vastly misunderstood. Because of that, we do think of listening as in some ways waiting for the other person to finish talking, and that’s so incorrect.

And I think, what happened with Sugar, you know, my writing of Sugar in that column is because I would often respond with a story about my own life, what I was trying to do was, you know, make a thread, a thread of connection between my life and the letter writer’s life. And then what would happen is, you know, when the column’s really connected with people is they would find the thread that connects them to me and the letter writer as well.

So, you know, somebody might say, “Listen, I’ve never had a miscarriage, but oh my goodness, that letter that, you know, from the woman who had the miscarriage and then your reply spoke to me so deeply.” Because, of course, we weren’t talking about a miscarriage. We WERE talking about a miscarriage, we were also talking about deep loss, and what do you do when you feel misunderstood by the people around you, or you feel alone or isolated. That’s always been the thing I’ve been most interested in as an advice giver, is that again, I keep using these words like, “illuminate” and “going underneath”, and the questions that lurk beneath the questions we think we have. That’s to me, what I was always listening for, and trying to connect not just myself to the letter writer, but really frankly the letter writer to his or her own feelings and own language. I often would say, “You said this thing, so it’s not me telling you this is true. It’s you told me it’s true, but you’re not listening to yourself, which is a really deep fascinating piece of this.” And I do it too, you do it – I don’t even know you, but I bet you do it.

Caitlin: All the time!

Cheryl: All the time!

Caitlin: Even after four years of therapy.

Cheryl: Yeah, I know. And that’s what therapy is for, is really just nobody’s ever going to cure you if you’re suffering. Nobody’s going to solve every problem you have. But the endeavor, you know, when we do try to do that, what we’re doing is trying to more accurately hear our own inner voices.

Caitlin: What do you think that a person needs to have in place sort of spiritually within themselves to be able to give good advice? If you think back to people that YOU go to for advice or people you really trust with your stories and your torments, what do those people have in common?

Cheryl: That’s a great question. I think, listening is a big one, and a lot of people don’t know how to listen. You know, listening for a sense of connection and understanding, rather than listening to think, “Well, what do I have to say in response?” But really just understanding where that person is coming from. And I think, part of that too is being inquisitive. One thing I find a lot is that when I seek advice, when it works out the best is when I can find a friend who will then ask me more and more questions. So he or she has a deeper understanding even of what I’m saying. I think that’s incredibly helpful.

So I think that that kind of listening and inquisitiveness. I think, also this phrase I use a lot in my work as Sugar: “unconditional positive regard.” Listening while withholding judgment, listening with a sense that no matter what you tell me, I’m not going to be repulsed or astonished, or upset with you for having expressed that feeling or that thought. And that’s a tricky one, because of course we all have opinions about the things that people tell us—I do too. But at least for the duration of that exchange, in which the person is seeking advice, that you can try to the best of your abilities to withhold your judgment and to not make that part of your listening or your response.

Caitlin: Yeah, it really feels like on the podcast and your books like you do have unconditional positive regard for all the people whose questions you answer. And I wondered if that was because of editing, as in you selected to whom you would respond? Because I can’t imagine you like everyone who comes to you. What do you do in order to steel yourself for these encounters or you have to get really into it with someone whose insides you might not totally adore?

Cheryl: Right, right. Well, it’s made easier by the fact that the only piece I see of them is that letter that they wrote to me. You’re right that part of it has to do with the letter selection. If I feel like I’m not going to be able to respond to them with compassion, I don’t. And this is true even in cases when I do feel like the letter writer has something to learn. You know, it’s not that I’m always incredibly supportive and loving. I mean, I am! I think I’m incredibly supportive and loving to every letter writer, but I guess, what I need to say is that it doesn’t always equal that I tell them everything they’re doing is great, and they should just keep doing what they’re doing, and it’s all going to be OK. Sometimes I’ll challenge them and say, “Yeah, it’s not all that at all.” Sometimes I’d really kind of school people, right? And yet, it’s always done with the sense of unconditional positive regard, a sense of love. And for me, I don’t know, I’ve always been… Compassion is pretty easy for me to feel other people’s sorrow, and to understand that that sorrow or that wound comes from someplace real. I believe in everyone’s capacity to be better, to heal, to confront the things that are hard to confront. And so, you know, I focus on that and that allows me to kind of keep my judgment out of it.

Caitlin: I so much identify with what you just said. Even as as someone who conduct interviews with people, who sometimes have kind of problematic ideas. I find myself, it’s really hard for me not to come to a place where I find something redeeming and interesting what they have to say. And usually by the end of the interview, I’m like, “I don’t know, this person is actually alright.” It’s hard when you spend time with someone, and their ideas, and their actual real-time expression, to not find something that you can care for in them. I get it.

Cheryl: This is why literature matters. Because it’s really hard to hate somebody, once you know their story. It really is. And this is why it’s so powerful and important to me that, you know, when I say books saved my life, that’s what I mean is I saw myself in the pages of the books I read all my life, I found myself there. And when you find yourself what you’re really finding is all of us.


Caitlin: Hey, this is Caitlin. Just checking in to let you know that there has been a small change. You might have noticed on our cover artwork that it now says “Simplify by Blinkist.” This looks like a change, it’s not really because it’s always been made by Blinkist. And in case you didn’t know, Blinkist is a place where Ben and I work. It’s why we know about all these great books, it’s why we can talk to all these incredible authors.

And Blinkist is a learning app, it takes the insights from the world’s bestselling nonfiction, and it condenses them into little capsules of knowledge that you can listen to in audio or read in text in just 15 minutes or so. Even though this is a nominally branded podcast, even though that we are brought to you by Blinkist, we will never take payoffs to talk to an author. Ben and I choose who we talk to pretty carefully, and we don’t speak with them unless we’re super excited about their work, and think that there is something awesome in there that you would benefit from too.

So, anyway, you’ll see this new thing on our logo. It’s a change, but it’s not really a change. And Blinkist is the reason that we can make this awesome podcast for you. So, and if you want to try it, you can go do that. You can go to and type in the voucher code: sugar for this episode, and you’ll get 14 days free. That’s it, thanks!

Interview Contd.

Caitlin: I’m wondering: you’ve read so many letters, and heard so many questions from people who are in wondering about something. They don’t know where to go, or what to do next, or they’re in pain. Is there some sort of central struggle or a pattern in the pain that you pick up on, or a number of them? Are there certain things that you think, if we could just address this wound, it would be a little bit better?

Cheryl: Wow. Yeah, that’s such a… I mean, we could talk about this for hours, because indeed, of course…

Caitlin: Let me go grab the bottle of wine.

Cheryl: Exactly. Yeah, it’s late enough for where you are, that you can drink wine.

Caitlin: You can drink in Berlin at like 9 a.m, anyway…

Cheryl: Well, in Portland, Oregon too!

So let’s take this apart. OK, so the first one is, “Am I worthy of love?” And “Am I worthy of respect?” So, good love – love in which you are treated with kindness, and respect, and consideration. And it’s horrible and sad to me that so many people, you know, aren’t sure of that. It takes them years to believe that they are, that they are worthy of love, and they are worthy not just of any old love, but actually kind respectful good love.

And a piece of that is the patriarchy, frankly, a piece of that is gendered. I think, men struggle with this question too, but there’s something about a lot of female angst and anxiety is around. Basically straight females essentially saying, “Is a kind of ‘good enough guy’ good enough?” You know, even if he’s kind of emotionally abusive to me, or telling me I’m fat, or whatever it is, you know. And just to convince straight women that they shouldn’t be treated badly by their male partners is a big one. I mean, I think that there’s no way around the fact that it’s connected to the patriarchy. How could it not be? If so many of us, really all of us, you know, we’re all steeped in this culture that values essentially women attaching themselves to men. And in some ways, you know, that’s the kind of major achievement in a woman’s life. And so there’s that struggle.

The other one is, “Here’s who I really am and is that OK?” And that’s also one that, you know, who knows where any of this comes from? I mean, I have all kinds of theories. But a lot of people really feel like that they have to kind of pretend to be somebody else. You know, sometimes it is about the way they look, “I’m not good enough.” You know, we equate moral value with like, how beautiful you are, or how thin you are, or how fat you are, or, you know, any of these things. Sometimes it manifests itself in the professional life, like, “I really want to be a painter, but I’ve been pressured by my family, or society, or my culture to be…” – fill in the blank – something that’s a little more kind of normal and money earning, if you will. You know, so, “Am I OK at the way I am?” “Do I dare be who I am?” is a big question. “Am I worthy of love? Do I dare be who I am?”

The other one is “How do I carry this sorrow?” So many of us have experienced deep loss, you know, whether it be in the form of the death of a beloved person, a breakup that really hurts, or simply just the sorrow of like a past that was painful, a dysfunctional childhood, an addict parent, or you know, fill-in-the-blank any of those sorrows. How do I carry it? And we are a society that doesn’t teach people how to carry sorrow. We teach people how to try to forget about it, let it go, leave it in the past, move on – all that kind of stuff. But really moving on is not about shutting the door and walking away, it’s about learning how to carry that pain with some grace and with some light. And I don’t think as a culture we’ve been taught how to do that. I’ve tried really hard in my work to do that, to really address that question. I mean, that’s what Wild is all about.

Caitlin: I mean, I will not dare to ask you what the answer to that question is. I think that we can just refer people to any and all of your books.

Cheryl: Yeah, that’s right. But, you know, I mean, of course there are all these other things, but I think that that’s those three things – they cover a lot of ground, don’t you think?

Caitlin: Yeah, and they’re so interrelated, especially “How do I carry this sorrow?” I feel like that’s very related to “Do I dare to be who I am”, and “Do I deserve to be loved,” because we also are taught that we don’t deserve to be loved unless we’re happy and pleasant to be around all the time.

Cheryl: Yeah…

Caitlin: Which sucks, frankly.

Cheryl: It does, it does.

Caitlin: So, some of the work that you do as a writer in general, and especially in your role as Sugar, requires a lot of trust in yourself and in others’ goodness and others’ trust of you. What is at the center of that trust, do you think? What does it depend on?

Cheryl: I think, sincerity. That to me was really at the beginning, when I first began writing the Dear Sugar column is I knew that I wanted to, as I said, sort of give it my all and really make it literary essays. But also that I wasn’t going to be snarky, which I have to say, at the time, was not very common on the internet. My first fear, when I took over the column back in 2010, is that, you know, everyone was very snarky, and funny, and glib, and that was just very much the internet style. And I have always been very earnest and sincere. And I was afraid, I mean, I frankly thought that I was going to be devoured. And I was absolutely sure that people were going to reject the Dear Sugar column, at least my version of the Dear Sugar column, because I couldn’t be anything but sincere.

And what I found is that people were absolutely hungry for that. And of all the things that I’m kind of most proud about, in terms of like what I did with that column, is I do think that I was part of, you know, essentially being on a platform for sincerity online to say, “I’m not gonna make fun of you or mock you.” And what I realized is that very thing, that trust, is that people weren’t just writing to anyone, they were writing to me. And they trusted me. And I can’t tell you how many times people in their letters to me, I would edit this out, but they would say, “I don’t normally write to an advice columnist, but I trust you. Because I know that you will be kind to me, and that you’ll give me an answer with love, even if it’s something that’s hard to hear.”

And so yeah, you do build that trust, I think, by taking people seriously, and being kind to people, and all of the things that we do to build trust in real life – that’s what happens in that exchange as well, whether it be on the podcast or via letters. I mean, think about this, if you knew that an advice columnist or an advice podcast host was going to mock you and make fun of you, you know, you’d be a lot less likely to write to them, I think.

Caitlin: What is there, that practice you had as Sugar when you first started, and I think, you said it was 2010 that you wouldn’t do nowadays? Is there something that you’ve decided wasn’t a good practice and in your trade be “an advice industrial complex,” as Dan Savage would say?

Cheryl: Yeah, I shouldn’t have done it for no money. I should have never done that. Yeah, I mean, I did it… Nobody much was being paid at the Rumpus, but it is true that what happened is it became like this incredibly huge huge huge thing online. You know, every week it was like literally the website would crash because so many people were reading the column when it would go up.

And I think, it was fine to agree to do it for no money at the beginning, but then pretty quickly it had this huge cult following. And I think, I sort of regret that I let myself just be slightly taken advantage of in that way. You know, I love the people who made the Rumpus, and so I don’t mean this in a personal way. But I wish I’d stood up for myself and said, “Hey, you know, even if it’s just like a little bit of money is being made off of this, of my column, my labor.” And at the time, I was really really broke.

I mean, honestly, in the course of my 10-year writing that column on the Rumpus for which I was paid nothing, you know, my garbage was turned off, I lost my health insurance repeatedly because I couldn’t pay it on time, you know, the ship was really sinking. And I really should have said, “Even if you pay me 50 bucks a column, it certainly earning well more than that. And you know, I think, I should have stood up for myself better.

Caitlin: Yeah, absolutely. You get in there with your letter writers and you really keep them company in their emotions. And a lot of what you’re counseling to do is you said is to listen to them, and to get them to listen to themselves and trust their intuition. But in order to do that, you have to be very strong in your own. And how did you hone yours?

Cheryl: I really think that this kind of work is my calling. I feel like I was born curious about the emotional realm of our inner lives, and the truest version of ourselves and each other. I’ve always sought that. Like my earliest memories as a child were about that kind of curiosity. You know, when I hear scientists talk about how they became scientists, you know, they were always obsessed with the stars or they were obsessed with rocks, or you know, whatever it is. And I was always obsessed with people’s inner lives and our emotional lives, the ways that we love each other, the ways that we lose each other, and grieve each other, and long for each other – that’s my work, that’s my world.

And you know, of course that’s perfectly joined with writing because when you write, that’s what you’re always doing, right? You’re creating, at least in creative writing, whether it be in the form of memoir or fiction – and I write both – is that you’re essentially building a character on the page and inviting readers to live inside that character’s mind and body. And in order to make a credible character, you have to be not only willing to understand our humanity, but to always be seeking to do more, to dig into that deepest layer of truth.

When I teach writing, so much of it is about that. It’s essentially hard work. You know, when you think about what takes what it takes to be a writer, you know, there’s craft which is about learning how to construct a sentence, or a scene, or a story, or you know, write pretty words on the page. And I absolutely honor that, and I think that’s a powerful process of apprenticeship. And I also think that it takes this thing I’m talking about. You know, you could write a lot of really competent sentences and say nothing, if you’re not willing to really examine the soul, the spirit, and the heart.

And you know, is it draining? Is it exhausting? How did I get to be this way? You know, I would say that it’s not as exhausting as you think. I mean, that’s the question people always ask me, especially about my work with with Sugar – whether it be on the podcast or in the column. Because yeah, I’m always sort of wading into other people’s terrible situations and problems, and yet I’m there to help.

And I think, that there’s something about acting, responding, that is always inherently empowering. It’s like being at the scene of an accident. It’s harder to be the person standing by, watching someone bleed, than it is to press your T-shirt to that wound. And I’m the person pressing, you know, I’m trying to sort of be of service. And when you’re of service, you actually end up being absorbed and consumed, rather than devoured and exhausted.

Caitlin: If there’s an idea that you could leave everybody listening with today about really any of the things we’ve talked about today: intuition, trust, how to be a good advice giver. What is the central idea you’d like to leave them with?

Cheryl: Well, I think, intuition is a big one, and I don’t think, we’ve talked about it so deeply directly. And what that’s about, I think, a lot of people, you know, they kind of think they make intuition grander than it is. They think that it’s going to be some like big gigantic, you know, like lightning bolt realization you’re like, “This is the right thing, I know that.”

Very often, when I say things like, “trust your gut” or “listen to your body,” it isn’t that it’s such a strong strong strong sense of clarity and correctness. But rather that it’s that little tendril of truth that you feel inside yourself. And that you have to follow that, which of course makes it harder. You know, it’d be easier if it were like, “I know, this is absolutely the right thing.” I think, trusting yourself intuitively is actually about listening. And I love that definition that you shared from Ursula K. Le Guin, you know, that this is about connection. And that’s what I’m talking about when I say “trust your gut.” Connecting that feeling in your body to the action that you should take. Connecting yourself, you know, basically your mind to your heart. Your mind to your body. When you know, something isn’t right, it isn’t right.

And what I find in my advice giving, in my own life and my friendships is that the sooner you can listen to that inner voice, the better off not only are you going to be, but the people around you too. The people who sometimes we have to disappoint, or hurt, or say goodbye to, who frankly will be better off that we do it sooner rather than later.

Caitlin: Yeah. It’s a tough one. OK, and on a lighter note, I always like to ask people that I talk to for the podcast what they’ve been reading lately or what books they love and would recommend. I know that’s a huge question for you.

Cheryl: So many books! Well, I’ll tell you over the last year or so, a few memoirs that have been extraordinarily like powerful and beautiful, and I highly recommend to your listeners. The first is Educated by Tara Westover. Have you read that book?

Caitlin: No, but I’ve heard about it. But say more about it, I could use my memory jogged actually.

Cheryl: So, Educated by Tara Westover – a really interesting memoir about essentially her coming of age, and going from living in this rural, Idaho house with her family and essentially being, you know, kept from modern society. She didn’t even begin her formal education until she was like 17, and went to college, and the whole world opened up before her. Really an extraordinary book about about her journey.

And some favorites from the pile of books that are about to come out. My friend Courtenay Hameister is a Portland writer, an amazing person who used to be the host of a radio show called LiveWire! Her first memoir is about to come out at the end of July, and that’s called Okay Fine Whatever by Courtenay Hameister. It’s about her struggles with anxiety and essentially body image and, you know, all of the many many struggles many of us go through. And then she invented a few of her own as well. And it’s about her sort of year or so of trying to push herself out of her comfort zone in order to heal some of her wounds. Really really good book, really funny and also poignant.

Caitlin: Books are amazing. Anyway, OK…

Cheryl: I love books. I’m with you.

Caitlin: Cheryl, thank you so much for taking the time to talk today. It’s been such a delight!

Cheryl: Oh, it’s really wonderful to talk to you, Caitlin. Thank you so much for inviting me on to your show.

The Bookend

Ben: Welcome to the Bookend, where we end… with books. So, before we get into a book list, maybe we can talk about a couple of the main points in the interview. To start, why did you want to have Cheryl Strayed on Simplify?

Caitlin: Well, as I said, I wanted to talk to her about giving advice, and how you do that well, because I don’t think it’s actually that easy. But I wanted to talk with her specifically because she deals with the really sticky difficult parts of being a human being in a very brave deep way. Like, she writes about deep deep loss and grief, and how you can continue to move through the world with that. And that’s the thing that I think a lot of people aren’t familiar with discussing out in the open. And she really makes it OK, she makes it like a beautiful exercise in human connection. And I thought that that would be a nice element to bring into the podcast.

Ben: And so, what then should people take away from the discussion?

Caitlin: The main thing is really like how to listen, and the fact that listening is about connecting. It’s not about responding. It’s about really listening to the problem into the person who’s in front of you, and being tender with their very jagged vulnerable human parts. And it’s not as hard as it sounds, it just takes like concerted effort to not be formulating a response before they’re done talking, you know?

Ben: Sorry, I like that line, which is like, “Uh, right.” It was pretty good, it was live bad listening.

Caitlin: Oh, yeah. So that, so how listening is about connecting. And on that note, about those central vulnerabilities that connect us as human beings, that “Do I deserve good love? Am I OK as I am? And how do I deal with this grief? How do I deal with this loss?”

Ben: But what I wanted to say was…

Caitlin: Thanks for waiting, Ben! Yeah.

Ben: How good listening is not just waiting for your turn to talk.

Caitlin: Yep. You got it!

Ben: I got it!

Caitlin: So it looks like you could use some integration.

Ben: I’m glad that I just showed how bad of a listener I am in front of the whole world. But, you know, learning…

Caitlin: It’s OK, we all do it.

Ben: But I also think, there’s another thing she said about like relentless optimism, relentless positive regard.

Caitlin: Yeah, it was unconditional positive regard. That’s how she approaches all of the people who approached her with questions. So she’s determined to look at them with non-judgmental positive optimistic eyes. And I think, that’s really such a beautiful idea. Because how I think, related to just answering before somebody asks you a question, is assuming that you know their motivations, and what’s behind them – and that’s judging. But what she tries to do is just to make sure that she goes in there with a clean slate unconditional positive regard. Yeah, good that you picked up on that. Thanks for reminding me.

Ben: Yeah, and reminds me a little bit of from a different angle, we have two other really good communicators on Simplify.

Caitlin: Are you thinking – I just interrupted you…

Ben: No, but that’s different because I was going to say a fact.

Caitlin: Are you thinking of Stanier?

Ben: Yeah, right. Michael Bungay Stanier is a coach, and he’s sort of famous for these coaching questions. And the magic in that conversation you had with him was, he was like, people have no idea how powerful the question of “what else?” is there. Like you hear somebody out, and then you say, what else? I don’t know, I feel like, I think, I’m gonna try that this week. Just try to like hear someone out, and then, even if you feel like you get it, I’ve heard this before, just to be like, what else? I mean, he loves that there is definitely something there, but I feel like if we all tried that, I don’t know, it’s be pretty powerful.

Caitlin: Yeah, sounds good.

Ben: But let’s just move on to the books.

Caitlin: So should I start? I’ll start.

Ben: Yeah!

Caitlin: Good. All right. So this one is Nonviolent Communication by Marshall B. Rosenberg, and I recommend it all the time. I review it pretty frequently because I think that there are a lot of lessons in here that a person could use to review. And funny story, Marshall B. Rosenberg stayed at my good friend Amber’s grandparents house in New Mexico. And because her mom was into nonviolent communication, he just like came over to help her grandfather with some like issue he was having at work. And Amber remembers this moment, where she like looked into Marshall Rosenberg’s eyes, and she was like, “this person has DONE THEIR WORK.”

And his book is really really beautiful in earnest and gives these super practical tools for how to do that that non-judgmental thing with somebody that you’re talkin to you, how to really connect with them without assuming, you know more than you do, and without putting their hackles up. And how to move from imagining you know what the deal is to just making observations. Like, the phrase “My boss is always late,” that’s like a judging evaluation, whereas “My boss does not arrive before 8:30 a.m.” – it sounds a little bit robotic, but that’s more exact, and it’s an observation, it doesn’t have any like judgment attached to it.

Ben: And it also, it’s more likely to lead to some kind of solution. It’s something that you can actually adjust. You can’t say, “You’re always late” – now, we’re talking about like who you are as a person. But if I’m like, “You didn’t come before 8:30” – it starts to be like, “Yeah, because I never come before 8:30 because I work better at night. So we’re put in the afternoon.”

Caitlin: Right, it opens the door for “why.” And the other thing that nonviolent communication teaches – which I think is really amazing, and I’ve had to work on really really hard, and I think is really important – it’s how to be really really specific about your own needs and feelings, and how things make you feel rather than saying, “you made me feel X”, it’s formulated more like, “I feel X, when you Y.”

“I feel, you know, sad when you interrupt me”, not more like, “You interrupt me all the time, Ben!” Because then if I give you a way that I feel, you’re more likely to react to it, and be able to think about it, and it takes it on me rather than put all the blame on you.

Ben: Right. You interrupted me before I could make my point, and now I feel like I’m not as persuasive.

Caitlin: Yeah, like that. That’s really good. Also, apparently this all sounds really really earnest and touchy-feely, but also apparently Marshall B. Rosenberg had an amazing amazing wit, and he was super funny, and could just cut through all the crap in a room and make everybody laugh and feel at ease. So you can expect some of that too from this book.

Ben: I would also say, if we’ve whetted your appetite for nonviolent communication, just google it, there’s like workshops all over the world. It’s become like a movement, it’s not just a book. It’s a way.

Caitlin: Indeed. All right, I had another book, but I really like your picks. So why don’t you give your picks? I think, they’re kind of interesting.

Ben: OK, I have three books… Real quick, because the first two are in the more literary space. So, Walden by Henry David Thoreau and On the Road by Jack Kerouac.

Caitlin: Classics.

Ben: Have you read either them?

Caitlin: I have not read Walden, I have read passages from On the Road.

Ben: OK. These books have become almost like cliche, right? It’s almost embarrassing to be reading like with a big backpacker backpack alone on the train going somewhere, because it’s like, oh that person must be finding themselves. But anyone who’s read them, will remember the sort of click click BOOM that happens inside. I mean, these books are completely different style. Walden is like, you know, Henry David Thoreau stayed at a pond and just introspected himself for a while.

Caitlin: Wait, I want to go back to that thing that you just committed.

Ben: Click click boom?

Caitlin: Yeah. Did you have one of those moments?

Ben: Yeah. I mean for both of them, I think, there was something take-no-prisoner see what you see, and say what you see. And On the Road was about a sort of, for me it’s about an energy and a way to live. Something about being excited, something about being curious, being open. And the writing matches that. And that’s, I think, what excites so many 17-year-olds all over the world, as you read Kerouac and you’re like, “Oh, yeah, I just want to feel that possibility. I want to feel jazz. I want to feel the big city. I want to feel the girl. Or for someone – feel the guys. I want to feel…” You know what I mean? Whereas Walden is like, “Yeah, I also want to look at a pond for a year. And just be by myself.”

Anyway, it ties to straight, I feel like, in this earnestness. And she told you – this is a great moment, when you guys talk, when she says, when she started writing Dear Sugar, the sort of standard voice on the internet was snarky.

Caitlin: I remember that era.

Ben: Snarky critic. She didn’t do that. She was like, “I can’t do that. That’s not who I am, even if that’s what people expect.” So she was authentic, she did her voice. And that’s what people ended up loving, that’s what made her so big. And I think, the other thing that ties these books – I mean, these books are kind of classic American journeys – and I think, Wild, we might be talking about Wild like that, about American person in the wilderness feeling the country, feeling the space, going out and…

Caitlin: Reconnecting with herself and the world around her, and like finding out who that person actually is. And what strikes me is that what the undercurrent here – I mean, you’ve said truth-telling, you’ve said earnestness. But I also think that it’s a kind of intuition, that also shows up in Cheryl Strayed’s work: the ability to see what you see, and report on it, and to say, “Yeah, I want to go look at a pond,” or to say, “Yeah, I want to hike the Pacific Crest Trail,” and just do it to really be true to what your desires are, and follow through on them. Cool!

Ben: Yeah, and then the second book I have is maybe more closely related to Strayed precisely, which is The Art of Asking by Amanda Palmer. Did you ever listen to The Dresden Dolls? That’s the band that Amanda Palmer was in, kind of like an indie music legendary band, but she put out this book a few years ago, which became a New York Times bestseller, it’s called The Art of Asking. And Amanda Palmer is a person kind of like Strayed that has a huge following, and has a huge following because people love the way she handles the world around her somehow. Whether it’s a newsletter that she puts out, whether it’s a performance she gives, whether it’s about a blog post, or an interview.

What’s really amazing about the book is she doesn’t only say, it’s not only the story of like an artist finding their art, it’s about how she built a newsletter, it’s about how she figured out the right way to connect with people on the street as a street artist. And so that kind of balance of the artistic part, and then maybe slightly non-artistic part of growing as an artist, getting your work out there, finding people who will follow you, selling something. I think, the title – The Art of Asking – is an amazing hint at that, but I think, it connects to Cheryl Strayed’s tone and style of again, daring to be who I am. Like, I have a right.

Caitlin: I feel like you have a an obligation. That’s what we’re here to do: refine each other and just be ourselves.

Ben: Right, staying true. So, The Art of Asking is definitely worth picking up.

Caitlin: Cool. Those are great! Thanks, nice recs! I’m glad we got some literary recs in there this time, and some more practical ones too. So, I guess, that’s about it. That wraps up Episode 1 of Season 4. And I guess, thanks.

Ben: Yeah, cool. Those are the books. Today’s episode of Simplify was produced by me, Ben Schuman-Stoler, Caitlin Schiller, Nat Darozhkina, and Ben Jackson. Last time I talked to Ben Jackson, he was working on this idea about taking stuff learned from the gig economy but in face tattoos. I don’t know, it’s kind of a long story, but we’ll check up on that later this season may be.

Caitlin: OK, all I’ve got is a look of horror for you. All right, if you enjoyed this episode Simplify—send it to somebody like. You can find us on Apple podcast, you can find us on Spotify – all the places you find podcasts. If you’d like to talk to us, you can write to us at [email protected]. I’m on Twitter @caitlinschiller, and Ben you are?

Ben: @bsto.

Caitlin: Cool! And that’s it for us for now. We’ll talk to you soon!

Ben: Yeah, this is Ben checking out.

Caitlin: Checking out!

Read the show notes for this episode here!

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