Cheryl Strayed on Being Brave Enough to Break Your Own Heart

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2:29People stop believing that somebody's got your back or Superman's coming. We turn to ourselves and that's where you become empowered. Courageous participation attracts positive things. I'm Gwyneth Paltrow and this is the Goop Podcast, where we bring together visionaries, scientists, healers, artists, and seekers. I'm so grateful that I get to interview these extraordinary thought leaders and share their wisdom with you. and I love listening to the conversations that are led by my co-host and dear friend, Cleo Wade. Cleo is a beautiful poet and author. I deeply admire her and the way she keeps her heart open to the world.

3:12Together, we believe that engaging in open-minded, honest, and sometimes difficult conversations has the power to change our lives. All right, over to Cleo. Today, I had a really special guest come on the podcast. I got to sit down with Cheryl Strayed. The New York Times bestselling author of Wild, Brave Enough, Torch, and Tiny Beautiful Things, which is now a show on Hulu. We started our conversation talking about Dear Sugar, the beloved advice column that kind of started it all. I had a lot of questions for Cheryl. After all, she is the queen of good advice. We talked about parenting babies and teens.

3:53We talked about finding courage and doing really, really scary things. And we talked about vulnerability. Of course, Cheryl has so much wisdom to share about all she's learned in loss, connection, and self-forgiveness. So let's get right to this conversation with Cheryl Strait. Where are you now? Are you in Portland? I'm in Portland. I'm in my basement in Portland, hiding out from the chaos that is my life. and I am just, yeah, really excited and busy, busy, busy, busy, busy with the launch of this show, Tiny Beautiful Things. I want to talk about it. I'm so excited because I've been waiting for so long.

4:36I remember when you guys first started talking about it and working on it and the kind of all the different iterations in the creative process. And then when I found out that you were going to be in the writer's room, I mean, it was just, I don't know. I mean, I'm like a fan. Thank you. Cleo, that means everything to me. You know, I'm a fan of yours as well. And yeah, like so many paths worth walking. It's been a jagged and twisty one. And yet here we are, you know, at the mountaintop and what an experience it's been. It's really exciting. And you're right. I was in the writer's room, which was so fun.

5:11We had a zoom room, so I was able to join from Portland. What is it like for you? Cause I feel that we go through periods where we get to do a lot of stuff that's new for me. At least I go through long periods of time where I'm not trying anything new that's scary. And then when I do, I end up doing 30 things in a row that are scary, or I'm trying for the first time, or I wasn't sure I wanted to do it. And then I wanted to do it and I tried it. So what is it like, you know, you know, you know how to do what you do so well, because you're such an incredible, you know, memoirist and writer and advice giver and, and, and, and also you're writing seminars.

5:47I mean, what's really interesting that where my mind first went is that actually, you know, you said I'm a good advice giver, but, but you know, when I said yes to, to doing the Dear Sugar column, I had no experience writing an advice column and I wasn't even really much of a reader of advice columns. Like it wasn't like, oh yeah, this is like what I've been dreaming for all my life. I was, I was a writer. I write books, you know, that's what I do. My first book is a novel called Torch. My second book is a memoir called Wild. I had just finished writing Wild when I was asked to take over the Dear Sugar column.

6:23And, but when I say just finished writing Wild, I mean, I sent the first draft off to my editor. So I was like waiting to hear, like get notes, like you always do. And Steve Almond, who is my dear friend now, but he was really just an acquaintance at the time, we'd met at a writer's conference and we'd read each other's work. He emailed me and said, will you take over this column? It doesn't pay anything at all. And nobody reads it. And it's anonymous. I'll get no credit. And I was like, yeah, sign me up. And, you know, and I then immediately was like, I don't, I don't know what I'm doing. How could I possibly give advice?

7:01And, and, and what was cool about it is it was just exactly what you were saying, like that new scary thing. And I ended up finding my way along. And, you know, I think so much of my life, I wanted to say, I almost said career, but I think life is the better word for it. So much of my life, I don't, I don't, I can't separate my writing from my life. My writing is me. It's obviously a career too, but like so much of my career has been that kind of following the path where it leads me. After Wild was published, I began essentially an accidental career as a public speaker. Did you think that after Wild also, you would have, created this new iteration of speakers and in the self-help space, you were so different.

7:50And did you, did you expect that you would kind of have become a kind of self-help kind of go-to for people? It makes me feel like the people who do just have a really good picker for what is actually helpful, which is a really honest person who believes in love and all the things that come with it, like walking towards it, letting it go, creating boundaries. Yeah. And yet I also, I'm like grittier and more grounded. Let me tell you this, I was so surprised when Tiny Beautiful Things came out to find the book in the self-help section of bookstores. I was like, what? And same with Wild. But when I was writing Wild, it never occurred to me once that people would read it and be like, oh, I'm so inspired.

8:40Like I didn't think I was writing an inspiring I wasn't trying to make people feel a certain way. And that's been true all of my writing life. Like I've really tried to write from that place of deep truth that is gritty and grounded, that is honest and is very emotional. And I guess what that ends up being in the end is it feels transformative to people in a way that that can be. Yeah. Like I'm I had no idea that I would be at all categorized as self-help in any of those ways. But what's really interesting, too, is I want to say it really began with my first book, Torch, which is a novel. It's fiction.

9:21It's but yet it is also it is a story about grief. It's a story about family and relationships and being broken and not knowing how to find your way forward. And even just when that book was published, people would say, this really helped me. I understand. And so I think that it's not so much that I'm trying to write self-help as it is that I'm writing always about very emotional things that are very vulnerable and close to our hearts. And people experience that in a very personal way that feels like self-help. when I found out that you would so graciously do this podcast with me I took your book which actually I have an OG copy of it look at you I took your book two copies of it to the beach with two of my girlfriends for the day and and what I'm also really excited about I really want to talk more about the show that's coming out on Hulu in a couple days also but it's really cool that it's going to kind of be unleashed to an entirely new generation of people too which I'm so excited about because that is the really amazing thing about when things come to television.

10:30When was Tiny Beautiful Things published? It'll be 11 years in July since it was first published. That new copy is the 10th anniversary edition. But yeah, it'll be 11 years in July. The thing about Tiny Beautiful Things is kind of weird is that it was published just a few months after Wild. So I had two books come out basically back to back in 2012. And of course, Wild ended up being such a hurricane of an experience that, you know, Tiny Beautiful Things got a little overshadowed by it because it was like, you know, the book came out and people found their way to it. I'm not saying that's not the case, but it was just very strange to have two books come out so close together.

11:07Yeah. Well, my girlfriends and I were reading it and I was like, what do you feel it is? Because we were both saying that we were kind of crying in the midst of some of the advice you were giving and things that had truly nothing to do with anything we've ever gone through. And I was saying, I was like, and also, why do you think it works? Because also you, I would say, and this is very much my just personal opinion, but you kind of ushered in an entire kind of genre of ways that people write and do this thing. And it's actually really hard. And to do, I mean, I, even the first time I really even heard the term radical empathy was from your writing and how it could be kind of contextualized to today.

11:51And I think now we like kind of tiptoe into this place of like toxic positivity, which I think people try to call radical empathy. And I think that there's this kind of whole new genre of writers that were born out of your style of writing, to me anyway. But I was saying, I was like, why do you think that, like, how do you think that Cheryl just like, got it. Like, how do you, what do you think it is? And my friend said this really interesting thing. She was like, I think her ability to make all of the advice and offering and not a desire to control is what makes it actually so, even when you're reading the hard stuff, so nourishing.

12:34And I really thought that was such an amazing way to describe your style of writing. I think as a whole, even for Wild, I felt that it's also just, it was so, there were parts that were so hard in there and you really invited the reader into your pain and you do in Tiny Beautiful Things also, but you do it in a way where you're holding them. You don't allow them to almost fall into the bottomless pits we all have in her own kind of directions. And how do you find that you can walk that line so that you can kind of do the share without it being the overshare and navigate the trauma without it being the trauma bond or the trauma dumping.

13:22And because you're really, to me, one of the only writers who can write in this way. And it doesn't cross those lines for me, which I'm very sensitive to as a reader. Yeah. Well, I think I'm so honored by that word offering because I do think that that's what I do as sugar. And I still write the Dear Sugar column, by the way, I write it a monthly letter. Yeah. Yeah. And you know, and what I think of it is this in offering, meaning I'm not telling if I, in so many of the letters, I do tell a story from my own life that in some way connects either directly or indirectly to the, to the situation that's been presented to me in the letter that's been written.

14:04And I never am telling that story to say, oh, well, you know, you, you think you've got a bad, let me tell you about my story. You know how some people can do that and you feel diminished by it. And what I do is I really genuinely, genuinely believe in the power of story to illuminate the human condition. And so when I am telling a story from my life, it is an offering that is offered because I think it will help the person who's written to me see their own situation more clearly or more complexly. I also really always hold the letter writers in what I call unconditional positive regard. And to me, what that means at root is that I'm so not interested in judging you or condemning you or deciding that you've done a bad thing or a dumb thing, but rather I'm interested in speaking speaking very honestly to you with all the love in my heart and that I'm on your side and that I'm rooting for you and I'm in your corner.

15:07And I believe not only in you, but I believe that you have the capacity actually to answer all of your own questions. That my role isn't to tell you what to do, but to give you permission to know what you already know on your deepest level. Very often, it's that it's not the people are so you know bewildered it's that they're scared they're afraid yeah because it it's scary to know what you what you know because when you acknowledge what you know to be true you have to act on it you have to change your life you have to change your mind you have to say painful words out loud or or make decisions that scare you you know and my job is to take your hand and to say, you are not alone in this journey.

15:55We all have to travel this way if we are going to live evolved lives. And I'm, and I'm going to be here with you and not just, I'm going to be here with you, but like, we're all here holding you. And that to me is, you know, that's, that's the kind of work I do. Like, that's what, that's how I approach the work. and it does feel like an offering by the time. At the end of every column, I feel that way, like I'm holding out a platter that is, you know, everything I have to say about a situation that's been presented to me. I get so many headaches every month. It could be chronic migraine, 15 or more headache days a month, each lasting four hours or more.

16:37Botox, autobotulinum toxin A, prevents headaches in adults with chronic migraine. It's not for those who have 14 or fewer headache days a month. Prescription Botox is injected by your doctor. Effects of Botox may spread hours to weeks after injection causing serious symptoms. Allerge your doctor right away as difficulty swallowing, speaking, breathing, eye problems, or muscle weakness can be signs of a life-threatening condition. Patients with these conditions before injection are at highest risk. Side effects may include allergic reactions, neck and injection site pain, fatigue, and headache.

17:04Allergic reactions can include rash, welts, asthma symptoms, and dizziness. Don't receive Botox if there's a skin infection. Tell your doctor your medical history, muscle or nerve conditions, including ALS Lou Gehrig's disease, myasthenia gravis or Lambert-Eaton syndrome, and medications, including botulinum toxins, as these may increase the risk of serious side effects. Why wait? Ask your doctor. Visit BotoxChronicMigraine.com or call 1-800-44-BOTOX to learn more. You're so amazing at kind of capturing the yearning beneath the question, because often we're yearning for something and it manifests in a situation.

17:40It's easier to ask a question about the situation than do the kind of deep dive into the yearning. But I guess I wonder, one thing that really strikes me about the advice you give as dear sugar is that you have this incredible ability to just arrive at the courageous thing. you know it's like you have to leave you have to you know you have to you know those things that people are really it's so hard to do like you know you have to just you know thank them for what they were there for you have to and there's the place where that purgatory of maybe or like oh well like the that we kind of land in you you're very I think so great at asking to do the thing that would be the catalyst for the, that would give them all the goodness and the change that they would make in that moment.

18:29But how do you, is there a practice of how you landed there? Because so many of us just struggle with kind of like years of like, oh, maybe I should do this, or maybe I shouldn't. And are you good at doing that in your own life? Or you just are like, okay, it's clear to me, this is the change you have to make, and I'm just going to make it. So break off this thing or move towards this thing. And it's those types of movements in the world are really hard to do. They are hard. And that's right. And I never diminish that. Like, I think, however, that the harder thing by far is to live a life in which you're, you're confused and not happy.

19:08And you're looking for something that's never going to be there. So, you know, I think that, that one of the things I say in, in the title column, tiny, beautiful things, I have, I say you have to be brave enough to break your own heart. And what that does mean is like allowing yourself to be clear about certain things. Much to my surprise, one of the most well-read letters that I've written a shaker is called the truth that lives there. And it's, I actually answered three letters in this column, which I usually just answer one, but I chose three because I have so many letters that say essentially the same thing.

19:45It's from somebody who's in a relationship with somebody who they love and have all kinds of good things to say about that person, but they want to leave. They don't want to stay in that marriage or that relationship any longer. And yet they're tormented because they're so afraid that if they simply say this thing, I don't want to be here anymore. I love you, but I want to go. There'll be bad people or that they'll never find love again or whatever, all of those fears we have. Right. And so for me to say what I said essentially was wanting to leave is enough. You know, the way I landed on that, Cleo was my own life, my own agony, my own suffering, my own being married in my twenties and realizing pretty much immediately that even though I absolutely loved my ex-husband and he is a wonderful human.

20:33I didn't want to be married to him. And the hell I put myself through because I couldn't let that one truth be true. And also the hell I put him through, you know, I had to come up with a reason that we had to break up. So I cheated on him. I regret that so much to this day. And all of that could have been prevented if I had just said, I love you. And I shouldn't have gotten married to you because or anyone, right? And like, that's just one example. The other is, I think, you know, we, we, we buy into these narratives. Like there's a letter, the ghost ship that didn't carry us. A man wrote to me saying, I don't know, you know, if I should be a father or not, I'm almost 40.

21:14Should I have a child or not? And I don't have any clarity around that. And what I said to him is essentially, you're probably not going to have clarity. What you're going to have is a decision and a life based on that decision. You know, you're going to either decide, even though I'm not sure, I think I do want to be a dad and we'll see how that goes. Or even though I'm not sure and I think I don't want to be a dad and we'll see how that goes. You have two different, you have to make a choice knowing that there's not going to be some big magic bunny that, you know, hops up to you and says, here's exactly what you must do.

21:49Like so much of life is staying open to, I guess, our own bewilderment, you know, and to get clear about something else. And that is that you will love the life that you choose. And these are things I think that when I say I try to answer the questions that sit beneath the questions that are asked to me, that's what I, you know, I try to dig into that deeper territory in my answers. And I feel that so many people have found such profound healing and being able to connect with the ways in which you listen and then reflect back in those, in your advice. And I guess I wonder in this world that I feel like we live in a world of a lot of communication and very little connection.

22:36And so in that, you know, there's we're communicating all day long as in these things kind of fly at us from through our phones on the Internet and email and there's nonstop communication. But I think people feel lonelier than they've ever felt and really disconnected from one another. And I feel that we're really kind of trying to find our way back, especially post pandemic. Do you feel that you're able to connect rather than just then purely communicate online? How are you finding that for yourself? And I guess also, what advice would you have for others and kind of this time that I think is a really weird time?

23:15It's really weird out there. Yeah, it is. And being online and social media, it makes that all more complex, you know, and to me, here's what I figured out, at least so far, is, you know, I think that what we see happening online are two things that sometimes at face value seem like the same thing, but they're actually opposites. One of them is connection, that you actually connect with people, you know, online. Dear Sugar exists because, you know, really it was the internet that made Dear Sugar. It was, I was writing that column anonymously as an online advice column. And the way it grew its cult following is people said, you have to read this.

23:58And it was about connection. It was about telling the truth about what it means to be human, being vulnerable, taking risks, you know, all speaking into those deep places. Right. And yet also what we see is sometimes what can seem like connection is really just a performance or an image or a presentation of an emotion rather than the emotion. And, you know, I think life is that way too, right? You go to a party and you're there in the room with some people who are posing and some people who are over in the corner, you know, crying and telling you about their divorce. And I don't know who you want to be with at that party, but I'll always be in the corner with the person who's saying the real thing.

24:42And so, you know, I think that that's true wherever we go. And, and for me, like if you were to say like, what, you know, what advice do you have for me? I want to connect more. I want to feel like that authentic sense of, of unity with others. I mean, it's such an easy thing and sometimes so hard to do. Just be vulnerable. Tell the truth about who you are and what you're feeling. Take the risk, you know, take the risk of saying like that one sentence that maybe makes your heart beat a little faster because it's the true thing rather than the thing that seems cool or interesting or like some sort of image that you want to put out.

25:19I'm so glad that you defined vulnerability in your definition after you said it and said, tell the truth about who you are and how you're feeling because vulnerability like self-care or all these other words that have become really popular culturally over the past 10 years, they start to mean a lot of different things. It's kind of how bell hooks encouraged us to define love, to say, what are your principles around love? So that when you say it, you know what you're saying and you know what you mean. And I think a lot of the time I hesitate to use the word vulnerability because it really is meaning a lot of different things to a lot of different people right now.

26:02Yeah. It can be performative. You're right. I mean, and I mean, that's right. I know. Self-care too. I mean, I, I, I get really leery about that term too, even though I know what it means. Sometimes it can be like, well, self-care is just for a certain like class economic class of people who can afford to get like expensive spa treatments. And, you know, I think, you know, self-care, I mean, I, my long hike on the PCT, which physically hurt more than anything was the greatest self-care I ever did. You know, self-care is not just, you know, luxury and listening to soothing music in a place that's, you know, smells like lavender.

26:42It can be that, but it, but I think real self-care is, is exactly what it says. Like, you know, doing what you need to do, taking care of yourself. It can be, you know, any number of things that don't like, it could be saying, you know, I feel good when I, when I bake, you go make a cake that's self-care or taking a walk like I do every day. Yeah. I think it can have the lightness or the depth that you need. And I think for so many, and I've definitely felt this in my own life, that it's self-care has been reckonings I've had, you know, self-care has looked like really working through or processing something that was, you know, really hard and difficult.

27:25And, and, and, and it was unpleasant the whole time. And I was uncomfortable from start to finish. I wrote once, if self love says, I love you, self care says, show me. It's just that you, you show yourself love. And, and as we know, love is always good, as in there's goodness woven and wrapped around it, but it, it is looks very different. And it can be an angry kind of roar and it can be this kind of gentle lullaby and it can be everything in between and manifest in all these different ways. And then I think self-care is also kind of can be that way. Yeah, absolutely. I love that definition.