Cheryl Strayed Tells Us What the Hell to Do Next
April 11, 2023
Glennon Doyle:
Cheryl Strayed is back. Cheryl Strayed is the author of the number one New York Times bestseller, Wild: From Lost to Found on the Pacific Crest Trail, which has sold more than 4 million copies worldwide and was made into an Oscar nominated film starring Reese Witherspoon, her bestselling collection of, Dear Sugar Columns, Tiny Beautiful Things, one of my favorites, was adapted for a newly released television show starring Kathryn Hahn and is available now for streaming on Hulu. Straight is also the author of the critically acclaimed novel Torch and the bestselling collection, Brave Enough. She lives in Portland, Oregon. And if you have not listened to our first episodes with Cheryl, they were amazing. So go back and check out episodes 118 and one 119.
Cheryl Strayed:
I love you so much, you know this, and I’m now even more obsessed and I have to say, Amanda, one of my favorite episodes is the All about Amanda episode.
Glennon Doyle:
Did you relate to that one, Cheryl?
Cheryl Strayed:
I did. Well, namely because I have spent my life as a flirt too. But no, I have to say I’m reformed and I’m more like Abby now, because you can only play with fire for so long, kids, without getting burned.
Amanda Doyle:
This is a follow-up episode I need to have with you.
Cheryl Strayed:
No. What Abby said, I was like, “Oh, I so relate to that,” that idea of here we are launching into this flirtation thing. I’m sure that’s not what you guys wanted to talk about right off the bat.
Amanda Doyle:
Yeah, it is.
Glennon Doyle:
We love it.
Amanda Doyle:
It’s what I want to talk about Cheryl.
Cheryl Strayed:
But what Abby was saying was like you realized like, okay, you’ve got to flirt responsibly. The energy, people misinterpret it.
Glennon Doyle:
That’s right. Flirt-
Cheryl Strayed:
That’s right.
Glennon Doyle:
… responsibly. I feel like that’s kind of like drink responsibly.
Amanda Doyle:
Some of us can, some of us never can again.
Cheryl Strayed:
That’s true.
Amanda Doyle:
That’s right.
Glennon Doyle:
So mad at everyone who can drink responsibly. If I were not an alcoholic, Cheryl, I would drink every damn day.
Cheryl Strayed:
My joke used to be I’m so glad that I’m not an alcoholic, because I love to drink. I’ve been on an alcohol journey over the last year actually, because I am somebody who can drink responsibly and loves to drink. But also I did start to realize, you know what? This isn’t good for me. This isn’t healthy either. All of that stuff. So I’ve really just got on a personal journey of drinking less and hardly at all anymore.
Glennon Doyle:
Really?
Amanda Doyle:
When you say not healthy for you, in what ways was it impacting you that you’re like, mm-mm, this is not good?
Cheryl Strayed:
I actually answered this letter in my most recent Dear Sugar Column. I do once a month on Substack letter, and essentially what happened is I realized I was starting to get letters from people who were saying, “Listen, I don’t have a drinking problem. I’m not an alcoholic.” But this letter writer I answered to, she said, “I tried to do dry January in support of my friend who does have a problem with drinking. And what I found is I couldn’t stop drinking. I kept saying I wouldn’t drink and then I would just pour myself a drink at the end of the day.” And I answered her letter, because I felt like this was reflective of the awakening I’ve had over this last year or so. And I know that there are so many people out there… I call it, who have a problem without a problem.
Cheryl Strayed:
There’s this weird binary that we’ve fallen into in this culture, where it’s like the alcoholics are the people who have a problem and everyone else just gets to drink their heads off every day. And I realized that that was false. And last summer I got COVID, I was in Greece, I got COVID, I was sick. It was like a nightmare. But when I recovered, I had that experience that I often have after a time of struggle, is I felt awake and aware and I wrote a letter to myself, it’s very Liz Gilbert of me. And I sat there in Corfu in the Syrian heat, and I just wrote this letter, “Dear Cheryl, here’s what you need to do to take better care of yourself. Here’s what you’ve known for ages.” And I wrote all kinds of things that I knew. And surprisingly, one of the things I wrote is you need to drink less.
Cheryl Strayed:
Because what was happening is, even though I never got drunk, even though I didn’t all of the bad consequences of alcohol, I was drinking pretty much every day. I was drinking pretty much two or three glasses every day of wine, which is like triple what is recommended by the CDC. And I wanted to deny… I wanted to say, well, I’m a moderate drinker, because I think by most people’s assessment I am and was, but by all the doctors and people who know about this stuff say no, that’s actually not moderate at all. So I started to just be mindful about that and to pay attention to how I was using alcohol and why. And I slowly but surely have pretty much stopped drinking.
Amanda Doyle:
I’m so thankful you said that, because I do feel like we have this polarization, where it’s either if you don’t have a DUI and you haven’t been arrested and your family is still together, then surely you can’t have a problem with alcohol. There’s this bucket and you almost need a justification. If you go out in the world and you’re not drinking, it’s like whoa, whoa, whoa. You can’t just elect to not do that. You have to have a demonstrated history of a problem to do something that aggressive to the world.
Cheryl Strayed:
Absolutely. A lot of stuff that a lot of us wake up to and realize, wait a minute, we’ve been fed this false binary that it’s like you’re either this or that. You’re good or bad, you’re an alcoholic or you’re fine. Whatever it is, almost always that binary is a false narrative. And if you can bring mindfulness, I feel like obviously there are lots of people out there who are like, “No, I can’t drink again, because it was a destructive force in my life.”
Cheryl Strayed:
But I’m not one of those people. I don’t have a list of things that I could say, this is what alcohol ruined for me. But what I do know is that it was slowly kind of silently probably ruining my health, that it is better. I do enjoy having a clearer mind and waking up in the morning not feeling that little tiny, teeny, eenie, beanie hangover, all of that stuff. And so I just think that there’s so much conversation right now about mindful drinking and sober curious, and that whole category of drinkers who would do well to think more mindfully about their drinking, even if they’re not going to completely give it up.
Glennon Doyle:
Holly Whitaker does a beautiful job in her book, Quit Like a Woman, talking about how big alcohol is the one that even put out the idea drink responsibly, because actually what does that mean? They created this idea that there’s a group of people that alcohol is bad for and you can find them in AA meetings, and then the rest of the world alcohol is good for. But actually instead of asking ourselves, do I have a problem, we could always ask, is this benefiting me in my life? Is it helpful for me to be drinking alcohol? And one of the things I always think about is most tragic about all of the things we do to take the edge off. I get taking the edge off, it’s probably why I go to bed at 7:30.
Amanda Doyle:
That’s when the edge really emerges. So she’s like, “Goodnight, moon, I’m out.”
Glennon Doyle:
But I know I’ve said this before, but I think it’s so important to me. It’s the edge that discomfort or that little bit of suffering that we take off with the booze or the shopping or whatever, that discomfort is usually that what propels us to change what this suffering that makes us make changes in our life. We’re like, “Oh, this friendship sucks and I can’t…” And then we just drink it away.
Glennon Doyle:
“Oh, I need to switch jobs. I can’t stand my job.” And then we kind of drink the edge away, but the edge of discomfort is there so that we won’t stay in discomfort so that we will move, so that we will change so that we will make the hard decision. So I always think of it in terms of the edge is there for a reason. It’s a gift to you to point you in one direction or not. And when we doll that edge forever, we just stay in the…
Cheryl Strayed:
Yeah, absolutely. And I think too, that there are healthy ways of dulling that edge. One of them is asleep, one of them is going to bed at seven 30 instead of having a drink, or going for a walk, or calling someone you care about. And I know, Glennon, you’re against phone calls, but connecting, texting. And for me what I realized, because that was the thing, when I decided in Corfu I had to drink less, my feeling wasn’t like, yes, I can do this. My feeling was like, I can’t, because that’s what I do every night. When the day is over and I’m cooking dinner or whatever, that’s my glass of wine. That’s my treat for myself. I give so much to so many people. Can’t I give myself anything? And I was almost mad that I was going to have to surrender this, but here’s what happened.
Cheryl Strayed:
It ended up being much easier than I thought it would be, because once I just decided, Cheryl, you can keep giving yourself something at day’s end, it just isn’t going to be alcohol. I replaced it with other stuff, because there are really cool ways to take the edge off, some of the things I listed, but I had a bad habit and we can change our bad habits.
Cheryl Strayed:
And now I don’t know what my drinking life ahead is going to be. I’m still sort of exploring. But one of the ideas I’ve latched onto is maybe I drink alcohol as often as maybe I eat birthday cake. But it’s like every once in a blue moon I will have a glass or two of wine, with the regularity I might have a piece of birthday cake.
Abby Wambach:
I love that. And when I think about alcohol, I’ve been sober almost seven years now. It’s like the human body is our processing vessels. So if we are poisoning it, because whether we want to admit this or not, alcohol is poison. And if we do that, we are not giving ourselves the ability to be fully human. I think about this so often in terms of creativity, in terms of planning podcasts, in terms of my business, in terms of my family, I need to be completely on all the time, so that nothing falls through the cracks. And I am so grateful every morning to wake up and to know that I have nothing that I have to worry about.
Glennon Doyle:
Oh God, yeah. Apologize for.
Abby Wambach:
Oh gosh.
Cheryl Strayed:
Oh my God.
Amanda Doyle:
And you still wake up after parties being like, what did I say… Oh my God. And then I’m like, wait, I don’t need to worry about that anymore.
Cheryl Strayed:
Yes. Well, at least most of the time, every once in a while I’ll say something really ridiculous, even though I’m stone-cold sober too.
Glennon Doyle:
Yeah, that’s the thing. We’re still ourselves, aren’t we? We’re still ourselves.
Amanda Doyle:
But it can be applied to everything. Cheryl what you just said is so important. The anger about being like I give to everyone else and this is the one thing. And so you’re saying not only do I need to keep giving to everyone else, now I can’t have my one thing? But that’s so true in our relationships. It’s true.
Amanda Doyle:
You can’t just take away alcohol. You can’t take away anything. You have to replace the thing that is meeting that need with something else that’s working better for you. And so don’t just take away. Say, “What am I going to add? What was missing that I was filling with this thing?” And give yourself the time and the money and the invitation to do that.
Cheryl Strayed:
Yeah, absolutely. And the permission to. For me, one of the things is I went on a journey of the non-alcoholic wine replacement beverages. So then let me just tell you, they all taste like apple cider vinegar.
Cheryl Strayed:
So I would pour my glass of apple cider vinegar and say to my husband, “I’m in the mood for a tasty glass of vinegar.” But it helped me through and I tried all these different ones. And you mentioned Holly Whitaker, Glennon, and also Laura McCowen, people who’ve written really pretty amazing books that have been so illuminating and enlightening to me. And one of the things that honestly, I have to say I’m 54, I didn’t know really about alcohol.
Cheryl Strayed:
Abby, you said that it is a poison. It really is. And that too shifted my thinking when I understood that no amount of alcohol is good for you. Now of course, we all consume other things that aren’t good for us too, but to really think about that and take that fact in, the fact that it took me this long to actually know that, and it’s thanks to those books by those women and others, says something about our culture and the culture of alcohol.
Glennon Doyle:
Cheryl, will you tell us anything else that was in that letter of the list of things that you knew about yourself that you wrote to yourself?
Cheryl Strayed:
It’s interesting, because they were all actually about this kind of thing, which is to in some ways love myself. I think that I am really good at looking outward and seeing what do people need from me? How can I support the people in my life, my kids, my partner, my friends, frankly, even readers and fans? How do I put my energy outward in a way that makes them happy?
Cheryl Strayed:
I know how to do that. I’ve nailed that. What I really struggle with is prioritizing myself. And I think this experience with COVID, what ended up happening is I was alone in an Airbnb for a week in Corfu, where I knew not one person. So I’m just in Greece, sick as hell with COVID, and I emerged from this Airbnb and just sat on the street writing that letter to myself. And it was all about how the primacy of the body and how I need to care for me, me and exercise, diet, drink less. And by diet I don’t mean eat less.
Cheryl Strayed:
I mean be more mindful about nurturing myself, nurturing, consuming things that make me feel good, and then the spirit, making space in my life for the things that bring me joy, making space in my artistic life for the things that I actually am curious about pursuing. Again, I’m 54, all my life I’ve wanted to learn how to… This is going to sound insane, but I’m going to say it.
Abby Wambach:
No, it will not. I know you’re going to say something that I want to know.
Cheryl Strayed:
I know you guys are going to laugh and I know I would look ridiculous doing it, but I’ve always wanted to learn how to tap dance. And my husband every year he’s like, “I’m going to give you tap dance lessons for Christmas.” And I’m like, “Don’t. Don’t. It’ll just be a burden, because I don’t have time to learn how to tap dance.” So maybe I need to learn how to tap dance.
Abby Wambach:
Yes.
Glennon Doyle:
You do, Cheryl Strayed.
Abby Wambach:
We are sending you tap shoes.
Cheryl Strayed:
Doesn’t that sound like fun?
Glennon Doyle:
Yes, it sounds amazing.
Abby Wambach:
Yes.
Amanda Doyle:
It sounds absurd. And that is why it’s necessary, because we don’t have any absurdity. We just have this practical shit all day long.
Cheryl Strayed:
I know. And here’s the thing too, what I know is I would laugh the whole time.
Abby Wambach:
Yes.
Cheryl Strayed:
I would laugh the whole time.
Abby Wambach:
Me too. I’m imagining myself tap dancing. It’s so good.
Cheryl Strayed:
And have you ever had this experience? I’ve had this experience lately, because it has been not the easiest time in my life the last few years, and that I actually, when I laugh with abandon, I actually feel it in my body a good thing. It’s like a wave of something really positive.
Amanda Doyle:
Yes. It’s like an orgasm when you’re really laughing.
Cheryl Strayed:
Yes. My new theory is actually seeking that out. Seeking out laughter is one of the most healing acts of love we can give ourselves.
Abby Wambach:
It’s so good. I’ve been doing that exercise with smiling. It’s so weird. But even if you put a fake smile on, I’ll do it for a few minutes a day and I feel ridiculous doing it.
Glennon Doyle:
It looks ridiculous.
Abby Wambach:
But I actually feel better. There’s something chemically happening. I know it for sure in my bones, so just go out there and laugh. Find laughter and also just smile to yourself.
Glennon Doyle:
Cheryl, we were just talking to Gloria Steinem and she said that one of the many reasons why laughter is so magical, is because it’s proof of freedom. Because people can make us do anything. Like you can be compelled to do anything except you cannot make someone laugh, which is so funny, because that’s the way we use the language. We say, “I made her laugh, I made him laugh.” But it’s the one thing that either has to be faked if you’re going to make somebody laugh, but a true laugh can’t be compelled. It can only be given.
Amanda Doyle:
And it’s one of the only ways you can surprise yourself. In this world where nothing’s a surprise except, oh, we need a new transmission on the vehicle. There’s no fun surprises left in life except when something makes you laugh hard, it’s very often a not expected, you weren’t planning that in your day. And it’s just like we lose the surprise, the unexpected and laughing is like, “Huh, I just surprised myself. What a damn joy.”
Cheryl Strayed:
You just made me laugh, Amanda, because the transmission and oh, the cat vomited again on the floor and the… Do you guys have this life too?
Amanda Doyle:
Yes.
Cheryl Strayed:
My life is all that.
Amanda Doyle:
Yes.
Glennon Doyle:
Yes.
Abby Wambach:
Yes.
Glennon Doyle:
We just had it this morning. Basically all we talk about is when our dog took a shit and when she threw up. That’s what we talk about all day.
Cheryl Strayed:
Well, I have two dogs and three cats, so there’s a lot of that going on.
Abby Wambach:
Yeah, a lot of that for sure.
Glennon Doyle:
Cheryl, I have to tell you a couple things. Abby and I just binge-watched all of Tiny Beautiful Things.
Abby Wambach:
Yes.
Glennon Doyle:
I was scared, because Tiny Beautiful Things is one of the books that I give away the most in the world. I still-
Cheryl Strayed:
Oh, thank you.
Glennon Doyle:
I will always. It’s a magical thing, that book. And I was nervous about them trying to translate it to TV. I felt very protective and oh my God, it’s so beautiful. Are you so happy with it? All the magic of book is in it.
Abby Wambach:
Kathryn Hahn, get out of here with Kathryn Hahn.
Glennon Doyle:
Everybody in the production. How do you feel about it?
Cheryl Strayed:
Oh, well, first of all, I feel so thrilled that you guys loved it. You’re among the very first kind of people outside the project who I’ve talked to about it, so thank you so much. And yes, I am really touched by it and proud of it. I was very involved in the making of it. I was in the writer’s room, which was led by the amazing showrunner and creator, Liz Tigelaar, and a team of just beautiful, amazing writers. And then on the set last summer, watching these spectacular, all the cast and crew bringing their beauty to it and their lives to it, so I’m thrilled. It’s so touching to me to see the ways that that book has traveled and I couldn’t be more excited for everyone to see the show.
Glennon Doyle:
It’s so beautiful. For anyone who doesn’t know, can you talk to our audience about Dear Sugar and how that all started and what it has become to you?
Cheryl Strayed:
Yes. So back in early 2010, I had just finished the first draft of Wild and I sent it to my editor and I got this email in this sort of downtime that I was waiting for my editor to get back to me with Wild Notes from Steve Almond. At the time, he was just an acquaintance and he’s now my friend. And he said, “Cheryl, I have been writing this Dear Sugar Column for the Rumpus. It’s an advice column. I write anonymously. I know you read it, because I’ve only received one fan letter and it was from you.”
Amanda Doyle:
Early adopter, Cheryl Strayed.
Cheryl Strayed:
That’s right. That’s right. And later I was like, “That’s not true.” And he said, “No, literally you’re the only person who ever read it and wrote to me.” And he said, “Listen, when I got your email, I realized you are the real Sugar.” And he had read my essays in my first novel, Torch, at that time, and he said, “I don’t want to do it anymore. It pays nothing. Nobody reads it. Nobody writes to me asking for advice. Would you like to take it over?”
Glennon Doyle:
Sounds like an offer you couldn’t refuse, Cheryl.
Cheryl Strayed:
Really. It’s like no pay and no recognition? Sign me up. And which I know sounds insane, but I did. I said yes. And that did go on to become some of the really core pieces of advice I give to people over and over again, is trust your gut, trust yourself. Maybe that letter I wrote to myself in Corfu, that’s the place from which I was speaking then too, saying, here’s what you know is true, and it’s the stuff that sparks you to life.
Cheryl Strayed:
So I said yes. And the great thing about writing for no pay is you can do whatever the hell you want to do. And I decided that I wasn’t going to write a traditional advice column where I am the person who knows everything and I tell you what to do. I was going to use story to help save others, because stories have saved me.
Cheryl Strayed:
And I really went in there and essentially wrote essays about many aspects of life, telling stories from my own life, telling stories sometimes about my friends’ lives with their permission. And I just really believed that that kind of storytelling would be something that would help illuminate people’s questions rather than just tell them what I think they should do. And it grew a cult following online. And so over the years, couple years later, I revealed my identity as Sugar and then published Tiny Beautiful Things, which is a collection of these columns. And now there’s a new addition of it out, the 10th anniversary edition with some new columns.
Glennon Doyle:
It’s why everyone listens to you, because what you do is again and again in beautiful new ways every time say you already know the answer.
Cheryl Strayed:
That’s right.
Glennon Doyle:
And is that why the things we do to take the edge off are so dangerous? Because I think we do those things so we can stop knowing.
Cheryl Strayed:
Yes.
Glennon Doyle:
Right?
Cheryl Strayed:
That’s right. That’s it. You nailed it, Glennon. You want to take over, it’s your Sugar. But no, and that’s it. Over and over again, you see me in the letter saying, “I have absolute clarity about what you should do. Here it is, and not because I think you should do it, but because you think you should do it and you know what you want and you’re afraid to know it. You’re afraid to know it.” Just like that drink less thing, for me, I was afraid to know it, because guess what happens when you know something, you have to act on it.
Glennon Doyle:
You have to do something. Yes.
Cheryl Strayed:
And that’s no fun sometimes or that’s scary sometimes, or that breaks our heart sometimes, at least in the short run. But I promise you, in the long run, you will be better for it. In the long run, the broken heart you will carry if you don’t act on that knowing, is a mighty burden to bear.
Amanda Doyle:
I will never forget your line from the book. The worst thing for us is believing that a lie will keep us safe, and truth is where the danger lies. We hide from acknowledging what we know is true, because we think if we stay on this side of acknowledging it, we’re going to somehow be safe, but we’re never safe there.
Cheryl Strayed:
Absolutely. I know all of us have lived that, and also lived on the other side to be like, I’m not going to say this thing or do this thing or make this move, because it feels risky. It feels like I’ll be endangering myself. And then the journey we all went on as we learned that that was the lie, that actually when you bring things into the light, when you speak your truth, when you live out what you know is the right way, that puts you in the safer zone, because then you’re aligned. The most painful thing is to be misaligned, to have your life out here, be different from your life in here.
Glennon Doyle:
I’m thinking about what you just said when you said, “Glennon, I know you don’t do phone calls.” And I was thinking about how that has become less true over the last eight, nine months of my life when I started recovery and had to take away the thing I was doing to not know a lot… Anorexia restriction. You have to replace things. And so I started accepting phone calls and actually even calling people every once in a while to say, “Help,” whatever people do when they’re hurting.
Glennon Doyle:
And I think it’s so interesting that we have to reach out to people, so that they can act as mirrors for us. Because strangers are writing to you and you’re seeing in their letter one line or two lines that gives you the clue that they already know exactly what they need to do. And then you’re saying to them, “I see you go forth. You have permission to do the thing that you want to do.” And that’s what all the phone calls are about for me. I call the people that I know are just going to mirror me back to me. It’s just so amazing how we all say you already know what to do, and that is half of it. And then you need someone else to see that about you and say, “You have permission to do what you know to do.”
Cheryl Strayed:
Absolutely. I learned this over and over again, that validating, just validating people’s lives and experiences and perceptions about who they are, we all need that. And it’s such a healing act, and it can also be an incredibly motivating one. If somebody can just say to you, “Glennon, I see that this is your struggle,” and that somehow allows you to keep going, right?
Glennon Doyle:
Yeah. Yes.
Cheryl Strayed:
It’s a powerful thing. That’s what connection is, that we for a moment become one. I hear very deeply what you are saying and you feel heard, and then it goes the other way too. It’s a beautiful thing. And when we don’t call people Glennon, we deny ourselves-
Glennon Doyle:
That’s right.
Cheryl Strayed:
… the ability to get that. And I relate to that. I have found myself, and especially when I am feeling sad or struggling or having a hard time with something, I isolate, even the… I think we all do, because you’re like, oh, I don’t want to drag everyone down, because I don’t have a happy story to tell today. And then if I can push through that and go out meet my friends for a walk or tea or whatever, I always feel better. And it’s because of that thing, that connection that’s so important.
Abby Wambach:
I just texted Glennon this yesterday, because we are having some friends events happening over the coming days and she texted me, “Do you think I’ll be okay? Am I going to get through this?” And I said, “I don’t think you’re equating what it could positively bring to you.” What we’re doing is we’re just like, oh, it’s effort, it’s time. But we’re not also bringing into the equation how a community of people or reaching out to somebody else could actually improve your life or improve your circumstance in some way. They might not have any advice or help, but knowing that somebody is there might actually make you feel better about your circumstance.
Cheryl Strayed:
Yeah, for sure. And it might not even be this deep stuff we’re talking about where they’re like affirming. It might just be that you laugh, that you go tap dancing together.
Abby Wambach:
That’s right.
Cheryl Strayed:
That’s important too. Just the joy that others can bring. I have this theory about travel that when we decide to go on a trip, the thing we imagine about that trip is just all the great stuff that we’re going to do and see and it’s just happy. And then you get there and your luggage didn’t make it with you, and you eat some bad food and you have diarrhea, and then you get COVID.
Amanda Doyle:
You get COVID in Greece.
Cheryl Strayed:
My grease trip was a disaster. I always call this retrospective fun. Then you get home and nobody wants to hear your stories about how beautiful the sunset was over Maui. They want to hear your stories about when you almost crapped yourself to death in Guatemala. That is a better story. That’s a longer lasting story. And this does actually have a point, trust me, I’m going to wind back to Glennon getting together with friends thing.
Cheryl Strayed:
So maybe the opposite happens when we think about connecting with friends, or making that call, or getting together where you think you’re imagining all the negative stuff. I’m going to have to get ready and I’m going to have to go somewhere and I’m going to have to be on for a bit. And then you get there and you have a blast. And you think, why was I having so much anxiety about this? This was wonderful. I feel great. Maybe that there is something to remember about that, that you’re going to feel better after you do it and keep that in your mind.
Glennon Doyle:
I think that’s right. I used to feel that way with family trips so much. I think I still do. When kids are little and you go on a family trip, I used to just be looking at them and I’d be carrying all their shit and they’d be crying and I would look at them and think, “One day I’m going to think this was fun.” Right when I get back, I’m going to somehow look back on the… But I was never actually happy.
Cheryl Strayed:
Retrospective fun.
Glennon Doyle:
Yes.
Cheryl Strayed:
Well, it’s a real thing. It really is. It certainly wasn’t very fun to hike the Pacific Crest Trail. It was a lot of things and it was sometimes fun, but mostly it was toil and hardship and pain. And then of course it was the best thing I ever did.
Abby Wambach:
But isn’t life about building memories and not every memory is going to be joyful? But still the memories of traveling with the kids are the things that you take with you everywhere you go.
Glennon Doyle:
Right.
Cheryl Strayed:
Yeah.
Amanda Doyle:
And I think life is about activating all the parts of you. And if we are only staying in this lane all the time, we are not activating and accessing all of the multitude of what we contain. And so many of us are in this like, well, my to-do list is 1400 things long, and I know I owe the people all of these things. And so I wish I had time to be with friends, but I don’t. And I’m a little bitter that people keep telling me to do it, because they’re lucky enough to have time when I don’t. But it’s the only place where this funny math works where that hour that you invest, it multiplies in your life. I don’t know how it works, but it adds more life and margin to you than you put into it. And so yes, you don’t have time. You don’t have time to do it, but you almost don’t have time not to do it, because you need that multiplier in your life. It’s too much.
Cheryl Strayed:
Absolutely.
Abby Wambach:
I’ve been kind of toying with this idea of what makes me feel most alive. And I have figured out that there’s a, before feeling most alive, the thinking about something, the doing of something, when I feel most alive and after having done something, I feel most alive. All of those alive feelings, the feeling it before the middle and after having done something, they’re all important. They all have the same amount of importance in my life and my wellbeing and my happiness. So I don’t know if this makes any sense.
Glennon Doyle:
I like the framing of aliveness instead of what makes me happy. Because if I say what makes me happy, I’m like, I’ll just still stay on the couch.
Cheryl Strayed:
Because happiness has a kind of, it’s sort of lightweight. Aliveness is it’s all the levels of layers. Abby, so how many things are on your list of what makes you feel alive and how many of them do you do on a daily basis?
Abby Wambach:
I love that you asked this, because I’m a data person, so I’ve actually been trying to toy with creating a list of data points, so that I can actually attribute point value to the things that I do. If I’m feeling down or low-
Cheryl Strayed:
She’s such an athlete.
Abby Wambach:
… that I can-
Cheryl Strayed:
She’s like, I won today.
Abby Wambach:
I can put three things into my day and the value of my aliveness will go up. So in terms of the things that make me feel alive before I do them are when I look forward to trips, I feel excited when I look forward to spending time with my family and my kids, things that make me feel alive when I’m actually doing them, golfing, surfing. Things that make me feel alive after I have done them, working out, going on a walk. I know that there are some people who walking. I like having had walked, because I would prefer running. I would like to get there as quickly as possible. Walking feels like the slowest method.
Cheryl Strayed:
How can you not like walk… Well, wait a minute. How are we going to do the AT together, man-
Abby Wambach:
I know.
Cheryl Strayed:
… if you’re going to try to run it.
Abby Wambach:
I know. It’s going to be hard.
Amanda Doyle:
That would be amazing. The camera shot of Abby so far away running and back to Cheryl. It’s like applaud, applaud, applaud, applaud.
Cheryl Strayed:
What kind of person is this? Is this somebody who doesn’t like puppies? How do you not like walking?
Abby Wambach:
Because it’s boring. Because it’s boring.
Cheryl Strayed:
Okay.
Glennon Doyle:
I love walking.
Abby Wambach:
I know you do.
Cheryl Strayed:
Glennon, and you walk every day like me and twice a day. This though, I have to say is probably why Abby is different from us and she’s a champion world-class athlete.
Abby Wambach:
Yes. But here’s the thing, I still attribute the same amount of value to when I walk to when I’m surfing, and to when I’m thinking about going on a trip. That aliveness is the exact same. It’s like I still feel the energy from having walked, so I know that about myself. I know that I have a predisposition to have a little bit of lazy, I like being a little bit of lazy. And to counteract that, I have to remind myself, oh, I feel really alive when I’m done doing a hard thing that whether it’s working out or lifting weights or going on a run, I think that it’s important for people especially to try to build the habits in life that to make you feel most alive.
Glennon Doyle:
So let’s hear from some of our listeners who were so excited to ask the sugar some questions about their lives. Can we hear from Bethany?
Bethany:
Hi, my name is Bethany and I had a question for Dear Sugar for Cheryl Strayed. My question is probably not a super unique one. I feel like basic mom asking this question, but I am in my mid-forties. My kids are growing up and they don’t need me as much. And even before I had kids, never really felt particularly in love with my career or what I was doing. And now I left that for a little while and I don’t know, I kind of don’t know where to go from here. And maybe that’s midlife crisis, I don’t know. But I’m wondering if Dear Sugar has any advice for those of us moms who are feeling a little bit lost in the middle of things. Thanks.
Cheryl Strayed:
Oh, I love this question. Bethany, congratulations. Welcome to your midlife crisis. That is the good news. I really do. I do believe that. Do you know what I mean, guys?
Glennon Doyle:
Yes. It is the best of times. It is not the the worst of times.
Cheryl Strayed:
And it doesn’t feel like the best of times always when we’re in these transition periods. But I do think that this is this wonderful moment, Bethany, in your life where things are breaking open and you say you feel lost. You say you don’t know where to go from here and what an exciting time that is. Because two things, what I want to say is that when we do feel lost, well, then our main task is to go about the business of finding our way. And what that means is you get to go on a journey. You get to follow your curiosity, you get to follow that voice inside of you that we’ve been talking about so far, that voice of inner truth that says, “Here’s what I know about myself.” And the beautiful thing at middle-age, you know a lot. You know didn’t dig your career so much.
Cheryl Strayed:
You know you love your children beyond words and they are needing you less and less as they grow up, and now you have more freedom. And I think so many of us experience that kind of quarter life crisis in our 20s, where the questions are all about the road ahead and all about who am I and where should I go and what direction should I take? And you took the direction you did Bethany, and here you are now 20 years later in your mid-forties. And now the question you get to answer is not who am I, but who am I really? And who you are really is the woman who’s going to get to live this next chapter of your life. And one that possibly, I think I know, in fact, with great certainty will be more aligned with that person you’d most truly are.
Glennon Doyle:
You know what I think about when I think of the word lost as someone who gets lost a lot, because I’m not great at directions for, truly it’s amazing. You know what, when you’re lost, what you also are is very, very alive. When you are taking a route that you’ve known a million times, sometimes life can be when our kids are in our routine, routine, routine, there’s a sleepiness. You can sleepwalk through it, and then when you would’ve lost and think about when you’re in a new place and you don’t recognize anywhere, you are alive to your cells, you’re so aware.
Glennon Doyle:
And I think that is the magic of this time. And it’s like crisis is one of my favorite words in the whole world actually. Everybody talks about crisis as a problem, but it’s actually the root of it is to sift, sifting like where all the sand falls away like in one of those sifters, and you just have the treasures left over. I think stay alive, stay lost, look for the treasures. It’s exciting time. Women were stepping into a time of life when people aren’t needing us. Holy shit, there’s a lot of freedom in that.
Cheryl Strayed:
And I’d say too, Bethany, to really embrace this, actually go after those things that might help you think about what to do next. Go on an actual trip or a journey if you can. If you can’t do that, try to do something outside your comfort zone right there where you live. Take the tap dancing class, if you always wanted to be a tap dancer. Sign up for something that surprises you and see what happens.
Glennon Doyle:
I love it. I love it. Love it. Okay, I think we have Kate next.
Kate:
Hi, my name is Kate. My question is, when you have the clarity to understand that your relationship is not healthy and you can’t stay in it, but you love the person, how do you walk away with grace and dignity, and let go of the resentment and remorse that may have come from the relationship, and just carry on into the light of yourself?
Cheryl Strayed:
Oh, Kate, this is a question that I would say that it’s really one of the very most common questions I get, because it is hard to tell someone you love, that you no longer want to be with them, that you don’t want to stay, that you want to go and you want to go even though you love the person. And that you don’t want to have that goodbye be one that’s one full of anger and wreckage and animosity.
Cheryl Strayed:
And the advice I give over and over again, it’s such a simple piece of advice and so hard to do. But what I know for sure, Kate, is you can do it, is that you tell the truth and you tell the truth with all of your heart and all of your compassion and all of your intelligence, and all of your courage and all of your strength. And you hold within you that little beautiful glowing gem of clarity that contains two truths that are not opposite each other, that you love this person you’ve been in partnership with, and you want to end the relationship as it exists now.
Cheryl Strayed:
And that you always return to that. You say that you don’t want to hold resentment and remorse and all of those things. And I think that that’s about staying mindful about your intentions. Your intentions are to lovingly end the relationship, and sometimes there’s anger and resentment gets tangled up in that. But I promise you, if you can stay true to that deepest core choice within yourself, those things won’t be what dominate your mind or the tenor of this breakup.
Abby Wambach:
Oh, you’ve just solved so many of the reasons why many of my breakups did not end well,
Glennon Doyle:
Both things at once. It’s so beautiful.
Abby Wambach:
I just wasn’t able to be completely honest, I just wasn’t. And I thought it was kindness, but in fact my lack of ability to be completely truthful was probably in the long run unkindness.
Cheryl Strayed:
It’s so true. And Abby, I think that it goes back to this terrible binary thing. I think a lot of people feel like, well, in order to leave, in order for me to say this isn’t working for me and I want to end this relationship, or at least in the way that it exists right now, romantic, sexual, whatever, I want to transition into a friendship or I want to end it all together, whatever it is, is that we think we have to have a reason that is outside of ourselves. It has to be, you’re a bad person. You don’t meet my needs in this way.
Cheryl Strayed:
You can’t just say like, you are amazing and I love you and I’m so grateful for everything we shared and everything I learned from you. And I will love you always in a different way, but I no longer want to be in this relationship. Just to say with simple clarity that truth, I think so many people feel that and are terrified of saying it. And so what they do is then they make it dirty.
Abby Wambach:
Yes.
Glennon Doyle:
They make it dirty.
Cheryl Strayed:
They lie, they manipulate and gaslight. They create conflict where there really doesn’t need to be any. All of those things then end up… We make a dirty break instead of a clean one.
Glennon Doyle:
We demonize the other person, because we think we have to prove ourself… We have to make a case for leaving, because we don’t think we deserve to just go because we want to.
Cheryl Strayed:
That’s right. That’s right.
Glennon Doyle:
So beautiful. Can we please hear from sweet Erica?
Erica:
Hi, my name is Erica. I would like to get Cheryl or Sugar thoughts on how to best love and exist with someone who is in the depth of addiction and depression. It’s not just anyone. It’s one of my most cherished humans on this planet whom I love deeply. It’s my adult son. I do pretty good, but the ache is always there and the pain is sometimes unbearable. It’s hard for me to even say it out loud. It’s a silent pain I feel like I’m always carrying. I would love to hear your insight on this. Thank you for all you do.
Cheryl Strayed:
Oh, Erica, I think that the experience that you are having with your son is way up there among the most painful experiences any of us can have. I don’t think that there’s anything that I can say that would negate that suffering that you’re experiencing, except to say that I think the way you love your son is, I’m going to guess the way that you have been loving him all along, which is wildly, deeply, unconditionally recognizing always that your son is not his addiction.
Cheryl Strayed:
Those two things are not the same. And I think the most positive way you can love him through this experience is to also remember to love yourself. That sounds really like maybe trite sometimes to go, we can’t forget the self-care routine, because I know that that sounds like absolute bullshit in the face of the monumental suffering that you’re experiencing. And yet what I have found and I want to say Erica, even though I haven’t written about this publicly or talked about this a lot, I have had experiences that are like yours, not with a child, but with other family members.
Cheryl Strayed:
And there is this terrible, terrible powerless one feels when you watch somebody you love so dearly suffering and you don’t know how to help them. And what I’ve figured out this love yourself thing, it actually finds its way back to the question you’re asking me, which is how to love your son. And what I mean by this is I think when we’re in pain, we can get very often caught up in this sense, this kind of powerless cycle of what do I do to change him, what do I do to help him, what do I do to support him? And all of those things are so much outside of our control. But what is inside of our control is to say, “How do I make myself strong and brave and whole, so that I can be that strong, brave, whole person that will be there for this person I love so much?”
Cheryl Strayed:
And what that looks like are the little things, literally like the thing I said earlier about seeking out opportunities to laugh, seeking out opportunities to connect, seeking out opportunities, not just to do the deep work. Obviously with a therapist or somebody who can really help you through the epic psychological tasks that you’ve been given, because you’re in this situation, but the things that actually nurture you and make you stronger, braver, wholer.
Cheryl Strayed:
Those are the things that will allow you to be the amazing mother to your son that you already are, because suffering has a way of depleting us, and you are not going to be able to love your son the way I know you want to love him if you’re depleted. So do that and know that actually what you’re going to figure out I think by doing all that stuff is you can bear it. You can bear this pain. And that is love, the strength that you have when it comes to burying this impossible situation is your love.
Abby Wambach:
Damn. Woo wee. Okay.
Amanda Doyle:
Do you think, Cheryl, when you’re talking about finding ways to laugh, finding ways to be whole, do you get a lot of messages like this, that are the thing that she’s not asking that I’m thinking is that old truism of you’re only as happy as your least happy child? Is there something to it that’s like, because of the way the universe is now where my dearest one is suffering, I can only do my best to suffer, because I don’t have the right to ever even try to be happy, because that would be breaking the rules of the universe.
Cheryl Strayed:
I think that’s real, and I also think… With my own kids. I have two teenagers and I think I’ve mentioned maybe to you guys before, that it’s been a hard couple of years and there are times that I have suffered tremendously, because one of my kids was suffering. And that thing you’re describing, Amanda, where it’s almost like you think the greatest act of love is to actually have their nervous system inside your body and suffer for them, suffer in the ways that they are suffering.
Cheryl Strayed:
And what I’ve learned through this experience that I’ve been through is that actually weakens me and that I can’t actually be the mother, the strong, brave, whole mother that I need to be to help my kid who is struggling. And again, sometimes I think this is why right away when I started writing Dear Sugar, I was like, I’m not a self-help person.
Cheryl Strayed:
I do sometimes think that sometimes these messages we get, like just remember gratitude or all these that can seem really kind of glib and false and not really validate the true suffering involved. And the truth is, Erica, that nobody is going to save you from this. That this is one of the most painful things that a human can ever endure and you have to endure it.
Cheryl Strayed:
So then when you just simply accept that, like no magic bunny is going to come along and hippity hop, and then everything is going to be happy and you’re going to feel good about this, you’re never going to feel good if your son is an addict and struggling with depression, you’re just not. But you can feel better in your suffering if you remember to learn how to be strong and learn how to be brave, and to take care of yourself in those radically deep, simple, complicated daily ways that keep you on your two feet.
Glennon Doyle:
That’s why we listen to Dear Sugar.
Abby Wambach:
My gosh.
Glennon Doyle:
She tells the truth. Can we please hear from Miranda?
Miranda:
Hi, my name is Miranda. I started to think about what in my life is the most stressful and what controls me the most, and it’s money. I know it’s not always the most socially acceptable thing to talk about and it can be kind of taboo, but I don’t even care about the money, the figures. I just want to know how to not let it have so much control over my mood and my mental space. That might be too much to ask. Bye.
Cheryl Strayed:
Oh, money. Miranda, I love this question. And I first want to validate, money is absolutely stressful, especially if you don’t have enough or as much as you think you need. I know this, I grew up poor every year of my childhood. I lived under the poverty line and I got Medicaid and food stamps and free government cheese and powdered milk. And on occasion my family visited boots shelves. I got to go to these places at Christmas and pick out a free Christmas gift. I know what it is to live with that stress of money. And I also witnessed that very much with my mom, who was a single mom of three kids and saw the toll it took on her. And I will say it’s exhausting and it’s all you say, it occupies your mind. But the advice I want to give to you, and I love that your question, Miranda, is not about money itself.
Cheryl Strayed:
It’s not about how to earn more money or how to get out of debt or all of those things. It’s actually about your mindset when it comes to stress. And it happens to be stress connected to money, but it could be stress about something else. But what I wanted to say is something that I really absorbed in addition to absorbing the hardships I just described to you of my youth and into my adult life I should say, is that so much of our ability to handle the stress when it comes to money is to make mindful decisions about money’s meaning in our lives. And the ways that money defines who we are and what we feel. The thing that my mother would always say when I was a kid and complaining about wanting something that we couldn’t have or being without, is she would say, “We aren’t poor, because we’re rich in love.”
Cheryl Strayed:
And what I thought at the time as a kid was that was ridiculous, and I rolled my eyes at my mom. But what I realized later is that she raised me and my siblings with a theory of abundance rather than scarcity. So at every turn when I would say, “I want this,” like my whole life, for example, wanted brand name jeans, I wanted Levi’s and Lee jeans, I’d never got them until I had my own job at 14 and bought them myself.
Cheryl Strayed:
I got jeans from Kmart with that had no brand and she would say, “We aren’t poor because we’re rich in love.” Abundance over scarcity, abundance over scarcity. When I became an adult, I started to really think about what does that mean? And I think that part of what it means, and I think this thing applies to stress in every part of our life, is that we become conscious about those received thoughts we have.
Cheryl Strayed:
It’s like, I need more money and so therefore I feel stressed out and I feel controlled by it. What if you take a breath, Miranda, and say, “I feel acutely right now the things I don’t have because of money. What are the things that I do have?” And here we are again in that kind of, oh, just be grateful for everything and you’re going to feel better, but you know what, you actually will. You actually will. You actually will feel better if you can say, “I am rich in these things.”
Cheryl Strayed:
And I think that that can be such a profound shift about so many aspects of our lives. It can liberate us to make choices that actually lead to our thriving that is beyond money. An example of this, one of my favorite questions I get when people talk to me about Wild. So in Wild I write about hiking on the Pacific Crest Trail and I also write about how I had no money. I very often, was hiking with 35 cents in my pocket.
Cheryl Strayed:
When I finished my hike on the trail, I literally had 20 cents. I didn’t have any credit cards. I had had student loan debt that I paid off on my 44th birthday, only 10 years ago. And I just was walking along for literally 1100 miles for 94 days. I’d have a $20 bill in each Visa play box. And then when I spent it was gone. That’s how much money I had. And people will say to me, “How could you have hiked the Pacific Crest Trail if you didn’t have enough money?” And I always say, “But you see, I did. I did have enough money. I hiked the Pacific Crest Trail. If I didn’t have enough money, I couldn’t have done it.”
Glennon Doyle:
You’d still be there.
Cheryl Strayed:
That’s right. And what this is about is that shifting that thinking, what is enough? Am I going to let money be the thing that stops me from going on an epic journey? Am I going to let fear be the thing that stops me from going on this epic journey? The answer was no and no. And this is about the very thing you’re asking about, Miranda, which isn’t about how much money do I have and how much do I need to be happy?
Cheryl Strayed:
It’s how do I change the way I think of the power it has over me? The way you do it is you take the power back. You say, “I am the captain of this ship and these are the things I’m going to remember and think about and feel and allow to have a place in my mind on this day.” And it doesn’t mean you’ll never feel stressed about money again. Trust me, I have spent most of my life stressed about money, but I can say that to make that mental shift will make all the difference in the world in the way you feel about it.
Glennon Doyle:
Cheryl Strayed, I love that every time we talk, we always end up coming back in the end to something that your mom taught you. Every damn time. Every time.
Cheryl Strayed:
It’s true. It’s true. Isn’t that funny to put yourself in the way of beauty that we aren’t poor because we’re rich in love. I think that that’s really powerful stuff, the mom medicine that I received.
Glennon Doyle:
Yeah, and it’s all over the show.
Cheryl Strayed:
Oh my gosh. The show, it’s all over the show.
Glennon Doyle:
It’s all over the show.
Cheryl Strayed:
Mothers and daughters and love and all of that.
Glennon Doyle:
We love you. Your mom and you and your heart and your work just makes the world feel more connected and braver, so thank you, Cheryl.
Cheryl Strayed:
Thank you. I can’t express my gratitude enough, because I really think that the work that the three of you are doing with this podcast is tremendously healing and powerful. I listen to it. I’m a huge fan as you know. I’m going to make you call me Glennon and start talking to me on the show. But also, I hear from so many people all the time about this podcast, and I just hope you know what important work you’re all doing by having these conversations. And so thank you so much for inviting me onto your show and thank you for watching my show, Tiny Beautiful Things.
Glennon Doyle:
Thanks, Cheryl.
Cheryl Strayed:
I always love talking to you. Hey, and anytime you need Dear Sugar back on the show, I am here for you.
Glennon Doyle:
Yes, yes. Heard it here-
Abby Wambach:
I love these episode so much. I’m sitting here, I’m like taking notes. I’m like, damn, that was really good.
Glennon Doyle:
She’s going to go back to all her exes and re-break up with them and tell them the truth this time.
Cheryl Strayed:
Abby is going to break up the right way this time.
Abby Wambach:
That’s right.
Amanda Doyle.
I think they’ve blocked her number, so probably not.
Glennon Doyle:
Yeah, it’s done.
Cheryl Strayed:
Cuz you did it so badly Abby.
Abby Wambach:
That’s right. Thank you, Cheryl.
Glennon Doyle:
Thanks, Cheryl.
Cheryl Strayed:
All right. Bye. Keep walking or running. Bye.
Glennon Doyle:
Bye Pod Squad.
Abby Wambach:
We’ll see you next time.
Glennon Doyle:
I love when Cheryl Strayed is here. If this podcast means something to you, it would mean so much to us. If you’d be willing to take 30 seconds to do each or all of these three things. First, can you please follow or subscribe to, We Can Do Hard Things. Following the pod helps you, because you’ll never miss an episode and it helps us because you’ll never miss an episode. To do this, just go to the We Can Do Hard Things show page on Apple Podcasts, Spotify, Odyssey, or wherever you listen to podcasts, and then just tap the plus sign in the upper right-hand corner or click on follow.
Glennon Doyle:
This is the most important thing for the pod. While you’re there, if you’d be willing to give us a five star rating and review and share an episode you loved with a friend, we would be so grateful. We appreciate you very much. We Can Do Hard Things is produced in partnership with Cadence13 Studios.