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Dr. Nicole Lapera
Hi, I'm Dr. Nicole Lapera. some point in life, many of us notice that our reactions don't always match who we want to be. We shut down, give too much, or pull away, even when it cost us. These habits don't come from nowhere. They begin early, as your nervous system learned how to keep you safe. And over time, they can leave you feeling unsure of who you are or living a life that doesn't feel fully like yours. In my new book, Reparenting the Inner Child, I share practical tools to help you understand these patterns and give you the roadmap on how to create lasting change. Replacement Reparenting the Inner Child is available wherever you get your books.
Julia Louis-Dreyfus
Hi, it's Julia Louis Dreyfus here, and I can't wait for you to hear our new episode of Wiser Than Me with Cyndi Lauper on Amazon Music. Cindy may be a girl who just wants to have fun, but for 40 years she has brought playfulness and a dash of punk to some serious activism. We talk about her lifelong LGBTQ advocacy, her astonishing music career, and picture up a whole lot of wisdom along the way. Listen now, only on Amazon, music included with Prime.
Reshma Sajani
In midlife, I'm realizing I want to do things that are in alignment with my needs. And that's new for me. No guilt, more fun.
Cheryl Strayed
I need a break and I deserve it.
Reshma Sajani
So there's that.
Cheryl Strayed
I want to stop giving a shit what people think about me. And in midlife, I have finally given myself permission to do that.
Reshma Sajani
Welcome to my so Called Midlife, a podcast where we figure out how to stop just getting through it and start actually living it. I'm Reshma Sajani. The further I get into this series, the more I understand that asking for what you want and putting aside any fears or shame you have about doing that, that that may be the key to a more fulfilled midlife. But doing that is really fucking hard. For years, people have written letters to today's guests asking her how to ask for what they want. And Cheryl strayed. She's the right person to answer them because she had to do a lot of soul searching herself to figure out the same thing. And she did that at 26 years old. You might already know Cheryl's story from her award winning memoir, Wild, or from her ongoing Dear Sugar advice column. Her mom died when she was 22, and in the years following, she experienced what some might call a quarter life crisis. And so she got up one day and she just hiked 1100 miles of the Pacific Crest Trail to find her Way back to herself. I wanted to talk to Cheryl because if she was able to make it through that when she was so young, then I thought her midlife was probably a breeze. But what I learned is that that's not really true. I think one of the biggest lessons I took away from Cheryl is that every era is going to have its peaks and valleys and learning to accept that is really where the work is. We also talked about menopause and people pleasing and why women cheat. And Sheryl had some great insights. I hope you enjoy it as much as I did. Let's get into it.
Cheryl Strayed
Hi.
Reshma Sajani
Hi. How are you?
Cheryl Strayed
Good. How are you?
Reshma Sajani
I'm good.
Cheryl Strayed
I've been listening to the podcast and loving it. And the episode I'm listening to right now is the Emily Oster one. And at the beginning you're like, telling your kids to be quiet, so I feel your pain. My kids are gone now, so, I mean, not gone gone.
Reshma Sajani
I saw they're older, right? Yeah. They're both in college, right?
Cheryl Strayed
Yeah, as of last month, they're both in college.
Reshma Sajani
So I know everyone's like, you'll like. Mine are four and nine. They're like, no, no, no, you'll enjoy it. You know, you'll miss this period. And I was like, okay, if you say so. My little one has literally been pooping in his diaper every night. So it's been like this, like at four in the morning, this, like, panic, you know, of like. Anyway, so. Sorry, tmi, too much information.
Cheryl Strayed
No, it's not. I mean, honestly, the best stories. My theory of, of life is the best stories are always poop stories. I mean, I promise you, at any dinner party, I know this is inappropriate conversation, but at any dinner party, if you are like, okay, we're going to go around the table and everyone's going to tell a story about poop. I, you know, everyone will have a story and you'll all be, you know, you'll. Speaking of poop, you'll be peeing your pants, laughing.
Reshma Sajani
All right, that's my next dinner party. I'm gonna do that. So on this show, we talk a lot about midlife and we talk a lot about the midlife mindset. And it varies for everybody. Some people are like, fuck, yeah, best time of my life. And other people are like, oh, my God, this sucks. So I wanna ask you, Cheryl, where do you land? What's your midlife mindset?
Cheryl Strayed
Well, first of all, what I've one thing that midlife has taught me, or I guess a better way to say it is a wisdom that I've really reached in midlife, is that there is no such thing as the best time in your life. Really, you know that I think when I look back, I. I am 56. And when I think about, you know, a lot of times, people will be like, well, what was your best decade? What was your favorite decade? You know? And, you know, instantly, I think, well, every decade of my life has contained real sorrow, real loss, real trauma and real joy, real profound growth and transformation and satisfaction. And I think that is such a better way to think about life, is it's not best and worst. One thing I always say is, you know, our job here is to evolve, and we can't evolve with only suffering, and we can't evolve with only joy. So in the end, we're grateful to have both in all areas of our lives.
Reshma Sajani
It's so powerful. You say that. I always often say, I'm like, God, don't give me everything right now. I don't want it all right now. Like, I want, like you said, to have this life of longing, of wanting, of celebrating, like, all of it.
Cheryl Strayed
Yeah.
Reshma Sajani
Is there something, though, in your 50s that you've discovered that's been a game changer for you?
Cheryl Strayed
Oh, gosh. I mean, I would say my 50s, so much has changed and transformed. There are two decades in my life that I would say I had to really, really grow in a way that ended up being both incredibly painful and incredibly powerful. My 20s, when my mom died, barely in middle age, at the age of 45, and. And I needed to learn how to live in the world without her, which felt unbearable and felt impossible. And then in my 50s, when I was raising two teenagers during the pandemic, and it was very hard, and I was brought to such depths of sorrow and fear and grief that, you know, are nearly comparable to what I went through in losing my mom. You know, that there were so many difficult times where I had to do that. That deep work of going all the way down to the core of who I am and asking myself those profound questions that you must ask yourself when you're forced to grow and you don't want to have to grow. And so, yeah, I would. You know, where am I at right now? I think that I'm in a decade of great transition, and it. And it has brought that. That stuff that I just mentioned, you know, a lot of joy and a lot of suffering and to be able. I'm in the place of that cycle right now where, honestly, Reshma, I'm seeing it A gift. I'm feeling really content and excited and happy at 56, and I feel kind of risen. I'm a few years past men, you know, into menopause now, I guess. I don't know if it's past. I'm in. I. I'm done. I'm not bleeding anymore. And I am entering a new. You know, I call this my crone age. When. When I was so. In the years of perimenopause, when I. When suddenly my period was becoming erratic and I was like. And you have to kind of be like, okay, well, when. When does, you know, menopause officially starts?
Reshma Sajani
Oh, I'm in the perimenopause. I totally feel you. Right, okay.
Cheryl Strayed
So, you know, it's like you're back to being like a teenager again, where you're. You're like, when's my period gonna come? I don't know. And that's gonna be like, every 12 days or every 49 days, you know, and so. But you're in menopause when you don't have your period for one whole year. And so when I was in this erratic stage of not knowing and not knowing, I. I downloaded this app called Big Day, and it's. You can enter any date. Like, let's say you're gonna go to Greece on July 1st. You can be like, trip to Greece, July 1st. You know, and you enter this date, and it's like, it gives you a countdown, like, how many days until, you know, this big day. And so, you know, when I was in my early 50s, like, 51, 52, I would. I would enter, like, when I got my period, and I would. And this is that I'd change the date to set it out, like, you know, for a year, A year, every year. And the title I gave that was crone age. Okay. So, like, I would enter crone age when it had been one year since I had my period. But then finally there was a day that it was my big day. A year came and went, and I had not had my period in that whole 365 days. And I met that day, and I was officially a crone. So here I am in my cronade, and I. Yeah, I'm. I'm. I don't know. I can't articulate for you yet, like, what that journey is, but I'm on it, and I'm going to take it, and I'm gonna learn something big and new, and it's gonna define me for this next era ahead.
Reshma Sajani
I really love that perspective. You did mention your 20s, though, and I wanna go back to that. Your mom passed in your 20s and you kind of have your own version of a quarter life crisis. Your memoir, Wild From Lost to Found on the Pacific Crest Trail, is about how you picked up and left and hiked 1100 miles to just process all this pain. Can you talk about that time in your life and what brought you there?
Cheryl Strayed
Yeah. So, yeah, it was, as you say, a quarter life crisis. I, I think that's a real thing. I think part of it that, you know, many of us in our 20s, we're asking those questions, who am I? What does my childhood mean? Where do I want to go? How do I want to be? And right. You know, when I was 22 and a senior in college, I lost my mother, who was not only my hero, but really my only parent. I, my, my father, I didn't have, I haven't had a relationship with him since I was 6. He was abusive in the time, you know, the short time he was in my life. My stepfather, who I did love as a father, couldn't continue to be a father to me and my siblings after our mother died. And so I was really genuinely an orphan. And it hurt and it was scary and I didn't know how to live in the world without my mom. And that's really true. And back there in my 20s, I, you know, I had always been an ambitious kid. I was, I grew up poor and working class, but not, you know, I always dreamed big. And after my mom died, I lost my way in my sorrow. I think that I, I thought I could honor my mom by ruining my life. And so I sort of self destructed. I sort of forgot for a bit who I was. And my hike, my decision to go hike 1100 miles on the Pacific Crest Trail was very much essentially, you know, I used that word risen, just recently. It was me rising to myself again and seeing myself quite clearly and knowing that really, you know, the way to honor the people who loved us, the way for me to honor my mom would be for me to become the woman she raised me to be. And to do that, I had to, I had to find my way back to strength and power. I knew I had to do something alone. I knew I had to do something that would test me. And I had grown up in the wilderness of northern Minnesota. I knew the wilderness made me feel whole. And so that's how I came upon this decision to go on this journey.
Reshma Sajani
And what did that teach you? What did having that quarter life crisis, riding wild what are the lessons that you Learned in your 20s that kind of helped you? Now, what you said was when you were essentially in your 50s, you have a similar moment where you feel like you need to rise.
Cheryl Strayed
Yeah. Well, I think that the biggest thing that it taught me, and this doesn't necessarily seem like a word that's connected to rising, because when we think of rising, we think like, o, You're. You're there on the mountaintop. Right. But the word that I would say, the biggest lesson was about acceptance. It was about accepting that we can't live on the mountaintop.
Reshma Sajani
Yeah.
Cheryl Strayed
And also that even if we do get to that mountaintop sometimes in our lives, and we all do, then you keep walking and guess where you have to go. You have to descend. You have to walk through the valley again. You have to toil upward. And that, you know, that is about. That's acceptance. That that part of life is those peaks and valleys. You know, the things that we end up feeling grateful for. Some of them are beautiful, easy, lovely. And some of them are miserable, hard, desperately painful things. And to accept all of that is, to me, I really, you know, the la. The last line of wild. You know, how wild it was to let it be. How wild it was to let it be. And that is, to me, about acceptance. It's saying how wild it is to let all of the things that are true about my life, the pretty things and the ugly things, the hard things and the easy things, how to let them all be true and claim them all as mine.
Reshma Sajani
Yeah. Can I ask you. So. Because you. You brought it up. I'm so. Keep thinking about it. So I have several close friends who have recently lost a parent or are dealing with a parent who has cancer or Alzheimer's. Like, I'm in that age. Right. And it is undoing them or cracking them open. So how do you. What's your advice for women who are going through that grief of losing a parent at this stage of our life? And how do we prepare for the loss that we know is inevitably coming?
Cheryl Strayed
Yeah. I mean, I think there's no real way to prepare because there's nothing like losing a parent. And what you feel is all this stuff, all the many varied feelings, positive, negative, sad, you know, whatever it is, regret, remorse. One of the things that I always return to whenever anyone asks about how to prepare is actually to do the reverse and be here now and think about the ways that you can make whole what doesn't feel whole between you today. You know, don't wait for that Deathbed moment, you might not get it. And you can't control other people, right? You can only control yourself. And if you have something to say, and maybe it's that you need an apology, you can, you know, solicit one. That doesn't mean you're going to get one. But to be brave and vulnerable in ways that may be, you know, ultimately healing for you, even if in the end you don't get what you hope to get.
Reshma Sajani
God, that's so hard.
Cheryl Strayed
I know. It's so hard. You know, and so often too, like those things that we're asking for, you know, even if we ask for something, like, I remember I even wrote about this, you know, when my mom was dying. And yes, I was at a very different time in my life. I was in college, you know, I was a 22 year old. I remember just asking my mom, was I a good daughter? You know, which is sort of a ridiculous question. I knew my mother loved me. I knew she thought I was a good daughter, but was I? I needed her to say that over and over again. And even though she would, then when I asked her, she would say it wasn't, it wasn't really what I wanted. That wasn't really my question. My real question was, can you please stay? And I come up against this a lot in my work as Dear Sugar is that very often people have a question for me and that's not actually their question. The real question sits beneath the question they're brave enough to ask. And, you know, the reason I couldn't ask my mom, can you please stay? Is because I knew that the answer was, no, she couldn't. And that's one of the painful truths when we have to watch somebody die. And so, I mean, I think that in the end, what we all have to do is learn how to fill the holes made by, you know, our fathers and our mothers and anyone else who wounded us. We have to fill them ourselves ultimately.
Reshma Sajani
Yeah.
Cheryl Strayed
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Reshma Sajani
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Julia Louis-Dreyfus
hey there, it's Julia Louis Dreyfus. I'm back with a new season of Wiser Than Me. The show where I sit down with remarkable older women and soak up their stories, their humor and their hard earned wisdom. Every conversation leaves me a little smarter and definitely more inspired. And yes, I'm still calling my 91 year old mom Judy to get her take on it all Wiser Than Me from Lemonade Media is out now, wherever you get your podcasts.
Leah Greenberg
Hey everyone, it's Leah Greenberg and Ezra Levin.
Ezra Levin
You might know us as two of the lead organizers of the no Kings protests. We're also the co founders of Indivisible, the grassroots movement organizing against Trump's regime.
Leah Greenberg
And this is what's the Plan? Your weekly guide to the state of our democracy and how we fight back. This is not canned talking points. It's a real live discussion space for the pro democracy movement. We wrestle with strategy together. We take your top voted questions in real time and we talk about the most impactful actions we can take.
Ezra Levin
Right now, democracy is a participatory sport. The fascists win. When we sit on the sidelines. What's the Plan is about how we get into the game.
Leah Greenberg
What's the plan? Available Friday, January 23rd wherever you get
Ezra Levin
your podcasts, subscribe, recruit, discuss, organize and win. That's the plan.
Reshma Sajani
I want to talk about marriage and infidelity because that's a theme in Dear Sugar. Why do you think people cheat? And is it different for women?
Cheryl Strayed
That's an interesting question. I think people cheat because just like they're human. I mean, I, I think that, and it's unfortunate that we, you know, I feel like we, we'd all be so much better at monogamy if we could just like from the get go be like, okay, listen people, this is actually, it's, it's doable, but it's challenging you know?
Reshma Sajani
Right. Like, I might not be perfect. I might not have, like, a perfect record here, but let's just get that out right in the beginning.
Cheryl Strayed
Right. Well, and. And I mean, even with that, it's like. I mean, even if you do have a perfect record, that it's, you know, the story we've been told from, like, way beginning, like when we're like, the fairy tales and everything. Right. All the. The, you know, Disney movies or whatever, like that. That's like. That's the standard. That's the easy thing. That's what real love is, and that's what couples do. You know, they fall in love, they. And then they live happily ever after. Like that. Like, it literally just begins and ends in the same place. Right. And what we know from actual real relationships is even people who are monogamous. My. My husband and I have been together many years, and we're monogamous. You know, that doesn't mean that there haven't been, like, challenges along the way, you know, that, like, if we could just have a more honest conversation about human sexuality, which. Which isn't inherently, you know, mate for life, that we could then more openly say, like, okay, let's. Let's actually, like, grapple with these things in a more honest way. I think more people would be successful. You know, most people do at some point in their lives, find themselves, you know, when it comes to sex, at odds with their own ethical code and morals. I know I certainly was in my first marriage. As I wrote about in Wild and Tiny Beautiful Things, I wasn't faithful to my. My first husband, and I felt terrible about that. And I thought I was an awful, hideous person. And I learned a lot from that experience, and it honestly made me a much, you know, stronger person in that regard, a better partner. But I think that, you know, part of my agony was just feeling like, what's wrong with me? Like, is something wrong with me? And, you know, I love that, you know, people like Dan Savage, who writes the Savage Love Advice column, you know, just normalizing different kinds of sexuality and normalizing monogamy being a fine thing, but also a challenging thing for many people.
Reshma Sajani
So is that hard for you because you write about how in your second marriage, your current husband, Bryant, he did cheat on you.
Cheryl Strayed
Yeah. Before we were married, when we were first dating. Yeah.
Reshma Sajani
And you talk about how, like, you wrote about the phone call that gave you this, like, gut feeling that something wasn't right.
Cheryl Strayed
Yeah.
Reshma Sajani
How did the both of you work through it?
Cheryl Strayed
Well, and one of the things I write about that is as painful and awful as it was. I'm actually grateful for it now because it did exactly what I was just saying. It opened up a conversation between us that wasn't about the fairy tale, that was actually about human sexuality and, you know, his wounds and my wounds and our hopes and expectations and aspirations as a couple. You know, the question, you know, at that time when, when he, you know, he basically had a one night stand and, you know, it wasn't his problem, wasn't like, well, I'm not sure I'm. If I'm in love with you, Cheryl, I'm not sure if I want to be partners with you. That wasn't his question. His question was really, it frankly had nothing to do with me. It had to do with his own, you know, ability to kind of like say no to himself and manage. Manage certain impulses and desires. And we had to talk in a much more honest way to each other in a way that was sort of painful. And frankly, I think that part of my ability to understand where he was coming from and ultimately forgive him and come back together with him was because I, I related, like, I understood when he was like, yeah, it was just one thing. And then this thing and then this happened. Like, I was like, you know, I get it because I've been in that situation too. Esther Perel also talks beautifully about this. You know, we. We cheat. You know, you asked me, why do people cheat? Well, we cheat for any number of reasons. And many of them have to do really just with our own sense of self worth, feeling desirable again for that novelty and excitement, you know.
Reshma Sajani
Yeah, she certainly says that. She says, you know, because the incidence of women cheating are much higher. And she says it's just oftentimes that women just want something for them.
Cheryl Strayed
Yeah.
Reshma Sajani
So they have this affair, they have this lover, they have this thing that is just for them in a world where they feel like they don't have anything for them. And that's. I found that always very powerful. One of the things that you, you started writing Dear Sugar when you were 41. And you said, when we boil it down, we collectively have five to six problems that most letters fit into. What were those reoccurring problems? What were those five to six problems?
Cheryl Strayed
And, you know, so, yeah, the Dear Circuit column, I started writing it at 41 and then it's gone. It's had different iterations. Right. You know, it was like I wrote it on the rumpus. And then it was a book, Tiny Beautiful things, and then it was a podcast With Steve Almond. And then now I do it as a substack newsletter monthly. I'm on a little hiatus right now, but I've been writing the monthly newsletter for the last month, last maybe four years and. Yeah, and that's still true. Those, those kind of buckets of problems, if you will. And you know, they're like the dysfunctional, painful childhood. Those, those kind of family of origin wounds is one bucket. One is the whole, you know, sex, marriage, love, romance, that kind of thing. One is. I mean, I, I'm forgetting them all now, you know, but, but it's like. Or, you know, the, the career, like, where am I going? What do I, you know, my dreams and my work life and, you know, where should I live? And those kind of life, like lifestyle, adult problems. I, I call jokingly. There's one. One of the five areas is, you know, problems with my vagina. You know, it's like, you know, it's like fertility or should I have a baby or not. And like, you know, vaginal, what the terrible thing they call vaginal atrophy, you know, like all of that, you know, so it really is kind of reassuring, actually. I always find this, this is my. One of my favorite things about being a writer and not just an advice columnist, but frankly, just a writer, is, you know, the struggles that we have are so universal. You know, we almost always feel like we're alone and we basically never are.
Reshma Sajani
Why do you think people don't share that sense of, like, vulnerability or that. Why do we front?
Cheryl Strayed
Well, because of everything we've all been trained to do from day one, which is essentially to be pleasing to others so that they will love us and include us. I mean, there, there's really like a very primal fear, I think, about being cast out and considered bad or wrong or weird or unlike the others or in some way violating those. All of those unspoken codes that, you know, so when we step outside of that, it's incredibly scary because we risk not getting that. That thing we really need at core, which is acceptance and love, you know, so I understand why people are afraid of it. And it's one of those. It's like a trust fall. It's like just do it, you know, speak that sentence out loud that you're afraid to speak. And you know, the other thing, I think too, so many of us, especially as women who are people pleasers, and I am just like, you know, I am like the captain of the squad, of the people pleaser squad, and it's been quite a journey to try to Step back from that. And it is. That really is about, you know, stating what you want and need. You are part of the equation. And I can't tell you how many years it's taken me to learn that lesson.
Reshma Sajani
Yeah, I was just with Gloria Sanom, and she said the biggest advice I can give to women is just. Just say it out loud. Just say it out loud. And you would think about so many things that happen to women, whether it's rape or sexual abuse or, you know, something at work or something, if they just said it right, not only what that could do for changing the condition of women. Well, what they could do for themselves and feeling bravery and empowerment. And I think the remember is like, it doesn't always feel good to be brave.
Cheryl Strayed
Yeah, it doesn't. But. And I think, too, that this is so connected to shame that it's like when we decide not to say something. I mean, this is really. Even comes in with age. All of my life I've heard that thing never. What. What. What's that rule?
Julia Louis-Dreyfus
Right.
Cheryl Strayed
Never ask a woman her age, which just by the way, I rejected that as, you know, since I was a child. You know, the only reason not to ask a woman her age, the only reason that's ever been considered impolite is because, what, are we supposed to be ashamed? We're supposed to be ashamed to be 42 or 36 or 56 or 78. And, you know, so what I say, it's almost my, like, personal, like, tiny little resistance, my little revolution, my revolutionary spirit is saying, you know, say who you are and say it out loud.
Shan (ASEX certified sex educator)
Only 18 states require sex ed to be medically accurate. And relationship classes.
Cheryl Strayed
Let's fix that.
Shan (ASEX certified sex educator)
I'm Shan, an ASEX certified sex educator with a master's in psych. And on my podcast, Lovers by Shan, we make learning about love as mind
Cheryl Strayed
blowing as making it.
Shan (ASEX certified sex educator)
Celebrities and fascinating people share an intimate story. Then we uncover the lesson for all of us. Watch Lovers by Shan from Lemonada Media on YouTube or listen wherever you like. Your podcast.
Reshma Sajani
I Want to Talk About Success. Wild came out when you were 44 to a ton of success. Right? The movie's released two years later. Tiny Beautiful Things, your book of Dear Sugar essays has been adapted into a Hulu series, which is amazing.
Cheryl Strayed
Thank you.
Reshma Sajani
I love it. Everybody watch it because it's so powerful. I laughed, I cried. I felt uncomfortable, like I told you. Cheryl, do you feel like you made it?
Cheryl Strayed
Oh, yeah, yeah, definitely. Definitely. And that feels amazing.
Reshma Sajani
Ah, it feels amazing to hear you say it.
Cheryl Strayed
Oh, I Know, I know we're not supposed to say that, right? No, you are.
Reshma Sajani
We are supposed to say it.
Cheryl Strayed
So thank you for saying, oh, no, but. No but. And, but here's something I want to say. I felt like I made it before that, you know, so, yeah, you're right. Wild came out in 2012. That was the year. So it was 43 when I was published. I turned 44 that year. But several years before that, I had published my first novel, Torch. And honestly, that is. That is when I felt like I had made it. Okay. And I want to explain this a bit, because that had been my dream. To publish a book, to publish a novel had been just really the dream. The dream that I had carried with me, you know, from childhood when I first learned how to read and fell in love with words and then onward. And it was the thing. I was like, okay, this is the thing. I must do this. I am called to do this thing. And that's when I really felt like I made it. And then when Wild came out and became this, like, international bestseller, then it was like, okay, this has gone way beyond. This has gone way beyond. This isn't my dream. My dream was. Was not like international bestseller. My dream was publishing my. Publishing a book. And so what's so cool about that, and I think I'm so grateful that I was, you know, 43 when that book was published and had that kind of fame, is that I just got to experience it. Experience that. Not as self defining, but rather like, well, isn't this fun? Isn't this interesting? Isn't this wild? No pun intended. Isn't this something I just honestly never would have dreamed? And, you know, to sit there, I had so many moments. I remember sitting at the Oscars, you know, just hanging out at the Oscars, and both Laura Dern and Reese Witherspoon were nominated. Reese played me and Laura Dern played my mom. Both of those women are dear friends of mine. Now, I just actually had lunch with Laura yesterday, and it was this moment. They played a clip from the movie when they were announcing Laura's nomination. And in it, there was Laura talking to my daughter Bobby, who played the young me. And she's dressed in clothes that are like exactly like an outfit my mother wore all the time. And she's talking to this young girl who is my daughter, named after my mother, Bobby. And I just remember watching that clip, sitting in the Oscars and just thinking, I never could have imagined this. You know, it was beyond.
Reshma Sajani
Wow.
Cheryl Strayed
And I just. I did that thing that we were just talking about, you know, we remember that we stand on the shoulders of the people who came before us. And I thought so much about my mother. I thought so much about maybe all of my. All of the female ancestors who came before her. I'm standing on their shoulders. And, you know, so, yeah, I made it. Yeah. And I didn't make it just for me. I made it for all of the ways that they sacrificed and suffered and loved and gave and contributed to the betterment of the world. And me.
Reshma Sajani
Yeah. I want to talk about what's next. I read that you said, now here I am in middle age, wondering what's next? What's the next era about? I can feel in my bones that a journey is coming.
Cheryl Strayed
Yeah.
Reshma Sajani
And my kids leave the next. In a couple years they have left. And I'm longing for a journey to help me see the road ahead clearly. Seems like someone's pretty excited about this next act, huh?
Cheryl Strayed
I am. I am. One of the things I learned about my hike on the Pacific Crest Trail when I was riding wild is I could see very clearly that what I had done for myself in my 20s is I gave myself what the culture didn't give me, that. That most cultures throughout time have given young people. And that is a rite of passage. You know, very often in ancient cultures all around the world, it was like, you know, when. When young people are going through that transition of really becoming adults and stepping into their independence and their strength, they are asked, you know, they are. They're supported and asked to go on a journey where they. They're tested against themselves. They get to find out, you know, how brave they are and how strong they are and how resilient they are and how. What capacity they have to continue stepping forward even when it hurts. And I realized that, you know, that we don't just need to do that once in our lives, you know, that we need to really think about the other times that we transition. Anyone who's gotten divorced has to walk through a profound transition, or most people who've divorced have to. Anyone who's recovered from a terrible loss, you know, an illness, or, you know, losing somebody they. Who they love, you know, you have to transition. And that very often is done most powerfully when we can actually take some time and be contemplative and remember again who we are and see for the first time who we're now becoming in this new reality. And I think that that's so much what's happening for me right now.
Reshma Sajani
I can't wait for you to write about it.
Cheryl Strayed
I'm writing about it. I am already.
Reshma Sajani
I can't wait. I can't wait to read it. I can't wait to read it. And I'm sure all of our listeners can't wait to read it too. Cause it's just you are so gifted and so powerful and so, so spot on with how you describe. And I think this moment of midlife is like there aren't all the words yet because we haven't focused enough attention on it. We haven't given it enough attention.
Cheryl Strayed
We haven't. I mean, you know, you hear this over and over again. I. And you know, I think that I love middle age. I mean, I think it's a really interesting, incredibly powerful and fruitful time. And I think too that I've always just had a very positive feeling about this, about this time in my life. And part of it is honestly that when you lose your mom at 45, you understand what a privilege it is to get to live into middle age and to get to be old. I hope I get that.
Reshma Sajani
Well, thank you so much for this powerful conversation and I just, I can't wait to hopefully be a part of what you're doing next. So thank you.
Cheryl Strayed
Such a pleasure to talk to you.
Reshma Sajani
Cheryl Strayed is an author and advice columnist. Make sure you check out her Dear Sugar on Substack. She's on a hiatus right now, but you know, she's gonna come back with more wisdom, more candor, and just more words that are gonna knock your socks off. And in the meantime, I'm gonna be taking her advice to live for right now, to be present. I'm not gonna wait for a deathbed moment. What about you? What's your takeaway from this episode? If you ever have a thought or a question about something we talk about on this podcast, I want to hear from you. You can leave us a voicemail at the link in show notes. That's it for now. See you next week for our menopause episode. It's going to be a wild ride just like Midlife. Bye.
Cheryl Strayed
Bye.
Reshma Sajani
There's more of my so called midlife with Lemonada. Premium subscribers get exclusive access to bonus content like Midlife advice that didn't make it into the show. Subscribe now. In Apple Podcasts, I'm your host Rashmi Sajani. Our producer is Claire Jones. This series is sound designed by Ivan Koraev. Our theme was composed by Ivan Korayev and performed by Ryan Jewellery, Ivan Kuraev and Karen Waltok. Our senior supervising producer is Kristen Lepore. Our VP of New Content is Rachel Neal. Executive producers include me, Reshma Sajani, Stephanie Whittles Wax, and Jessica Cordova Kramer. Series consulting and production support from Katie Cordova. Help others find our show by leaving us a rating and writing a review. And let us know how you're doing in Midlife. You can submit your story to be included in this show@speakpipe.com midlife follow myso called Midlife wherever you get your podcast or listen. Ad free on Amazon Music with your prime membership. Thanks for listening. See you next week. Bye.
Cheryl Strayed
Foreign.
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Podcast Summary
My So-Called Midlife with Reshma Saujani
Episode: Revisit: Embracing Your Crone Age with Cheryl Strayed
Date: April 1, 2026
In this engaging episode, host Reshma Saujani sits down with bestselling author and advice columnist Cheryl Strayed to discuss the realities of midlife—what it means to truly embrace this transitional era, the lessons learned, and the work of letting go, accepting, and finally, living fully. Touching on deep personal stories and hard-earned wisdom, the conversation ranges from grief and transformation to menopause, marriage, infidelity, and the importance of speaking our truths.
The episode is candid, irreverent, and compassionate, weaving humor and vulnerability. Cheryl’s wisdom is hard-won and unpretentious; Reshma brings authentic curiosity and reflection, creating a relatable space for listeners navigating their own midlife transitions.
If you are seeking permission to embrace your own evolution, question the “best years,” or acknowledge all your mess and your triumphs with radical acceptance, this episode is for you.
Reshma’s take-home message: “Live for right now, be present, don’t wait for a deathbed moment.”
Cheryl’s personal goal: To learn and define her “crone age,” embracing the next era with courage, self-acceptance, and curiosity.
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