What do you do when life doesn't go according to plan that moment you lose a job, or a loved one, or even a piece of yourself. I'm Brookshields and this is now What, a podcast about pivotal moments as told by people who lived them. Each week, I sit down with a guest to talk about the times they were knocked off course and what they did to move forward.
Some stories are funny, others are gut wrenching, but all are unapologetically human and remind us that every success and every setback is accompanied by a choice, and that choice answers one question, Now, what have your children ever if they read everything that you've written? Do they what do they feel about it?
They've read little bits of my work, and they've sometimes been in the room when I've read work or talked about it. But neither of them have yet like sat down and read my books, which is kind of interesting.
It doesn't surprise me.
I think I always have had this idea that, like, when they're about thirty, they'll be able to do that, because you know, my work is so personal, there is so much about my interior life. The other interesting thing is, you know, I'm not sure if you know this book. But my daughter Bobby, who's named after my mother, Bobby, actually was.
In Wild, the movie. She played the young me.
So when Reese Witherspoone remembers her childhood, they're these flashbacks and you see this blonde girl. Well, that's my daughter Bobby, and she had just turned eight and she was.
In the movie.
And even though she was in the movie, they've neither of my kids have ever watched the film. They just think it's too much and it's so funny because their friends have all watched the movie, their friends have read the books, some of their friends have been assigned to read the book in high school and college. And my own kids hapened. But I think that it's also like, really naturally.
My guest today has a way with words. Cheryl Strad is a renowned author, public speaker, advice columnist, and podcast host. Her books, including the New York Times bestseller Wild, have sold millions of copies worldwide and have been adapted to both big and small screen. I loved Hulu's version of her book, Tiny Beautiful Things, and I marveled at both the resilience of her spirit and the quality of her advice.
Cheryl's a celebrated essayist, a wife, a mom to two teenagers, and I just think a genuinely kind person, a conversation with a gift, and I'm grateful to her for allowing me to share it with you all. So, without further ado, here is Cheryl Strade. I'm so happy to talk to you. Nice to meet you, Cheryl.
I'm so excited to meet you.
I was telling my daughter, who just turned eighteen on Sunday, Oh boy, I was telling her this morning, I was going to talk to you, And I was like, if you had gone back in time and told my sixteen year old self that I would ever get to talk to Brookshields, I would never have believed you.
So I was telling her how much I've loved you for so long.
Oh well, thank you. And if you had told me at sixteen that I would be talking to such an accomplished writer person human, I probably would have said, uh, I don't think so like. I'm just like, I'm just like a model and a you know, kind of actress.
Oh well, thank you.
So you've got two kids though, right, I.
Had two kids? Yeah, I have.
My son is a freshman at college. He just started at university of Oregon last month, and my daughter is a senior in high school.
Wow, I've got one who's will be going into her junior year in college. She's a sophomore. And I've got a senior in high school. So okay, I'm sure if I were to ask you advice, you would give me very healthy advice. But people know you from your books predominantly they tell us a lot about you, which I believe, but they don't tell you everything about you. And I
always am interested in how people describe themselves. So if you were to have to describe yourself in your day to day life right now, what would you say?
Oh, gosh, I think that I really am like many parents, It's like they realize, Okay, I'm all these things in my work life, but my main job is mommy.
I'm a mom.
And I really had this idea when my kids were younger that when they got to be teenagers, that would be a time that I could like kind of step back and you know, you don't have to follow them around at the playground anymore, but you have to do other things that are really, I think equally demanding, and especially these last few years brook where it's been what I think of as like very high impact parents through a pandemic and all of the changes that COVID brought
on in terms of like my kids were not in school for a long time, they were navigating adolescents, which is this time when, of course, all they wanted to do was be with their friends. So it's been really a very consuming part of my life. So I'm a mom. I'm a partner to my wonderful husband who I've been with since really I met him nine days after I finished my hike on the Pacific Crest Trail, which I
wrote about in Wild, my husband, Brian Linstrom. And of course I'm a writer, and as a writer, I wear many hats. When I first started writing, I always thought that I would be somebody who just wrote books. And what's been really cool and fun about my career, and I think so many of our careers what ends up happening is is as you walk down the path, all
of these other paths open up. My writing led me, for example, to write this Dear Sugar advice column, which I never in my wildest amount and thought, you know, I'm going to write an advice column someday, And to be a really central part of my work, well, I do that or I've also branched out into I write screenplays and I've been involved in television writing as well, and that's sort of a surprise. And then I also
have an accidental career, as you know. I had a couple of podcasts, I do a lot of public speaking. Those are things that were great surprises. So I'm a bunch of different things. And I also am a cat mom and a dog mom too.
We can't forget that.
Okay, Well, I'm interested in, first of all, how you're because you were You were brought up very Let's talk a little bit about your upbringing. And you lived in a very rural community with your mom. Yeah, and that meant what without.
Or a toilet?
I mean, yeah, I had a really well first of all, I was born in western Pennsylvania in Appalasia, my where my father in this tiny town where my father had grown up and his whole family, his father and grandfather, were coal miners, and so I grew up, you know, came from very humble beginnings. My parents had married in the sixties because my mom, when they were dating, my mom got pregnant and it was a very difficult marriage.
They had three kids together. I'm their middle.
Child, and by the time I was six, my parents were divorced and I was living in a little town outside of Minneapolis, about an hour outside of Minneapolis, where my mom was a waitress and worked in a factory, and we were you know, we received welfare, we were poor. We were basically living hand to mouth, and by the time I was a teenager, we had moved to northern Minnesota,
where we essentially were homesteaders. You know, we lived in the woods, we built our own house with my by then my stepfather, who was a carpenter, and we you know, my mom and stepfather were in some ways kind of back to the landers.
You know.
My mom certainly had a lot of values that were out providing for yourself and growing your.
Own food and making things. But also we were broke.
You know, we didn't have an indoor toilet, not because of any sort of political ideology. It was because we couldn't afford to have one installed until I was actually away at college. And so I grew up in a really rustic way. I grew up with a lot of financial struggle and strife, but I also grew up in a really happy you know that was in so many ways very much nurtured me and made me who I am today.
How So, because I you know, you hear that story more often than you hear you know, those born to privilege, you know, don't have the understanding of have not or or whatever. But how do you think that that that experience and the memory of that experience from such a young age, for as many years as you experienced it, how do you think that that differentiated you or shaped you differently and different from your peers.
Well, it's such a big question. I mean, we could talk this whole hour about that, because I really do think that, you know, when we use that word privilege, we think of just a very specific things. And of course, you know, people who have in this case, like economic advantages that I didn't have have more. I also just want to share with you, Brooke, there was something that my mom would always say to me, we aren't poor
because we're rich in love. And so there's a way in which I was poor and unprivileged, and there was a way in which I was rich and extremely privileged. I have so many dear, dear friends who grew up with great economic privilege and were poor in every other way, and so I think it's really important to remember that because love is the essential nutrient. I wrote that as sugar, and I do believe it. And so an answer to your question is I got plenty of that.
I had very.
Difficult experiences and trauma with my father, witnessing him physically abuse my mother. I have also myself been a victim of sexual abuse as a child. But and that's a big but I had to heal those wounds. This isn't to diminish that, but I did have a mother who really loved me and my siblings, and she always made us feel safe and secure, even when we were, you know, really financially precarious and insecure.
And this was with your real biology, my biological father.
So he was violent and abusive and menacing, and that those were really painful things. But my mother, you know, eventually steered us out of there, and you know, we I do think that that so many of the things that made me are those difficult things, but also my mother, who modeled resilience, who modeled the ability to walk in the direction of the better thing.
You know.
I think think it's funny that, like I'm sort of famous for walking, and I think like I can trace that back to witnessing my mother walk walk out of a marriage, walk away from something that was harmful, even though that was, you know, all these other ways difficult to do, and she was a very really self sufficient person.
You know.
I can describe my childhood in a lot of ways where I say, well, we didn't have an indoor toilet, or we didn't have this, or we didn't have that, But I could also tell you so many things we had what.
Has mostly helped you? How do you heal from that pain?
Yeah?
How did you know to do that? Because it's got to be practiced over the years.
It does. That's it.
I mean, you put your finger on it. It is, you know that we find healing through learning how to tell our stories and also to revise our stories to be able to have some perspective. I have always said, I really do believe in the power of art because it is essentially telling us the story back to us of what we already know. What it means to be human, what it means to love, to lose, to heal, to triumph over over the things that have traumatized us, you know, and so so much of I think the way we
think about the world is dichotomy. Right, You're either a victim or you're not, or you're weak, or you're strong, or you're this, or you're that, you're damaged, or your whole you know, you're broken, or your whole. And I have always been such a believer that we're all of those things at once that I can say to you, yeah, those I had some horrible traumas as a child, and those things don't just go away because I snap my fingers.
They are always with me. But over time, what I did is I learned how to allow myself the pain of those experiences. I allowed myself the understanding of those experiences, and I allowed myself to tell i'll revise story about those experiences.
Now.
Of course, it took something from me to be sexually abused by my grandfather, for example, it also eventually gave me something back in my ability to understand how it is sometimes those who are suffering make other people suffer, how it is sometimes we have to walk through and learn how to carry those ugly things we wish we didn't have to carry, and how we can let those negative experiences make us actually not only stronger, but able to help others by telling the story of that experience.
I'm so deeply moved by your insight, you know, in your compassion. You Now if you've done a lot of therapy.
Too, you know I haven't.
That is Oh, I hate you. I've been in therapy forever and it's the only reason why I feel sort of, you know, grounded. I know, yes, is you naturally this?
I mean I think that this is my interviews.
I've never been through therapy, you know, really, so, I mean I've done I've done therapy like with my kids and stuff like that, but I, like myself, have never fully gone through therapy. But let me tell you. My theory of that book is that because at first it
was really just a socioeconomic thing. Like I didn't grow up in a culture or community where people went to therapy, you know, Like I have friends who grew up in New York City in LA and they're like they were in therapy like age eight and a half, you know what I mean.
It's just like how it is.
And like I grew up in northern Minnesota, and also I'm fifty five, so generationally, like it wasn't just it.
Hadn't really seeped into the culture in the way it has now.
Back when I was younger, so I couldn't and then and then in my young adult years, I couldn't afford it, you know, I didn't have holll insurance. And then now that I'm old enough, it was like, Okay, what I realized is has been such a therapeutic act for me. Accidentally, I was doing what we do in therapy, like when you write about your life, you have to deeply, deeply, you know, interrogate your assumptions. You have to think about other perspectives, like when you wrote about your mom and
I've written about my mom. You know, there is if you're going to actually write something that's worth reading and we're sharing with other people, you have to really struggle to get to the truth.
And the truth isn't just your truth.
And that is one thing that what I've really found from Deer Sugar, which was a popular advice column that you just contributed to right and then it became a podcast, is that.
No I wrote the column.
So I first wrote the column for The Rumpust and I still write it. It's a monthly column. I have a subtech newsletter, but I took so I wrote. I wrote it for The Rumpus for a couple of years. It became my collection Tiny Beautiful Things. Then I stopped writing it for a little while, and I did a podcast for The New York Times in w R called
Dear Sugars with my co host Steve Allman. Then we stopped doing that, and then I picked up writing it again monthly for my Substeck newsletter and recently well to sort of at the same time that the TV adaptation came out. Earlier this year, Hulu released Tiny Beautiful Things, the TV show Starry Katherine Hans Katherine Han, Who's amazing, And at that time we reissued Tiny Beautiful Things the tenth anniversary with some new columns. So it's really like
this whole deer sugar giving advice thing, Brooke. That's such a prime example of when I said, all these paths presented themselves, Dear Sugar has taken me on a journey.
It makes me think that you were, in some way always a listener, a watcher, an advice giver. Do you think that's just in your DNA.
Like I do. I do you know?
And I think it's connected to.
Me being a writer and not just being a writer, but really essentially being feeling called to be a writer. I have always been somebody who felt like the way I could contribute to the world, you know, the thing I had to give was to tell stories, to write stories,
to make people feel less alone through words. And when I think about the things that have helped me in my life over time, it's almost always a book or a poem or you know, an essay that made me feel seen and recognized and validated and inspired or consoled and so in the form of their Sugar, when I had the opportunity to write this column, I first wrote
it anonymously and then revealed my identity as Sugar. I thought, okay, this is interesting because I can use this in a really practical way, like writing can actually be directly helpful to people. And I didn't know, you know, I was like, listen, I've never been through therapy, I've never taken.
A psychology class. But what I did know was the human condition.
I mean, as a writer, that's which when you apprentice yourself to the craft of writing, it's not just forming sentences in metaphors and so forth. It's actually understanding how you know what motivates or animates this person, what scares this person, this character? Right, And so I applied that
kind of thinking to these letters. And as for the empathy piece, you know, yeah, I've always tended to be somebody who suffered at the idea of others suffering, and Brooke one of the things I learned right away is that the only way I could possibly give people advice as sugar was.
I couldn't judge them.
Whatever you say to me about what you did or you regret or your fear or you're you know, messing up, I'm going to say, I'm going to validate you, and I'm going to hold you with with loving kind and I'm going to write to you from that position, even if I ultimately say things that maybe, like, you know, challenge you. For example, you could say, like, you know, we could put out like if we could put a poll out right now and go, Okay, my husband cheated on me, Should I divorce him?
Yes or no?
Like, and then people would like they would vote yes or no based on like whatever actually they bring to it, like their ideas, their assumptions, their history. But the truth is we don't know the answer to that question because actually It depends. It depends on that story, on that relationship, on that situation. And that's what I listened to really closely, that these that this you know, this qualified advice isn't
about just some dispensing what should be. It's listening carefully to what the person who's seeking advice wants and needs and knows and fears.
It can be dangerous, though, can it be dangerous?
Like do you mean dangerous that? Like it's dangerous to say I think you should do this?
I mean delicate or maybe dangerous isn't the proper word. I shouldn't applay it. There's a delicacy with which you know, these are basic strangers. Yeah, okay, so now you're trying to get into their psyche, not just by using your own experience, because maybe you did or didn't have a husband who cheated on you. Right, But like if someone said that, I would say, I can't answer that for you. I can't. I can't say you should divorce this guy
you shouldn't. But I could say, well, tell me a little bit more what led up to this?
Yeah?
And is what's happening in your heart when you realize that?
But here's what I do.
I whether it be even on the podcast. So whether it's on the podcast or in the column, people have written me a letter and they do say more than that. You know, I wouldn't answer a letter that just said my husband, she's obviously I break up with them. They say all the things, and very often what I do in my advice because I agree with you, you're right, it's delicate, and I am so not like signing up for telling people what to do and then be like, whoops,
that was a mistake. Yeah, I say to them, here's what I hear you saying, you know, I hear you saying you don't, you know, believe you'll ever feel safe again in this relationship, So maybe you should trust that. Or I hear you saying you understand that people make mistakes, and your partner is telling you he regrets this, and you feel like that there's a way that you could work this out, So maybe trust that.
Like I very often say back to people, I.
Mean, I'm just using this infidelity as one example, but very often they kind of tell me in their letter what they know they want to do, what their gut is, and what I say is I affirm that and I show it to them. Very often people are afraid to know what they know. They're afraid to know they what they most want because once they know it, they have to act on it. So if somebody is writing to me and saying, I'm an attorney, but I've always dreamed
of being a writer, should I quit my job? You know, and they tell the whole story about how their heart sings when they're writing, an aches when they're writing. I say, like, listen, you know what you want to do. You just need me to say it's okay that you do what you want to do, even if you end up failing, you know, And I think that that's a glorious that to me. You know, it's if the qualification to be what I
am an advice colmnist is to listen deeply. The best advice I can ever give is not listen to me, trust me, I know the path. It's listen to yourself. Trust yourself. You know the path, and you have the power, the courage and the strength to walk in.
I named this podcast now What because it is about those rather pivotal but good or bad moments in our lives. You know, the times that we have to really look at our current reality and ask ourselves, now, what the hell do I do in this scenario? And I'd be really interested to know what and now what moment for you has been or is that? I'm sure we all have many yes, but does one stick out to you?
Well? Absolutely? You know, when I came to the end of my hike on the Pacific Crest Trail.
I had long did it take you again? Remind me?
Because I was out there for ninety four days, and you know, I had really gone on that hike. I was twenty six when I took the hike. I finished it two days before my twenty seventh birthday. And I had gone on the hike really to heal myself. My mother had died very suddenly of cancer at the age of forty five a few years before. And there's no other way to put it. My life had gone off the rails, you know, and I thought I had a kind of awakening moment where I thought, where who am
I anymore? You know, in my grief, I have given up this sort of ambition of being a writer. I had just gotten involved with drugs and just led myself down a self destructive path. And so hiking the PCT was away for me, not so much to change myself, but to find myself again, to come to bring myself back to my strength.
And when I.
Finished my hike, I really had this glorious feeling of what next. And what was cool about being able to ask that question at the end of that big journey is that I felt okay. I felt that I had through taking that journey, grounded myself in a way that even though I didn't know the answer, I didn't know where I was going to live, I didn't know what I was going to do to earn money. I didn't know when I was going to finally see through that
dream of writing my first book. But what I knew is at core I could do all of those things that.
I would be okay.
And if I can also add I'm kind of in that moment right now. I'm fifty five, my son's it's freshmen in college, my daughter's a senior in high school. My children are growing up and moving on, and I
who am I? And I've been really asking myself And it's interesting that I began my answer to you with this journey, this big journey that shook me up and allowed me to see myself more clearly and I have to say, Brook, I think that what's next for me in this next big transition is I need to go on a journey again.
Because I don't know the answer.
To that question.
I know that there's a big life shift on the Herriz very close, and I feel like I need to retreat and do something hard like I did on the PCT in order to see what's next.
It's not a natural journey to success, but I'm curious about the journey to commercial success.
Yeah.
It's a lot to navigate and it's a lot to grapple with, and I'm curious as to how it affected you and if fame in the in and of itself, whatever that word means, has that changed your relationship with other writers? Could you talk to me just a little bit about your journey to success and how it has changed, Yeah, fundamental parts of your life and people.
Yeah, and you're I mean, the first thing I want to say is So Wild was published when I was forty three, and I'm so, so so grateful that I was a real grown up before I became famous and before I had that kind of success for a couple of reasons. One the one is, first of all, it allowed me to write my own definition of success.
Wild is not my first book.
My first book is a novel called Torch, and I before that had published several essays, a couple of which were in Best American Essays. I was a successful writer before Wild was published. Now I was, and by a successful writer, I mean I was successful in the way that most writers are successful, which is to say, known to a fairly small orbit of people who are tuned
into literary America. And I really realized in that, you know, in those younger years, in my twenties and thirties, when I was writing my first novel and writing those essays and stories that were being published, I realized, okay, you know, success for writers or most artists. In fact, I'd say all artists isn't money and fame. What they're doing is they're out there creating and making art and they're barely
piecing together a living. But really the way they measure success is by doing the work, By doing the work and giving it they're all and connecting with an audience, even if it's a small audience. Right. So I really attached myself to that idea of success. That's what success looked like to me. And I was My dreams came true before Wild was published. Then Wild came along, Bam, my life absolutely exploded, bloated. It was an international bestseller.
It was an Opra pick withtherspoons start, you know, all all that stuff. And I felt like I was on a rocket ride, you know. I was like all the all the metaphors. There was a volcano, there was a rocket, there was a tornado. There was everything right, and I was at the center of it. And what was really cool to me is that I because I was a grown up in my forties by then, I was really grounded in this feeling of like, wow, okay, this is this other kind of a success, this very external success.
You know.
It didn't change my life inside myself. I had already felt like I'm a writer and I'm successful, and then this other thing happened. And the biggest change was, for the first time in my life, I could afford to pay my bills without struggling strife. But it didn't shift who I was in the world. Now other people would project that onto me. The other people would be like, oh, you know, now you must be moving to la I live in Portland, Oregon. I'd be like why am I moving?
Why I don't even understand now you must be sending your kids to a fancy school.
No, my kids are still at public school. Like you know. They would project a narrative onto me, and it was uncomfortable.
That happens with people though that's their name. I think people and their nature like wanna because because then then they can criticize it.
Right.
Then they turn around and like, oh, so you're fancy.
Now, well right, and they would say, now people met me think you're just so like down to earth and earth.
Why wouldn't I be like what like what?
I don't understand why I wouldn't be And so yeah, and so that's that whole experience did did change my life, and I will say I'm so grateful for it because of course, what a thing to be able to connect with such a big audience.
But I also think that, like you know, people have said, what does success mean to you? To me and to me, it's the ability to keep working, you know. To me, that's like longevity. If I had to pick one word, it would be longevity. The work is appealing, the registering with other people, making someone laugh, you know, and this is what you're saying you're you're saying that that that ability to do what you're put on this earth for which or you believe you are, that to move people,
to put them in a place where they can experience. Period. You mentioned needing another type of wild type of journey. Do you think there's any ideas of what you might want to do?
I need a mild, A mild journey, A mild.
Instead of wild, Okay, just a little more maybe self loving and less painful.
Yeah, exactly.
Maybe maybe a bed like you know, instead of sleeping on the in the dirt, you know, in the tent.
Yeah, I shoes that fit.
I don't know exactly. I mean, I'm a real and I want to say too, I do think the journey. Obviously, travel is a wonderful way to journey, and it might be the way I choose to journey in this next era to but I think a journey can also be an experience or an era of your life in which
you delve into something deeply. So again, you know, and I use this phrase earlier so that you can more clearly see yourself in your situation or this time of your life, and to answer that big question of what next it's a sort of stepping out of the usual. And you can do that right at home. I mean, it takes some real intention, but you can do that. And I haven't yet figured out what it's going to
be for me. I just know that when something is big as this era of my life, of you know, bringing these two children to adulthood, raising them to adulthood, giving them everything I could give them, when that comes to an end, and of course, and I'm using that very softly because you know, our kids still need us very much.
It's even worse.
Yeah, but you know, a certain time of our of a certain era has come to it is coming to an end very soon, and I need to shake up my life to see what it is next.
And I don't know what it will be.
That was Cheryl Strade. If you want to hear more from her, check out the TV adaptation of her best selling collection of Deer Sugar Collar, Tiny Beautiful Things, streaming now on Hulu. That's it for us today, Talk to you next week now. What with Burke Shields is a production of iHeartRadio. Our lead producer and wonderful showrunner is Julia Weaver. Additional research and editing by Darby Masters and Abu zafar Our. Executive producer is Christina Everett. The show is mixed by Bahed Fraser.