“Most of us are broken”: Author Cheryl Strayed embraces the imperfection of “Tiny Beautiful Things”

The Hulu show “Tiny Beautiful Things,” based on Cheryl Strayed’s book and starring Kathryn Hahn, is a tearjerker. “I love to make people cry,” Strayed said on “Salon Talks.” “It’s really one of my favorite things.”

Strayed is an executive producer of the series in which Hahn plays 40-something Clare, a version of Strayed who has a similar past but never hiked the Pacific Coast Trail, aka the version of Strayed we got to know from her bestselling memoir “Wild” and the film starring Reese Witherspoon. Clare’s life is messy and difficult. She hasn’t written the great American novel like she’d hoped, her marriage is in trouble, her teenage daughter hates her, and no matter how long ago it happened, her mother is dead. Clare, like Strayed, is tapped to anonymously write the “Dear Sugar” advice column – which Strayed took over 11 years ago.

Strayed says you don’t need to be an expert to give advice. “If you speak from your truest voice, by which I mean the deepest one, the most vulnerable one, the one that’s willing to risk vulnerability . . . almost always, it’s going to ring a bell in the hearts of other people.”

At this point in Strayed’s career, where she’s podcasting, producing and has two on-screen adaptations of her work, Strayed says her definition of success as a writer remains unchanged. It’s about making people feel less alone and fostering connection through vulnerability.

Watch the “Salon Talks” episode with Strayed here, or read a Q&A of our conversation below to hear about the process of adapting her column for TV, why she loved creating a show with a female lead in her 40s and how writing as Sugar has made her a better person. 

The following conversation has been lightly edited for clarity and length.

You’ve been the voice behind the “Dear Sugar” advice column for over 10 years now. In 2012, you released a collection of some of your best nuggets of wisdom, the most beautiful letters, and your best pieces of advice in a collection called “Tiny Beautiful Things.” How did you turn these separate entries into a narrative story for the show?

Well, that was an undertaking, let me tell you, because of course, in one way I was sure that this book could be adapted for TV because it is so full of stories. Not only do I tell stories about my own life in the course of giving advice to people, but really every letter that’s written to me is a story. 

People present their struggles and their secrets and their sorrows and their conundrums and all of that stuff in the book, so innately I knew anything rich with story is great fodder for television. And yet when it came to figuring out how to make it into television, it took some doing. Really, Liz Tigelaar, the creator and showrunner, she’s just such a wonderful human and also a really smart and amazing writer. She and I began having conversations and really landed on this idea of the story being very much about this woman at the center of the column, Sugar herself.

I think Liz was really sparked by this notion that I tell stories from my own life by way of giving advice, which what I always hope conveys is this truth that like, “OK, listen, I’m not the one who knows. I’m not like the guru who’s going to tell you all the wise things and tell you how to live and give you instructions.” What I’m going to do is say, “I am right down in there with you. I’m also grappling, I’m also struggling. I also don’t always know.” I always think of myself as almost trying to expand the questions that were asked of me, trying to help through sentences and stories to illuminate the situation in a way that allows the letter writer and everyone reading it to see the situation differently. 

We began from that premise: what if we have a woman who isn’t a guru? Who’s just like an ordinary woman who in some ways has a messed-up life and has made some mistakes and in other ways, has wisdom and experience to share, and who is a writer, whose calling is to be a writer and to share her wisdom through the written word? So we began with that. We began with that character of Clare played by Kathryn Hahn, who is me, in that she and I have a lot of the same formative experiences, and yet in her adult life, she took a very different path than me, so she’s very much a fictional character as well.

What was it like to develop a character who is sort of you, but not quite?

Developing the character of Clare was actually developing two characters. We have the adult Clare, who’s Kathryn Hahn, who’s married and has a teenager and a job and always wanted to be a writer and actually had some early promise as a writer, published a bit in her 20s, but then never followed through on it because life took over. And then we have the younger version of Clare played by Sarah Pidgeon. Sarah Pidgeon really enacts in her scenes Clare in her teens and in early 20s, and those scenes are really my story. 

Many of the stories that you see that I tell in “Tiny Beautiful Things,” I said to Liz and the writers in the room it was really important to me that those formative experiences I had in my youth and childhood were the things that in so many ways inform Clare, Kathryn’s character.

I lost my mom to cancer very suddenly when she was 45. I grew up poor and working class in a rural environment. I have a father who was abusive and from whom I’ve been estranged for years. I got married in my 20s, insanely young. I was 19 when I got married, which just makes me think, “What was I thinking?” And divorced by the time I was 25. So those things are all behind Kathryn’s Clare in the form of Sarah Pidgeon. So there’s the autobiography, and then Clare took a different path than me, and so it’s both deep autobiography and deep fiction.

We meet Clare at a really difficult time in her life. Her relationship with her husband is in trouble, her teenage daughter hates her guts, and she’s not doing the thing that she loves to do, which is writing, and she’s trying so hard. She is well-intentioned, but life is a mess. What do you think that says about Clare and then the rest of us?

Well, I think what it says about Clare is, “Welcome to being 49,” or being middle-aged. One of the things that I always have tried to write about as Sugar, you see it everywhere in “Tiny Beautiful Things,” is I’m always saying, “Our work here is not to be perfect. Our work here is to evolve and not just once.” I think that so many of us, maybe because it gives us a sense of safety or false security, we think, “OK, in your 20s that’s the decade where you’re like, ‘Who am I? Should I go here or there? Should I be in this relationship or that relationship? Which path should I take?'” There’s a sense that in your 20s you do a lot of stuff, get lost, go down some wrong paths, but eventually you find your path and then you’re set for life. And of course, that’s not true.

I love the opportunity in this show that we get to say, “OK, she did choose her path in her 20s and she followed it and it worked out pretty well. And now look, she’s at this other moment in her life where it’s time for her to evolve again.” Her teenage daughter who, as you say, hates her, like every teenage daughter on the planet. I mean, having my own 17-year-old teenage daughter, I can tell you they absolutely love you too. Sometimes it’s buried. I mean, all of that, the love and the turmoil, that separating from the parent stuff, all of that is so natural and normal. There’s so much love between them, but there is that conflict.

As we see that, what Clare is realizing is her life has to evolve and change in this next chapter as her daughter is going to be leaving home soon. And a lot of people, they reexamine their lives during that point, so it was really a pleasure to get to tell a story about a woman who is my contemporary – I’m 54, and going through so many of the same things that Clare is going through on the screen – to really tell a complicated story that was about all the beautiful mess of life.

In the introduction to “Tiny Beautiful Things,” Steve Almond writes something like, “One reads Sugar with tears in their eyes.” And I will tell you, one watches Sugar with tears in their eyes as well. I cried almost every episode. Why do you think your work is so emotional?

I love to make people cry, so thank you, Olivia. It’s really one of my favorite things. I think that it’s emotional. And I want to say too about that crying, I’m going to guess that sometimes you cried because something was sad, but a lot of times you cried because something was beautiful. I think that that’s what I most strive to do. 

The truth is beautiful. The complicated, contradictory, raw, real truth is emotional and it opens our hearts. I think that when we see people being vulnerable or living vulnerably or speaking vulnerably something inside of us opens up. And I think that that’s really the mission of art. It is to tell us who we are as humans, and not just who we are, but who are we really? That is everything I always wanted to do, and I love that in this show, I think it asks those same questions.

Your work, even when it’s dealing with the saddest parts and just the most heartbreaking stories, it makes us feel human and more connected. Is that also something you strive to do?

That’s what I do. That’s what I strive to do. Really, what do I want to do with my writing? I want to make people feel less alone. And because I know that literature and television and film — all art forms really — have the power to do that, that’s why I love art of all forms, because I say, “Oh, yes, this is what it does feel like to grieve,” or, “This is what it does feel like to love,” or, “This is what it feels like to be jealous or to have a sense of longing.” All of those emotions that we experience in a really particular individual way are actually universal experiences. And so when you do write a show or a book, that other people say, “Oh yes, me too,” I mean, that’s my whole intention and dream.

This book is 10 years old. What is your relationship to the work that you created that long ago? How have these essays changed for you?

It was published first now almost 11 years ago. It’s been reissued. There’s a 10th anniversary edition that’s out with a new introduction and some new columns in it as well. When I was choosing the new columns to add, I went back and read the book for the first time, honestly, in probably a decade. I was struck by, again, really, we all have the same problems throughout all time. That’s so fascinating to me. Somebody could have written to me 12 years ago about infidelity, and that problem hasn’t changed. The truth, the core truths about how we address any one of these struggles has remained the same.

Always as a writer, you could go back and say, “Well, I would’ve tweaked that sentence,” but I never would’ve changed the core advice in any of the columns, which, whew, was a relief to me because I would hate to be like, “Whoops, I shouldn’t have said that.” It really was a wonderful experience for me to say that this advice is still relevant now.

The show makes a point that being broken is a beautiful place to start, but I also think that when we think about seeking advice, we want to go to the experts, whatever that means. What do you want people to take away from watching Clare’s story?

I first want to say about that expert thing, I think that wisdom comes from so many different sources, and that’s where we should seek advice, from all of the sources, from the therapist and the “experts” who have been trained in psychology and emotional well-being. But we all know, too, that sometimes there’s nothing like a conversation with a friend who says, “I know you and I love you, and I see you, and this is what I think you should do,” or a beloved family member.

Or sometimes it’s just a stranger actually having an interaction with you that blows you away because you’re awakened to something or an advice columnist who you write and say, “Here’s what I can’t say to anyone else, and I’m going to tell you because it’s anonymous and you can answer me.” I think that all of those sources are the ways that we seek wisdom and learn how to thrive. 

You don’t have to be an expert to contribute. You don’t have to be an expert to say, “I have something to say that might be of use.” If you speak from your truest voice, by which I mean the deepest one, the most vulnerable one, the one that’s willing to risk vulnerability, say the scary thing that you feel or that you know, if you speak from that voice, almost always, it’s going to ring a bell in the hearts of other people because they will say, “I recognize you. I know what you’re saying. I believe you because I feel it too.” And I hope that people take that from the show.

Broken is a beautiful place to begin. And what I want to say is most of us are broken, most of us are. I mean, I don’t know a perfect person. What I love about myself and so many others are really the ways that we can both be perfect and imperfect at the same time, that we can have messy lives that are falling apart in some ways and also have so much courage and strength and wisdom, and that we all have something to offer wherever we are on that spectrum.

And it’s also interesting to see how much Clare gets out of being Sugar, and presumably how much you got out of being Sugar, in those early days. Was that how it was for you?

For sure. I wouldn’t say that when I began writing the column, I felt like my life is falling apart. I don’t share that aspect with this character. But I will say there was no question whatsoever that writing the “Dear Sugar” column has made me a better person because I have been forced to reflect on so many people’s problems now. I still am.

Once a month, I write another “Dear Sugar” column, and I’m still constantly thinking, “Well, how can I help this person who’s asking a question about . . .?” Fill in the blank. I have to search my own soul to answer it. I have to examine my own life. And a question I often ask myself when I give people advice, I think, “Am I doing that? Am I taking my own advice?” And I can tell you this, I would be a better person if I did. It forces me to be more contemplative about my own life as well as the lives of others.

You’re still a writer, but now you’re also a podcaster and a producer. You made this show with Reese Witherspoon’s production company, Hello Sunshine, which is all about telling women’s stories. How has your career changed over the years? And what does success mean to you now?

The meaning of success has remained unchanged for me for a long time now. Way back in my 30s when I was trying to finish my first novel, “Torch,” and I felt like I couldn’t do it, I couldn’t do it, I couldn’t be successful. I realized that I was going to have to change my definition of success. To me, it’s this, can I answer yes to these two questions? “Did I do what I said I would do? Did I make good on my intentions? And did I do it to the very, very best of my abilities? Did I hold myself to a rigorous standard?” If I can say yes, and yes, I succeeded.

I think this translates to every profession, but certainly when you’re writing a book, if the measure of success was going to be that it’s published or that it’s a bestseller or that it wins a national book award or it gets adapted into a TV show, you can’t base success on that because that’s all so much outside of my power. What’s in my power is me doing my work and doing it well. That, to me, is my measure of success for sure. 

Now, when it comes to my career, what’s happened is it’s expanded in beautiful and surprising ways because I have held true to what I just said. I held true to doing the work, doing the work to the best of my abilities, to the best of my abilities, over and over and over and over again. And then every time, because of that, an opportunity came up. I said yes and I followed the path down all of these wild directions that took me here to you. I mean, if you think that I had any inkling that this “Dear Sugar” column that I said yes to, that I was paid nothing for, and that I wrote anonymously, would end up being a book, let alone a TV show, I would’ve said you’re fooling me because it can’t be true. And yet here we are.

It’s such a good reminder of the long game too, especially thinking about this show where we see young Clare who wants to be a writer right then and there and then considering how long these things actually take. But like you said, it’s so simple, the two questions you have to answer.

That’s one of the sweetest parts of the show to me, those young moments where young Clare is finding her way into her writing and then when we see adult Clare stepping back into her writing. I find that very moving because it is really important to learn how to keep faith with yourself and believe in yourself because no one else is going to believe in you quite the way you believe in yourself when you’re writing. I love that that’s reenacted, that that’s captured very much in the show.

“Tiny Beautiful Things” is streaming on Hulu.