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10 Quick Questions for Cheryl Strayed

Acclaimed novelist tackles the small screen in Hulu’s ‘Tiny Beautiful Things’


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Robby Klein/Contour by Getty Images

Author Cheryl Strayed’s bestseller Wild, which chronicled her solo hike of the Pacific Crest Trail at age 26, was brought to life on the big screen in the 2014 movie of the same name. Now, you can watch an adaptation of the 54-year-old’s book Tiny Beautiful Things — based on her Dear Sugar advice column — streaming on Hulu. 

How involved are you in the adaptation of Tiny Beautiful Things?

I’m an executive producer and one of the writers. The show runner-creator is the wonderful Liz Tigelaar. She really taught me so much about television writing as we crafted this season. Kathryn Hahn is wonderful as the character Clare. She’s not me. She has her own middle-age problems that aren’t mine, but then her past — those times where she’s remembering — those are very autobiographical. … It’s always a thrill when something you’ve made inspires other artists to make something else, and then to get to be so involved in the process was absolutely just an education. I think of myself as the eternal apprentice, so for me to get to be in the writers room and to say, I’ve been a writer for decades now, but I’ve never written a TV show, and just to be somebody who is always learning new things, I can’t ask for more.

spinner image quentin plair as danny and kathryn hahn as Clare in a still from tiny beautiful things
Strayed is an executive producer and writer for the new Hulu show “Tiny Beautiful Things."
Jessica Brooks/Hulu
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What’s the best advice you’ve ever received, and who was it from?

Of course, my dear mother has influenced my life so deeply. She died when she was 45. So I’ve lived a long time without her, but her legacy lives on in me. … What she would say to me is, “Cheryl, there will always be hard days, there will always be difficult times, but you have the opportunity to put yourself in the way of beauty every day. And it’s up to you to find, essentially, the beauty and the joy in life.” She would say, “There’s always a sunset, there’s always a sunrise, and it’s up to you to be there for it.” Obviously, I thought about that on the Pacific Coast Trail, and in a larger sense of my work as Dear Sugar. That idea of putting yourself in the way of beauty is core to so much of the advice I give, because no matter what your problem is, your struggle or your loss, at the end of the day, you do have to find a way to find that lightness in the darkness, to find the courage, the strength to go forward, even if it hurts. It’s a kind of core optimism that my mother had that I absolutely know lives inside of me.

And the worst advice?

It’s funny, my mom gave me the best advice; my grandmother, who is dead now, my mother’s mother [gave me the worst]. When I was a teenager … she said, “Never, never be entirely naked in front of your husband. Always keep a shirt on.” Even then as a teenager, I thought, This is terrible advice. This does not make for a good marriage. It was not the marriage advice I would give.

Back in 2012, when Wild was picked as an Oprah Book Club selection, it clearly changed your life. Did Oprah give you any advice?

Oh, Oprah’s given me so much great advice. She’s a really good friend. We had really good conversations about a number of things when Wild was really successful — about stepping into that kind of fame, the public stage if you will. She’s given me advice on just everything. … I used to do a Dear Sugar podcast. Steve Almond, my cohost, and I had Oprah on the show. We expanded it into two episodes. She was so good. It’s all about how to say “no.” … As you know, Oprah has endured a lot of hard things. She had a traumatic childhood. She had a lot of stuff to live through, [but she says that] the hardest journey of her life was learning how to say “no.” I was just like, so many people are going to relate to that. I know what she’s talking about. That word is not a word that a lot of us come to easily.

What would you tell your son or daughter if he or she wanted to hike the PCT alone?

I would want them to do it. I would be scared, but I would be thrilled for them to do it, because I know what an enriching growth opportunity it would be, how good it is for all of us when we venture into the wilderness and see what we can find about ourselves. All of us, when we venture into the world and do something hard physically, everything about it is good. Yes, I would want to put some kind of computer chip [in them] so I could track them. Yeah, I would worry. But of course, we worry in a different way about the kids who are just scrolling around on their phones. I think we have this funny, strange idea about danger. I think the most dangerous thing is not venturing into the wilderness. The most dangerous thing is not addressing your addiction on social media or not putting your phone down and seeing the world as it is just with your own two eyes and wandering it on your own two feet.

Would you go on another adventure like that again?

Oh yeah. I’m a person who loves to travel. I’ve become really very much conscious — I always felt this inside myself —  it’s really important to have rites of passage, journeys. And not just the sort I took in my 20s where I really think, in so many ways, I was trying to figure out who I was and trying to become and live in the world without my mom and step into my real adulthood. I sense something like that coming again in my future. My kids are 17 and 18. I’m 54. I’m like,OK, whatever this next era of my life is … what's it going to be? Travel has always helped me see things more clearly and deeply. Especially the kind of travel where you’re walking through the wilderness, but travel of all varieties has done that. I love to hit the road and travel a lot.

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Where do you think you’ll go next?

That’s always the problem, right? There are so many things to see. One of the theories of travel that I come up against is: Is it better to go to new places that you’ve never seen or return to the place that you love? I fell madly in love with New Zealand. In 2017, my husband and I and our two kids went to New Zealand and hiked the Routeburn Track and Milford Track. I could live in this country. If it wasn’t so dang far away from the U.S., I would be there in a minute. So I’d love to return and explore it. But I’ve also never been to Finland. I grew up being told that I had a lot of Swedish in my background, and then I did those DNA tests, and they were like, no, you are a little bit Swedish, but you are Finnish. … So I’d love to go explore Finland and Scandinavia. I’m really drawn to that part of the world. I want to go hiking in Japan. I’ve been to Japan very briefly. But here’s the thing: You asked the question, “Where would I go?” Where wouldn’t I want to go? I have a hunger for the world, and I always have.

What’s on your reading list?

spinner image tiny beautiful things book cover with small sugar cube printed on cover, along with words soon to be a hulu original series, cheryl strayed, bestselling author of wild, tiny beautiful things, advice from dear sugar with new material
“Tiny Beautiful Things” is a collection of essays compiled from Strayed's “Dear Sugar” advice column, which she originally wrote anonymously.
Vintage Books

I just finished a book, a memoir by Laurel Braitman. It’s called What Looks Like Bravery, and it’s just a beautiful memoir about a woman — the subtitle is An Epic Journey Through Loss to Love. She lost her father when she was a teenager. It’s really about her journey as an adult reckoning with that loss, and then later when she was an adult, her mother dying. She’s just a very compassionate, honest, searching soul, and I was utterly absorbed in it. I highly recommend it. She’s a really fascinating woman.

You’ve just become a TV writer, but are you a TV watcher?

Oh my God, yes. As a teenager, I didn’t have electricity. In my 20s and well into my 30s, I didn’t have a TV. I really missed a lot of TV. I usually binge. I cannot bear it anymore when I have to have the episodes doled out. The best thing I’ve watched recently is this show called Slow Horses on Apple TV+. It’s a thriller set in London, and Gary Oldman stars, and it was one of the shows where the first episode, I was like, I don’t know? I’m not sure? Then I kept watching, and I was all in. Of course, I was addicted to Succession, as everyone else is. … Bad Sisters. Right now my husband and I, we’re doing The Last of Us on HBO. It’s really good. I also must confess that through all the raising teenagers in the pandemic and online school, my husband and I’d get to the end of day, [and] we’d need gentle television — something that’s going to make us feel peaceful. So we are huge Masterpiece PBS show [watchers]. 

What’s different at 54 than when you were younger?

All of the usual stuff. We do get wiser. The thing I love about this age is that you have perspective. Even if times are difficult, you usually can get through them, and something good will rise from it. I would say the shift that’s going on in me now is the heightened awareness of being a little past the middle of things. I feel like I’m still so much in my prime at 54, and I have so much writing I want to do, work I want to do, trips I want to take, experiences I want to have. And yet also feeling like looking ahead, it’s not the same. In your 20s and 30s, you’d look ahead and it was all questions: Who will I marry? Will I have kids? Where will I live? Now some of those really big life questions have been answered. ... Now I’m stepping into this age where I get to have the freedom and liberation that we get to have after we’ve raised our kids, after we’ve staked out claims professionally or whatever it is. I’m just sort of going ahead with a sense of curiosity and openness and adventure.

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