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Oprah Winfrey
American host and television producer, Oprah Winfrey

Cheryl Strayed and Oprah on the Conversation That Could Change Your Life | Super Soul Sparks | OWN

📅 Oct 18, 2026 OWN 10 MIN 104 VIEWS 48 SEGMENTS · 2 SPEAKERS
Oprah sits down with Cheryl Strayed to explore how loss can become a catalyst for transformation, leading us toward greater compassion, courage, and self-acceptance. Full Podcast Episode: https://podcasts.apple.com/us/podcast... #SuperSoulSparks #ShirleyMacLaine #OprahWinfrey After losing her mother and feeling completely lost, Cheryl Strayed embarked on a journey that would change her life forever. In this powerful conversation with Oprah, the bestselling author of “Wild”, “Tiny Beautiful Things”, and “Brave Enough” shares profound lessons on grief, courage, vulnerability, healing, purpos...

Questions asked in this interview

1
  1. 5:31And I think that sometimes you learn things the hard way and you never forget it, do you?
Oprah Winfrey 0:01 ↗
Hey, sweetie. Look at you. You and your wild boots.
Cheryl Strayed 0:06 ↗
I'm wearing my wild boots, and your honor.
Oprah Winfrey 0:09 ↗
Cheryl Strayed's best-selling book Wild captivated millions of readers and inspired an Oscar-nominated film. But, in a twist Cheryl never even predicted, many of her words have sparked an internet phenomenon.
Cheryl Strayed 0:24 ↗
When people take a quote, they're making it their own. You know, I wrote it, but it belongs to them.
Oprah Winfrey 0:30 ↗
Four years after the enormous success of Wild, Cheryl's powerful, deeply personal quotes are some of the most shared, tweeted, and memed on social media. Cheryl calls quotes mini instruction manuals for the soul. They are the heart of her latest best-seller, Brave Enough.
Cheryl Strayed 0:48 ↗
Quotes, at their core, almost always shout Yes!
Oprah Winfrey 0:55 ↗
Cheryl's memoir details her harrowing 1,100 mile trek on the Pacific Crest Trail. Her quest to reclaim her shattered life after her mother's death resonated deeply with readers.
I said, I have to bring back the book club, because I can't keep it to myself. I just can't keep it to myself. I need to shout from a mountaintop. I need to shout on the web. I need to tell everybody I know about this book.
Four months after Wild was published, Cheryl released another best-seller called Tiny Beautiful Things. It's a compilation of the popular online advice columns she wrote under the pen name Sugar. Cheryl's willingness to reveal her own struggles in order to help her readers won her a passionate and devoted following. With Brave Enough, Cheryl honors that connection by collecting the quotes her legions of readers told her they found most inspiring.
During this whole process of writing, did you change the way you were able to express suffering? Because I had read that at one point that you thought that that was like, don't tell that story. And now you feel completely different. That in the sharing of the story...
Cheryl Strayed 2:15 ↗
Yeah. Well, I would say that that's the lesson, you know, one of the most important lessons I learned through the success of Wild is that it was such an affirmation that if you take that risk, if you take that chance, if you tell that the truest, hardest, deepest story you have within you, you're not going to step into the light and find that you're there alone. That you're going to be surrounded by people who are there with you and say, me too.
Oprah Winfrey 2:40 ↗
And when you take that, essentially you're risking vulnerability, you're risking showing your truest nature.
Cheryl Strayed 2:46 ↗
And you know, here I was writing about the death of my mother. You know, as you know, my mom died of cancer when she was 45. It was the greatest loss of my life. And it was that story that I had to tell over and over again. I've told it in all of my books. And there was a point where I felt like, okay, Cheryl, you need to shut up about this. This is, you know, a lot of people die of cancer. Quit complaining about it. Quit moaning about it.
But I had something really true to tell about that loss. And also what came after that loss. That me finding my way back to life through remembering the love that my mother gave me. And I ended up when I did take that chance of telling that very specific story, speaking with the universal voice. That's what I found. Cuz I wasn't just talking about myself. I was talking about all the people. And people around the world, not just here in the US. That's been astounding to me.
I went to India and I was giving this reading in this packed room in Jaipur, India. This tent at the Jaipur Literary Festival. Hundreds of people. And I looked out and I thought I was terrified and I just thought I'm going to do what I do and I finished my talk and I went and sat at my little table where I was to do my book signing and those hundreds of people all lined up and they all said to me all the same things that people say to me in Ohio and Los Angeles and you know all of that. Exactly. The same things. And again, you know, we are more the same than we are different.
Oprah Winfrey 4:24 ↗
Do you think that every person has that truth within them to speak whether they can write it or not?
Cheryl Strayed 4:34 ↗
I do. I do. I mean, obviously, you know, the work I do is as a writer, but the life I have is as a human. I think that every time you take that, that you find that strength to show your true self. You know, risk showing that self that makes you feel a little uncomfortable, a little like you might be, you know, found out to be the weird one after all. That almost always when I take that chance, whether it be in small talk or in a book...
Oprah Winfrey 5:04 ↗
Well, not just risk, be brave enough to break your own heart, which is your quote.
Cheryl Strayed 5:11 ↗
That's my quote. And what that's about is being brave enough to risk intimacy, to risk rejection, to risk failure. And all of the best things come when you do that.
Oprah Winfrey 5:22 ↗
Because it's about really when you risk all of those things, you are really daring to be more human.
Cheryl Strayed 5:31 ↗
You are. You are. And I think that sometimes you learn things the hard way and you never forget it, do you? Never ever ever forget it. Being brave enough to break your own heart is about being brave enough to make the decisions that end up being really right for you. And also brave enough to sometimes make a decision that wasn't the best one in the end, but you learn from it.
Oprah Winfrey 5:52 ↗
Well, there's no decision that you can't learn from.
First of all, can you finish this? I feel the presence of God when...
Cheryl Strayed 6:01 ↗
When I'm in natural, beautiful, wild places.
Oprah Winfrey 6:05 ↗
I experience love when...
Cheryl Strayed 6:10 ↗
I breathe.

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APA

Winfrey, O. (2026, October 18). Cheryl Strayed and Oprah on the Conversation That Could Change Your Life | Super Soul Sparks | OWN [Interview transcript]. OWN. CEOInterviews.AI. https://ceointerviews.ai/interview/3085780/

MLA

Oprah Winfrey. "Cheryl Strayed and Oprah on the Conversation That Could Change Your Life | Super Soul Sparks | OWN." OWN, 18 Oct. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3085780/.

BibTeX
@misc{winfrey2026_3085780,
  author       = {Oprah Winfrey},
  title        = {Cheryl Strayed and Oprah on the Conversation That Could Change Your Life | Super Soul Sparks | OWN},
  howpublished = {Interview transcript, OWN. CEOInterviews.AI},
  year         = {2026},
  month        = {oct},
  url          = {https://ceointerviews.ai/interview/3085780/},
  note         = {Speaker-attributed transcript with timestamps}
}