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Living with Grief, Bravery, and Empathy: An Interview with Cheryl Strayed

11 May, 2019 | Posted by Kate Green Tripp

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Living with Grief, Bravery, and Empathy: An Interview with Cheryl Strayed
Cheryl Strayed is the widely acclaimed author of the #1 New York Times best-selling memoir Wild: From Lost to Found on the Pacific Crest Trail, the New York Times best sellers Tiny Beautiful Things: Advice on Love and Life from Dear Sugar and Brave Enough, as well as the novel TorchWild was chosen by Oprah Winfrey as her first selection for Oprah's Book Club 2.0 and adapted into an Academy Award-nominated movie.
Cheryl's books have been translated into 40 languages, and her essays have been featured in numerous publications, including The Best American EssaysNew York TimesWashington Post MagazineVogue, and Salon. She is cohost, along with Steve Almond, of the WBUR / New York Times podcast Dear Sugars, which originated with her popular Dear Sugar advice column on
Cheryl Strayed, MFA, will be teaching Brave Magic: An Invitation to Curiosity, Creativity, and Courage with Elizabeth Gilbert on September 20 – 23, 2018 at 1440 Multiversity.

1440: You are known (and adored) for your grit and honesty as a writer and as the voice of Sugar. Why do you think readers and listeners are so hungry for both?

Cheryl Strayed: We all struggle. We all experience self-doubt. We all want love and fear we won't get it. As a writer and as a person, I've always tried to reveal rather than conceal those very human realities. I think people are hungry for it because it's in opposition to the happy face so many people feel like they should be showing to the world. There's nothing wrong with saying "Everything is great!" when everything is great, but the fact is that we all suffer, we all make mistakes, and we all have fears and insecurities.
I think people feel a tremendous sense of comfort when those around them are willing to tell the complicated truths of their lives, rather than just one part of them.
By telling stories about the darker, harder parts of my life—and via my work as Sugar, the lives of others—I hold up a mirror. People recognize themselves. They understand they are not alone.

1440: As Sugar, you offer people what has been described as radical empathy. What does this concept mean to you? Do you practice radical empathy toward yourself? What does that look like?

Cheryl Strayed: To me, radical empathy means striving to always hold others in unconditional positive regard. It means assuming that most of us are essentially good at our core, that we are all worthy of love and forgiveness. In action, it means willingness to contemplate the decisions and actions of others with consideration rather than condemnation, with compassion rather than scorn. Having radical empathy is not about letting people off the hook for their misdeeds and mistakes, but rather holding them—and ourselves—to a higher standard. It's about saying, "I believe we are capable of doing better, of being kinder, braver, more honest, and more generous—even after we have failed to do so."
I do a fair job of radical empathy towards myself, but I could do better! When I start beating myself up about something I wish I'd done or not done, I try to imagine what I might say to a friend if he or she came to me with that same struggle. It's so much easier to be kind to others than it is to be kind to ourselves, so that mental shift in perspective helps me get out of my head a bit. Another thing that helps me when it comes to self-empathy is trusting the truth that we learn from our mistakes—that even if I have done something I regret, I have the opportunity to allow that experience to be a teacher to me so I won't make the same mistake again.
Brave Magic
Elizabeth Gilbert,  Cheryl Strayed
September 20 - 23, 2018
There is still space to register for this program! Learn more about our commuter pass option with local hotel discounts, then call 1 844 544 1440 to book. Spend a one-of-a-kind weekend with Elizabeth Gilbert and Cheryl Strayed exploring the pathways...

1440: Wild is, among other things, a tale of loss and grief. You have written extensively about the damaging ways you responded to both as a young adult. How do you grieve in your life today?

Cheryl Strayed: Every day of my life for more than 26 years has been imbued with the sorrow that my mother is no longer in it. My grief is present in every breath I take—which doesn't mean I'm always sad. It means I've had to get used to living with that enormous loss. I've had to learn to carry it with me and I've done that, rather joyfully.
The deepest thing I know about loss is that grief is love. It is love. It is not sorrow. It is beauty, not ugliness.
Maybe once or twice a year, I will think of my mom and weep. I miss her. But I bring her back to me every day in my own mothering of my two children and in my work. She is alive in my stories.

1440: You encourage aspiring writers to be brave in the topics they explore in their work. Why is bravery so critical to the creative process?

Cheryl Strayed: Because the creative process is ultimately about telling the truth. It's about being as transparent as we can possibly bear to be. That is inherently scary. We risk condemnation, rejection, and vulnerable exposure when we show the world who we really are inside. You have to be brave to do that and if you aren't able to muster that bravery, it is pretty difficult to make art. Art's job is to tell us what it means to be human, so the people who create it need to be up to that task.

1440: What obstructs your own bravery? In writing and in life? How do you respond?

Cheryl Strayed: Like anyone, what I want most of all is to be loved and praised and I also want my books to be loved and praised. And yet I know there is no such person who can only be loved and praised, and also no such book. So, I remind myself of that when I feel afraid as a writer. I remind myself that my truest intention isn't to please people. My intention is to do my work. So I do it. And you know what? The writing that people love me the very most for is precisely the writing I felt the very most afraid to write. In the hard moments, I remember that.
This interview was conducted by Kate Green Tripp, Managing Editor for 1440 Multiversity.

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