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Cheryl Strayed: “I Had to Lose EVERYTHING to Find Myself”

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Nov 12, 2025

Guest

Cheryl Strayed

Cheryl Strayed, best-selling author of 'Wild' and 'Tiny Beautiful Things', shares her journey of courage and transformation. She discusses how fear accompanies bravery and the importance of acting rather than waiting to feel ready. Cheryl reflects on profound lessons learned while hiking the Pacific Crest Trail, emphasizing the growth that often follows rock-bottom moments. She highlights the role of literature as a means of connection and talks about taking responsibility for one’s life after experiencing loss. This conversation is an insightful exploration of resilience and creative practice.

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Episode notes

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INSIGHT

Courage Is A Practice Not A Trait

Cheryl Strayed argues courage is cultivated like a muscle, not an inherited trait.
She encourages practicing brave acts repeatedly to grow stronger over time.

insights

INSIGHT

Fear And Courage Coexist

Fear and courage sit next to each other; fear enables courage rather than opposing it.
Obstacles like fear often lead to the most meaningful growth and achievement.

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ADVICE

Obsess Over The Work, Not The Outcome

Be fiercely ambitious about the work itself and ignore external measures of success.
Judge success by whether you met your intentions and gave the work your best effort.

Get the Snipd Podcast app to discover more snips from this episode

Why You Might As Well Not Be an Asshole

07:58 • 3min

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Courage Is a Practice, Not a Trait

10:28 • 7min

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Ambition Toward Craft Over Outcome

How External Success Changes the Writing Life

27:13 • 11min

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Books as Portals and the Power of Literature

38:05 • 3min

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Music, Mood, and the Writing Process

40:40 • 3min

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Grief, Consolation, and Writing Through Loss

Making Loss the Start of a New Beginning

49:59 • 9min

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Rebuilding After Loss and the Hero's Journey

58:33 • 7min

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Responsibility After Harm: It's Your Problem to Fix

01:05:15 • 2min

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Writing Residencies and Final Remarks

• Mentioned in 119 episodes

Right Thing, Right Now

Justice in an Unjust World

Ryan Holiday

In 'Right Thing, Right Now', Ryan Holiday argues for the necessity of doing what’s right, even when it isn’t easy. He draws on stories of historical figures such as Marcus Aurelius, Florence Nightingale, Jimmy Carter, Gandhi, and Frederick Douglass to illustrate the importance of justice, kindness, honesty, integrity, and loyalty. The book emphasizes that justice is not an abstract concept but a daily practice that shapes one’s character and impacts those around us. Holiday challenges readers to develop their own moral code and uphold it consistently, providing concrete steps and exercises to help incorporate these values into their lives.

#2366

• Mentioned in 15 episodes

Tiny beautiful things

Cheryl Strayed

This book gathers the best of Cheryl Strayed's 'Dear Sugar' advice columns, initially published on The Rumpus. Strayed, writing under the pseudonym Sugar, provides deeply personal and frank responses to queries on various subjects such as professional jealousy, relationship issues, and coping with loss. The book is rich with humor, insight, and compassion, making it a balm for the challenges of life. It includes never-before-published columns and a new introduction by Steve Almond. Strayed's advice is grounded in her own personal experiences, offering a unique blend of memoir and advice that resonates deeply with readers.

#9329

• Mentioned in 4 episodes

Torch

Cheryl Strayed

#7459

• Mentioned in 5 episodes

Brave Enough

Cheryl Strayed

In 'Brave Enough,' Cheryl Strayed compiles a series of striking and soul-stirring quotes drawn from her various writings. These quotes, each presented on a single page, are designed to inspire and guide readers through life's challenges. The book emphasizes the importance of vulnerability, self-acceptance, and resilience, offering a unique and powerful collection that can be used as a source of encouragement and reflection. Strayed's wisdom encourages readers to confront their fears, embrace their strengths, and live authentically despite life's hardships.

#1402

• Mentioned in 22 episodes

Wild

From Lost to Found on the Pacific Crest Trail

Cheryl Strayed

In 'Wild', Cheryl Strayed recounts her journey hiking the Pacific Crest Trail alone, a trek that spans from the Mojave Desert to Cascade Locks, Oregon. The book chronicles her physical and emotional struggles as she confronts her past, including the death of her mother, the breakdown of her family, and the end of her marriage. Through her experiences with nature, encounters with various people, and reflections on her life, Strayed finds a path to healing and self-discovery. The memoir is known for its vivid descriptions, honest portrayal of grief and personal growth, and the author's unique narrative style that interweaves past and present events.

At some point, you realize courage isn’t something you are born with, it’s something you build. In this episode, Ryan sits down with bestselling author Cheryl Strayed (Tiny Beautiful Things, Wild) to talk about what it really means to be brave. They discuss how fear and courage always show up together, why you can’t wait to “feel ready,” and the difference between saying you’ll change and actually doing it. Cheryl shares what hiking alone on the Pacific Crest Trail taught her about courage, loss, and starting over.

Cheryl Strayed is the author of the #1 New York Times bestseller Wild: From Lost to Found on the Pacific Crest Trail, which was made into an Oscar-nominated film. Her bestselling collection of Dear Sugar columns, Tiny Beautiful Things, was adapted for a Hulu television show and as a play that continues to be staged in theaters nationwide. Strayed's other books are the critically acclaimed novel, Torch, and the bestselling collection Brave Enough, which brings together more than one hundred of her inspiring quotes. Her books have sold more than 5 million copies around the world and have been translated into forty languages

You can grab copies of Wild and Tiny Beautiful Things by Cheryl Strayed at The Painted Porch: https://www.thepaintedporch.com/

Follow Cheryl Strayed on Instagram @CherylStrayed and check out more of her work at her website CherylStrayed.com

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