“One of the scariest things in our lives is actually doing what we know we want to do.”
– Cheryl Strayed
If you’re interested in the creative process of a famed author, jumpstarting your own creation, note taking, list making, or simply handling hard emotions, this episode is for you. Recorded in front of a 2,000-plus person crowd at SXSW in Austin, Texas, this one was a blast.
My guest is Cheryl Strayed (@CherylStrayed), author of the #1 New York Times bestselling memoir Wild, the New York Times bestsellers Tiny Beautiful Things and Brave Enough, and the novel Torch. Her books have been translated into forty languages around the world. Wild was chosen by Oprah Winfrey as her inaugural selection for Oprah’s Book Club 2.0 and was made into an Oscar-nominated film starring Reese Witherspoon and Laura Dern.
Strayed’s essays have been published in The Best American Essays, The New York Times, The Washington Post Magazine, Vogue, Salon, The Sun, Tin House, and elsewhere. Strayed is the co-host, along with Steve Almond, of the WBUR podcast Dear Sugar Radio, which originated with her popular Dear Sugar advice column. She lives in Portland, Oregon.
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Want to hear another podcast with a bestselling author? — Listen to my interview with Brené Brown. In this episode, we discuss vulnerability, schools of philosophy, and creating a home run TED Talk (stream below or right-click here to download):
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QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.
Scroll below for links and show notes…
Selected Links from the Episode
- Connect with Cheryl Strayed:
- Wild: From Lost to Found on the Pacific Crest Trail by Cheryl Strayed
- Wild (the movie with Reese Witherspoon and Laura Dern)
- Tiny Beautiful Things: Advice on Love and Life from Dear Sugar by Cheryl Strayed
- Brave Enough by Cheryl Strayed
- Torch by Cheryl Strayed
- Johnny Got His Gun by Dalton Trumbo
- Cheryl’s Dear Sugar advice column
- Dear Sugar, the Rumpus Advice Column #48: Write Like a Motherfucker
- The 4-Hour Chef: The Simple Path to Cooking Like a Pro, Learning Anything, and Living the Good Life by Timothy Ferriss
- The ‘Painful Personal Toll Lung Cancer Has Taken on My Life’ by Cheryl Strayed, The Huffington Post
- Memento mori: “Remember that you must die.”
- Death Over Dinner
- The Pacific Crest Trail
- Citizen: An American Lyric by Claudia Rankine
- Lives of Girls and Women: A Novel by Alice Munro
- New and Selected Poems, Volume One by Mary Oliver
- The Life-Changing Magic of Tidying Up: The Japanese Art of Decluttering and Organizing by Marie Kondo
- Oprah Meets Cheryl Strayed for the First Time, Oprah Winfrey Network
- Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers by Tim Ferriss
- A listener asks Cheryl: “What’s it like to know Tiny Beautiful Things saved lives — including mine?” [07:09]
- Books are Cheryl’s religion. [08:27]
- Cheryl describes her necklace and its significance. [12:29]
- As a mother, how does Cheryl balance the need to nurture a sense of security for her children while encouraging them to go on their own quests of self-discovery? [14:17]
- Quotes that have most resonated with readers and fans. [17:05]
- Write like a motherfucker. [19:28]
- Associating words like humility, acceptance, and surrender with strength and power. [20:21]
- What is Cheryl’s writing process? [22:37]
- As a self-described “binge” writer, what does a day blocked for writing look like? [26:41]
- Writing from personal experiences can dig up painful memories, but so does therapy. [31:26]
- Prompts Cheryl has found to produce the most interesting writing from her students. [36:26]
- Mechanisms, tricks, or habits Cheryl uses if she’s obstructed by writer’s block. [38:33]
- Cheryl has said she thinks of mortality daily. What triggers these thoughts, and what do they motivate her to do — or prevent her from doing? [41:12]
- On coping with her mother’s death and recognizing mortality as an inevitability rather than a tragedy. [46:22]
- What was Cheryl’s process for answering questions for her Dear Sugar columns, and did she ever get questions she didn’t feel equipped to answer? [48:52]
- Helping someone in need process an unanswerable question. [50:53]
- Overcoming a difficult challenge — and uncovering clear truths — by making a list. [52:15]
- The generosity of doing what we want to do. [56:02]
- Cheryl is known for giving advice; who does she reach out to when she needs answers? [1:01:04]
- On marriage: why did Cheryl stray? [1:05:05]
- What would Cheryl say to someone hiking the Pacific Crest Trail today? [1:06:59]
- Cheryl believes in restrospective fun — it’s the terrible things that happen when traveling that make the best stories for later. [1:08:13]
- I believe in anticipatory fun — eighty percent of the enjoyment I get is planning and looking forward to travel. [1:10:16]
- One to three books Cheryl would give to graduating students. [1:11:43]
- Who or what comes to mind when Cheryl hears the word “successful?” [1:14:50]
- Something Cheryl is currently trying to improve in her life. [1:16:22]
- A purchase under $100 that had the most positive impact on Cheryl’s life. [1:17:40]
- On the merits of learning by failure in the arts — but what often gets lost in translation. [1:21:08]
- “Surrender to your own mediocrity.” [1:27:12]
- Advice Cheryl would have for someone else whose memoirs were being made into a movie. [1:30:09]
- Cheryl tells us her story about meeting Oprah for the first time. [1:33:13]
- Cheryl closes with a writing project for us. [1:36:06]
- Oprah Winfrey
- Reese Witherspoon
- Laura Dern
- Dalton Trumbo
- Bobbi Strayed Lindstrom
- Carver Strayed Lindstrom
- David Foster Wallace
- Leo Tolstoy
- Po Bronson
- Bobbi Lambrecht
- Marco Littig
- Brian Lindstrom
- Claudia Rankine
- Alice Munro
- Mary Oliver
- Nick Hornby
- Ronald Nyland
The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.