How to Be Creative Like a Motherf*cker — Cheryl Strayed (#231)

“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.


You can find the transcript of this episode here. Transcripts of all episodes can be found here.

#231: How to Be Creative Like a Motherf*cker -- Cheryl Strayed

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):

#207: Tools of Titans: Brené Brown Distilled and Other Goodies

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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:

Website | Twitter | Facebook | Instagram | Dear Sugar Radio

Show Notes

  • 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]

People Mentioned

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.

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26 Replies to “How to Be Creative Like a Motherf*cker — Cheryl Strayed (#231)”

  1. Wow, I can’t wait to listen to this one. I really loved the last Debbie Millman. I find I am so stuck with where I am in life and I am hoping for some insights in this one. Since I’m really into writing, I think this might be great.

  2. Hi Tim,

    Fabulous interview.

    I vibe with Cheryl; getting love from readers is the most enjoyable aspect of writing, outside of writing itself. For me, it’s blogging and self-publishing but in any case, knowing you inspired someone and helped them dissolve problems or live dreams elicits like the best feeling ever.

    Interesting point too about her not being able to meet readers as her star shined. She gave the greatest gift through the work itself. The connection was established and energy shared through the book. Knowing this helps authors or anybody who reaches a higher profile learn the art of release and surrender.

    Thanks for sharing guys 🙂


  3. never thought of this before but we are literally a society of motherf*ckers


    another fantastic interview, thank you for everything!

  4. By now, I shouldn’t be amazed at how information comes to me at the time I most need it.

    When I flew to Wisconsin from Colorado on March 9th to surprise my mom for her 87th birthday, I planned to catch up with my brother who is 49 and takes care of her. On the 11th, we watched the Badger game and I took a nap. I planned to suggest a family game night and wanted to take some selfies of the three of us. My brother is pretty reserved, but he’s met a ton of celebrities as a sound technician and wanted to ask him questions to draw him out. He can be hilarious.

    I went downstairs to take the dog for a walk before dinner. When I returned to the kitchen, he had already left. I worked on a blog post when he burst in the back door. He’s a high energy guy.

    “I just missed you,” I said.

    “Yep,” he said and went upstairs to his apartment on the back of my mom’s Victorian.

    He sat down in his chair in front of his computer, clicked on “Inspiring Stories for Women’s History Month and didn’t have time to scroll to the article. He died of a pulmonary embolism. I discovered him and performed CPR and mouth-to-mouth, but he had passed. At first I blamed myself assuming it was a heart attack. But according to experts, that’s very uncomfortable and I found him chilling with both arms relaxed on the armrests.

    To say it was a shock would be an understatement. I blacked out part of the night. My time frame was all mixed up.

    It’s been more than traumatic, but Cheryl’s description of what she went through helped. I’ve gone through breast cancer. I know what it’s like to face death. But I had no idea a healthy person could throw a clot and die instantly. It could happen to anyone. Like her, I’m struck by the fragility of life and wonder with such an optimistic outlook about life, how this will affect me in the years to come.

    Thanks, Cheryl. I needed to know I’m not alone and that I will get through the grieving. Hopefully, without killing him over and over again in my dreams.

  5. The interview made me want to go motherf*ck everything in my life, in a good way 🙂 Awesome interview, as always. Thank you both.

  6. “Like with anything, writing and life,

    You have to do it in a way that works for you.”

    Huge thank you Tim and Cheryl for making this one happen!

    Needed it!

  7. Your podcasts really helped me the past three months in that I recognize so much of how I operate in much of the same way. You just are at the top of your game in comparison. Go do some weird art shit instead of pranks. Those are played out. Thanks for the insightful distractions today. I needed to be reminded to go paint like a mother fucker and the drunk saki one also entertaining. I have this big built up project looming so perfect timing. Thanks for finding so many badass inspirational people, especially the females like Cheryl. ;P We have windmills you can rent for a podcast in the Netherlands. As far as urine, it’s more alluring as fertilizer for the garden than actually sipping it. #ugawtballz

  8. Thank you for interviewing these amazing and courageous women. Their perspectives are life changing and you’re doing a great service to humanity at large.

  9. I loved hearing about the process of a writer, and how writing every single day doesn’t work for everybody. Always great to get an insight into the reasons people write and how they accomplish finishing their projects.

  10. Nice interview, especially if you’re into writing. Hate to say, though, that Cheryl lost some credibility with me when she mentioned astrology a couple of times.

  11. I have often used Cheryl’s “lists of lists” technique in software development, but she makes a great point that this technique can be used to figure out virtually anything. I’ll start doing that more.

    By the way, for anyone else who enjoys making lists of lists, there’s a free tool called WorkFlowy that is perfect for it.

  12. Really liked the idea of using a talisman when attending/participating an event as a way to trigger memories in the future.

    Her list making technique for making decisions got me to thinking about my own process.

    Last really like her writing prompts but when Tim spoke of another person’s method of overcoming a block by figuring out what makes you angry was very helpful.


  13. Hi – I always appreciate your work and that of the folks you talk with. I teach school – kids who are poor, working class, many who do not have the resources available to me. I wonder if you could talk with people, like Ruby Payne, who work with families who are in poverty – rural or inner city or immigrants or farmworkers – all people who are good, smart, but don’t have the resources – time, money, friends, home, health benefits to enjoy or use some much of what you and your guests (and me and my family) have. This is not criticism, but a true desire to help the kids I work with in new and creative and available ways. My great thanks. I think you will find the work of Ruby Payne to be very interesting.

  14. What a powerful interview. Thank you for sharing such an intimate and revealing dialog. I can’t manage to have many authentic conversations with people in my personal life, as I seem to be surrounded by people controlled by fear. These interviews give me something I can get nowhere else. I will personally consider the writing assignment at the end. Maybe someday I’ll find the courage to share it.

  15. In case this hasn’t been resolved yet, the pronunciation of Anaïs Nin is easy peasy: anna-EAS [EAS-ter] n-EEN [sevent-EEN].

    And thank you for teaching me a hex bar is not a Wiccan watering hole. Evidently I am more likely to be found inside the latter.

  16. The truth is that creative people are different from other people – special, for better or worse, in a way that we’re only beginning to understand. And everything we know about them suggests that they’re creative because they’re different, not that they’re different because they’re creative. It’s a vital distinction.

  17. Hi Tim,

    I had my eyes on the 4 hour workweek for quite sometime. I was hesitant that how this kind of book will be applied to my work ( being a parent ) but finally I couldn’t resist buying it. I must say that after many years, I feel the gloominess of my life started to lift and my heart is just pushing me to contact you in hopes of bright days for me and perhaps for many others who are unaware of life being so simple and beautiful as you introduce it.

    The next thing I really hoped to find was your podcast & blog. Your podcasts including the recent one with Cheryl strayed are life changing.

    The reason I want to get in touch with you is regarding my first job being a mom for my children. And I wanted to work with you to either develop a plan specifically for a mom ( since I feel that my job is never ending and I am having difficulty in compressing my mom work week hours into 4 hours). If I am not too late in the game, and if you haven’t been contacted by someone regarding this topic, will it be convenient for you to perhaps start with email communication?

    Thank you so much for reading my message and I am pleased that your work taught me to take the first step and start trying.


  18. Though the discussion was enjoyable, I didn’t find much useful information. That being said the sandwich bit has changed my life, pure gold.

  19. Please, please, please provide transcripts along with these podcasts! I am interested in so many of them, but do not have the time to just sit and listen to them, and they are all very long. If you want people to benefit from your content, then please provide it in ways that will allow everyone to access it!