The Daily Stoic Podcast

Episode: "Cheryl Strayed: 'I Had to Lose EVERYTHING to Find Myself'"

Date: November 12, 2025
Host: Ryan Holiday, with Stephen Hanselman
Guest: Cheryl Strayed (Author, “Wild,” “Tiny Beautiful Things”)

Episode Overview

In this rich and candid conversation, Ryan Holiday and Stephen Hanselman welcome bestselling author Cheryl Strayed to discuss the transformative journey of loss, courage, writing, and self-discovery. Drawing on her personal experiences—losing her mother young, the dissolution of her marriage, and her famous solo trek on the Pacific Crest Trail—Cheryl delves into how life's lowest moments can offer the greatest opportunities for growth and renewal. The discussion ranges from the Stoic approach to virtue, the craft and meaning of writing, the paradox of courage and fear, the process of grief, and ultimately, finding light in the darkest moments.

Key Discussion Points & Insights

The Ongoing Journey of Becoming (08:42–11:56)

• Growth in Adulthood:
  Cheryl reflects on her own advice, “In your 20s, you're becoming who you're going to be, so you might as well not be an asshole.” She emphasizes that this continual process of growth isn’t just for our 20s—change is always possible.

  “We're constantly evolving and it's always our job to grow... You might as well pretty early on I think make a decision to have character be a really important thing, virtue a very important thing.” (08:55, Cheryl Strayed)

• Learning Through Mistakes:
  Often, our ethical code becomes clear only after we violate or betray it.

  “Very often the way we learn what our ethical code is is that we violate it or we disappoint ourselves…” (09:58, Cheryl Strayed)

Virtue, Courage, and Agency (10:58–16:19)

• Virtue as Action:
  The idea that being good or brave isn’t inherent; it’s something built and lived out daily.

  “Courage is not some...inherent characteristic...It’s literally like the way you lift weights and you get stronger day by day. Courage works like that, too.” (10:58, Cheryl Strayed)

• Humility and Seeking:
  Real wisdom requires humility—the willingness to question oneself, choose the right path daily, and continue seeking meaning, even in small ways.

  “The wisest people I know are...that word humility always comes to mind…” (16:17, Cheryl Strayed)

Writing, Publishing, and Process (17:47–29:54)

• Distinguishing Between Writing and Publishing:
  Cheryl’s famous advice is discussed: being a writer is in your control, but publishing and success are not.

  “Be wildly, profoundly, deeply ambitious about the work itself…that is the only thing you have control of.” (18:57, Cheryl Strayed) “Writing is the part of it that I control. And publishing, being an author, that's for other people...” (17:55, Ryan Holiday)

• Success & Apprenticeship:
  Cheryl describes finding success not in external accolades but in fulfilling her intentions and doing her best. She remains an “apprentice” to her craft, always learning.

  “I never want to stop considering myself an apprentice to the craft and art of writing.” (24:17, Cheryl Strayed)

• Dealing with Doubt:
  Even after best-sellers, the internal landscape for a writer doesn't change: doubt and humility remain.

  “I don’t think you write from a place of arrogance and confidence. I think you write from a place of fear and humility.” (29:44, Cheryl Strayed)

The Transformative Power of Art and Literature (33:02–39:25)

• Connection Across Time and Space:
  The conversation touches on how literature offers a “portal” to other lives, eras, and emotional truths, allowing us to feel less alone.

  “Books are door shaped portals carrying me across oceans and centuries, helping me feel less alone.” (36:54, Stephen Hanselman quotes a poem)

• Unique Power of Different Arts:
  Each art form—writing, music—has emotional strengths; with writing uniquely suited for deep, subjective human experience.

Music, Emotion, and Creativity (40:24–43:36)

• Soundtracks & Emotional Cues:
  Music’s role in creativity and emotion is discussed, with Cheryl sharing how specific songs set the creative tone for her essays.

  “I listened to Beth Orton's song 'Central Reservation' probably...a thousand times...It was a vibe...a tone.” (42:11, Cheryl Strayed)

Grief, Endurance, and Transformation (46:06–56:32)

• Living With Loss:
  Cheryl shares her journey with grief after losing her mother, noting not all pain is “gotten over,” but can be carried and ultimately transformed.

  “It was the worst thing that's ever happened to me. And it has brought me also the most profound, profound gifts...self understanding, compassion for others, empathy...” (53:26, Cheryl Strayed)

• Agency in Suffering:
  Even when events aren’t our fault, we are responsible for our response and our healing.

  “It's not your fault, but it is your responsibility.” (61:53, Cheryl Strayed)

• The Rock Bottom and Renewal:
  Transformation often requires reaching a nadir; afterwards, there is sometimes gratitude—for the strength, perspective, or compassion gained.

Embracing Life’s Contradictions & Stoic Parallels (57:47–65:46)

• Living with Ambiguity:
  Cheryl and the hosts discuss sitting with contradictory feelings—pain and eventual growth—without forcibly skipping to positivity.

  “Let yourself feel all of those emotions…You can’t just hop to that...false sense of optimism and cheer. I think that’s actually really harmful.” (60:34, Cheryl Strayed)

• Finding the Glimmer:
  Even in permanent darkness or loss, there’s a call to seek “glimmers,” however small, of learning or growth.

  “Your job is to find some glimmer in it. It will never not be true that that terrible experience didn't happen to you, but your job is to find the glimmer in it.” (63:30, Cheryl Strayed)

Notable Quotes & Memorable Moments

• “We're always becoming who we're going to be...Character is really something we do as opposed to something we inherently have.”
  — Stephen Hanselman (10:12)

• “You can’t be brave unless you have fear. Fear is such a wonderful opportunity to show us to ourselves what we’re capable of...It’s kind of like the obstacle is the way.”
  — Cheryl Strayed (14:43)

• “Can I answer yes to these two questions: Did I make good on my intentions? And did I give it everything I had? That's success to me.”
  — Cheryl Strayed (19:34)

• “I was finding my way back to my strength, back to my courage...I genuinely believe that we all have within us everything we need, everything we need to survive the hardest things.”
  — Cheryl Strayed (56:32)

• “It's not your fault, but it is your responsibility.”
  — Cheryl Strayed (61:54)

Key Timestamps

| Timestamp | Segment / Topic | |---------------|-------------------------------------------------------| | 08:42 | Becoming (virtue in your 20s and beyond) | | 10:58 | Cultivating courage; virtue as a verb | | 17:47 | Writing vs. publishing; process vs. outcome | | 19:34 | Personal definition of success in writing | | 24:17 | Staying an apprentice; ongoing learning | | 33:02 | The deep, consoling power of books and art | | 36:54 | “Books are door-shaped portals…” (quote) | | 42:11 | Music as creative frequency and emotional prompt | | 46:06 | Carrying grief, endurance, and transformation | | 53:26 | Gifts of suffering and the aftermath of profound loss | | 61:53 | “It’s not your fault, but it is your responsibility” | | 63:30 | Finding glimmers in darkness, lasting trauma/lessons | | 66:20 | Using painful experience to create art for others |

Tone and Style

The conversation is candid, humble, and reflective—equal parts practical wisdom and intimate storytelling. The tone is accessible and direct, blending Stoic philosophy with raw personal narrative. Cheryl’s humility and eloquence offer encouragement without platitudes, and Ryan Holiday and Stephen Hanselman create a thoughtful, philosophical atmosphere, inviting listeners to reflect on their own transformations.

Summary for New Listeners

This episode with Cheryl Strayed is a guide to navigating loss and change with humility, courage, and intentionality. It offers specific wisdom for creatives and for anyone struggling with grief, disappointment, or a feeling of starting over. The hosts and guest revisit classic Stoic truths—virtue is action, agency is everything, what matters is not what happens to us but how we respond—while sharing actionable advice and personal stories. Listeners will come away understanding that life’s greatest lessons and most profound strengths are often found in hardship, and that embracing this reality is the foundation for resilience and enduring meaning.