Overview of Daily Stoic Podcast — Cheryl Strayed episode
This episode of the Daily Stoic podcast (host Ryan Holiday) features bestselling author Cheryl Strayed (Wild; Tiny Beautiful Things). The conversation explores grief and recovery, courage and vocation, the craft of writing vs. publishing, and how suffering can be transformed into purpose. Strayed weaves personal stories (her mother’s death, her Pacific Crest Trail hike, struggles with addiction and risky behavior) with practical, Stoic-aligned insights about action, agency, and artistic labor.
Main themes & key takeaways
- Becoming is active: character and virtue are verbs. Who you are is formed daily by choices and actions, not only by past identity.
- Courage is cultivated: bravery isn’t a fixed trait; it’s practiced like a muscle—take small fearful acts to build it.
- Control the controllable: focus ambition on the work itself (writing as practice) rather than outcomes (publishing, fame).
- Redefine success: measure success by internal criteria—did you fulfill your intention and give it your all?—not external rewards.
- Grief can be transformative: loss doesn’t disappear but can be carried, honored, and turned into sources of empathy, insight, and renewed purpose.
- Agency after harm: many traumatic events aren’t your fault, but you still have the responsibility (and power) to respond and rebuild.
- Art as portal: literature (and other arts) connects us across time and experience; writing is a way to make others feel less alone.
Notable quotes & memorable lines
- “In our 20s, we’re becoming who we’re going to be, so we might as well not become an asshole.”
- “Writing is in your control. Publishing is not.”
- “Courage is a verb, not a noun—cultivate it.”
- Success questions: “Did I make good on my intentions? Did I give it everything I had?”
- “Not your fault, but it is your responsibility.”
- Cheryl’s hiking mantra: “I am not afraid.” (used when terrified to command the body forward)
Topics discussed (high-level)
- Cheryl Strayed’s backstory: mother’s death, early self-destructive behavior, decision to hike the Pacific Crest Trail (Wild) and how that walk catalyzed recovery.
- Tiny Beautiful Things / Dear Sugar: the power of honest, compassionate advice and being present to others’ suffering.
- Writing craft and process: doubt, humility, apprenticeship, looping music as creative mood-setting, finishing work despite fear.
- The distinction between doing the work (within control) and receiving recognition (outside control).
- Grief and consolation: Stoic parallels (Seneca) and practical approaches to carrying loss—acceptance, bearing sorrow, finding “glimmers.”
- Art/music as unique emotional media: books as portals to interiority, music as concentrated mood.
- Teaching and workshops: Strayed’s approach to cultivating courage and teaching literature (ancient plays, consolation literature).
Practical advice & action items
- For creators: make the work your ambition. Set small daily intentions and judge success by whether you met them and gave your best effort.
- To cultivate courage: practice brave acts incrementally—treat courage like strength training.
- When stuck on a project: “surrender to your mediocrity” — let go of grand outcomes; finish the task to learn and move on.
- For grieving: allow wallowing; sit with contradictory truths (pain now + eventual endurance). Look for the “glimmer” or lesson without invalidating real sorrow.
- Reading/wisdom practice: explore poetry and literature broadly—wandering a bookstore or library can change you; treat books as portals to conversation with the past and other minds.
- Writing prompt: “Write what you were really thinking” — aim for interior truth.
Recommended resources mentioned
- Cheryl Strayed books: Wild; Tiny Beautiful Things (Dear Sugar); Torch; Brave Enough.
- Cheryl’s website / Instagram: CherylStrayed.com; @CherylStrayed
- Stoic texts and consolations referenced: Seneca (consolation essays); classical literature (Euripides’ Medea).
- Additional leads: Ryan Holiday’s work (host references), and the Hemingway residency at Ketchum Library (mentioned in passing).
Episode notes
- The episode includes sponsor messages (Toyota, GiveWell, Whole Foods, BetterHelp, Indeed, Eight Sleep, Supercast).
- Tone: intimate, candid, and practical—mixes memoir, instruction, and Stoic-aligned reflections.
- Ideal listener: writers, creatives, people coping with loss or life transitions, and anyone interested in practical philosophy applied to recovery and craft.
If you want a one-line takeaway: focus daily on the character you’re building—do the work you can control, cultivate courage by acting, and carry suffering in a way that deepens your capacity to help yourself and others.