Podcast Summary
My So-Called Midlife with Reshma Saujani
Episode: Revisit: Embracing Your Crone Age with Cheryl Strayed
Date: April 1, 2026

Main Theme

In this engaging episode, host Reshma Saujani sits down with bestselling author and advice columnist Cheryl Strayed to discuss the realities of midlife—what it means to truly embrace this transitional era, the lessons learned, and the work of letting go, accepting, and finally, living fully. Touching on deep personal stories and hard-earned wisdom, the conversation ranges from grief and transformation to menopause, marriage, infidelity, and the importance of speaking our truths.

Key Discussion Points & Insights

1. Midlife Mindset: Peaks, Valleys, and Acceptance

• No "Best Time" in Life: Cheryl rejects the notion of a single “best” era. Every decade includes both suffering and joy, and growth comes from embracing both.
  • “Every decade of my life has contained real sorrow, real loss, real trauma and real joy, real profound growth and transformation and satisfaction.” – Cheryl Strayed [05:15]
• Acceptance vs. Arrival: The lesson isn’t about getting to a mountaintop but learning to accept the highs and the lows as integral parts of a full life.
  • Memorable Quote: “Our job here is to evolve, and we can't evolve with only suffering, and we can't evolve with only joy.” – Cheryl Strayed [05:44]

2. Menopause and “Crone Age”

• Perimenopause & Menopause: Cheryl details her journey through menopause, using humor and self-reflection, and discusses embracing her new “crone age.”
  • “I call this my crone age. … I downloaded this app called Big Day…and the title I gave that was crone age.” – Cheryl Strayed [09:00]
• Cultural Rites of Passage: She parallels this phase to ancient rites of passage, noting the lack of such rituals in modern society and the need to define our own transitions.

3. Grief and Transformation

• Losing Her Mother: Cheryl discusses profound grief after her mother’s death and the ensuing sense of being lost in her 20s, leading to her journey on the Pacific Crest Trail (as chronicled in Wild).
  • “I knew the wilderness made me feel whole. And so that’s how I came upon this decision to go on this journey.” – Cheryl Strayed [11:58]
• Quarter-Life vs. Midlife Crisis: The deep work of “rising” happened in both her 20s (after loss) and her 50s (raising teens during the pandemic).

4. Lessons in Acceptance

• Let It Be: The capacity for growth lies in acceptance, not resistance.
  • “The last line of Wild—‘How wild it was to let it be’—That is, to me, about acceptance.” – Cheryl Strayed [13:55]
• Advice for Grieving Women: Cheryl encourages being present and using available time to “make whole what doesn't feel whole between you today,” rather than waiting for resolution at a loved one's deathbed.
  • “Be here now and think about the ways that you can make whole what doesn’t feel whole between you today.” – Cheryl Strayed [15:10]

5. Marriage, Infidelity, and Sexual Honesty

• Why Do People Cheat? Both host and guest challenge monogamy myths and the silence around real challenges, stressing a need for honest conversations about sexuality and fidelity.
  • “We’d all be so much better at monogamy if we could just from the get go be like, okay, listen people, this is actually, it’s doable, but it’s challenging you know?” – Cheryl Strayed [20:52]
• Forgiveness and Growth: Cheryl’s own experience of cheating in her first marriage and being cheated on in dating in her current marriage (before marrying) became catalysts for deeper, more honest connections.
  • “It opened up a conversation between us that wasn't about the fairy tale, that was actually about human sexuality and, you know, his wounds and my wounds and our hopes and expectations and aspirations as a couple.” – Cheryl Strayed [23:43]
• Why Women Cheat: Often, women do so to reclaim something “just for them” in a world where they feel depleted.
  • “[Esther Perel] says, you know, because the incidence of women cheating are much higher. And she says it's just oftentimes that women just want something for them.” – Reshma Saujani [25:25]

6. Universal Struggles and Vulnerability

• Dear Sugar’s Five Problems: After years as an advice columnist, Cheryl’s found most letters fall into these categories:
  • Family of origin trauma
  • Sex/romance/marriage concerns
  • Career and life direction
  • Fertility/aging/reproductive issues (“problems with my vagina”)
  • General adult “lifestyle” problems
  • “The struggles we have are so universal…we basically never are [alone].” – Cheryl Strayed [27:23]
• Why Don’t We Share? Because of social training to please and fear rejection—especially acute for women, leading to people-pleasing and “fronting.”
  • “From day one…to be pleasing to others so that they will love us and include us.” – Cheryl Strayed [27:47]
  • “You are part of the equation. And I can't tell you how many years it's taken me to learn that lesson.” – Cheryl Strayed [28:47]
• Importance of Saying It Out Loud: Naming our truths, needs, and even our ages is a “tiny revolution” against shame.
  • “Say who you are and say it out loud.” – Cheryl Strayed [29:50]

7. Success and What Comes Next

• Redefining ‘Making It’: Cheryl’s "I made it" moment came with publishing her first novel, long before international fame with Wild. She reflects on how the dream of creative fulfillment predates success, and success is shared by all women who paved the way.
  • “I made it. Yeah. And I didn’t make it just for me. I made it for all of the ways that they [my female ancestors] sacrificed and suffered and loved and gave and contributed…” – Cheryl Strayed [35:00]
• Looking Ahead: As her children leave home, Cheryl feels another “rite of passage” coming, paralleling her earlier journey and underlining the cycles of evolution throughout life. She intends to write about it.
  • “I could see very clearly that what I had done for myself in my 20s is I gave myself what the culture didn’t give me, that…rite of passage…We need to really think about the other times that we transition.” – Cheryl Strayed [36:00]
• A Privilege to Age: After losing her mother at 45, Cheryl embraces aging with gratitude, reframing middle age as a privilege denied to some.
  • “When you lose your mom at 45, you understand what a privilege it is to get to live into middle age and to get to be old.” – Cheryl Strayed [38:00]

Notable Quotes & Memorable Moments

• On Life’s Highs and Lows:
  “There is no such thing as the best time in your life.” – Cheryl Strayed [05:07]
• On Acceptance:
  “How wild it was to let it be.” – Cheryl Strayed [13:55]
• On Speaking Truth:
  “Say who you are and say it out loud.” – Cheryl Strayed [29:50]
• On Female Friendship & Shared Humanity:
  “The struggles we have are so universal. We always feel like we’re alone, and we basically never are.” – Cheryl Strayed [27:23]
• On Aging:
  “What a privilege it is to get to live into middle age and to get to be old. I hope I get that.” – Cheryl Strayed [38:00]
• On Looking Forward:
  “I could see very clearly that what I had done for myself in my 20s is I gave myself what the culture didn’t give me…a rite of passage.” – Cheryl Strayed [36:00]

Timestamps for Key Segments

• 01:39 — Reshma’s introduction & Cheryl’s story context
• 05:07 — Cheryl on the myth of “the best decade”
• 09:00 — Embracing menopause (“crone age”)
• 10:45 — Coping with grief/loss in 20s, Wild’s origin
• 13:55 — Lessons in acceptance from hiking the PCT
• 15:10 — Advice on grief & loss of parents at midlife
• 20:52 — Conversation on infidelity, monogamy, and honesty
• 25:58 — The six universal problems from Dear Sugar letters
• 27:44 — Why women struggle to express vulnerability
• 29:50 — The necessity of saying truths out loud / aging without shame
• 31:09 — On wild’s success and “making it”
• 35:00 — Success belonging to the lineage of women before
• 36:00 — The next life journey as an upcoming rite of passage
• 38:00 — The gratitude and privilege of aging

Tone & Style

The episode is candid, irreverent, and compassionate, weaving humor and vulnerability. Cheryl’s wisdom is hard-won and unpretentious; Reshma brings authentic curiosity and reflection, creating a relatable space for listeners navigating their own midlife transitions.

For Listeners

If you are seeking permission to embrace your own evolution, question the “best years,” or acknowledge all your mess and your triumphs with radical acceptance, this episode is for you.

Reshma’s take-home message: “Live for right now, be present, don’t wait for a deathbed moment.”

Cheryl’s personal goal: To learn and define her “crone age,” embracing the next era with courage, self-acceptance, and curiosity.

Recommended Next Steps:

• Check out Cheryl Strayed’s Dear Sugar newsletter on Substack.
• For those reflecting on loss or seeking more, read or re-read Wild or Tiny Beautiful Things.
• Embrace “saying it out loud”—whatever your secret is—it could be the start of your own rite of passage.