Podcast Summary: How to Rest When Life Is Overwhelming (w/ Katherine May)

Podcast: How to Be a Better Human
Host: Chris Duffy (TED)
Guest: Katherine May, author of “Wintering” and “Enchantment”
Release Date: August 25, 2025

Episode Overview

This episode dives into the inevitable dark periods—what Katherine May calls “winterings”—that everyone experiences in life. Through personal stories, literary insights, and practical advice, Katherine and Chris dismantle the myths surrounding difficult seasons. They invite listeners to accept pain as a vital part of being human and discuss the power of rest, radical acceptance, and finding small moments of beauty and connection, even during hardship.

Key Discussion Points & Insights

1. Understanding “Wintering” as a Metaphor for Difficult Times

• Defining Wintering (01:08)

  • Katherine reads from her book: “Wintering is a season in the cold. It's a fallow period in life when you’re cut off from the world, feeling rejected, sidelined, blocked from progress, or cast into the role of an outsider.”
  • These periods might result from illness, loss, humiliation, or transition. Some happen suddenly; others creep in slowly.

• The Inevitability of Hardship (06:01, 06:35)

  • Chris and Katherine discuss society’s belief that hard times are avoidable and shameful, which leaves people unprepared to cope.
  • Quote (Katherine May, 06:35): “There’s a really profound belief that we fail if we winter… But then, of course, when it visits us, we are left with no toolkit to process what's happening. And, of course, guilt is inevitably the thing that comes up.”

2. Radical Acceptance of Suffering

• Letting Winter In (07:47)
  • Chris reads: “We may never choose to winter, but we can choose how.” Katherine notes it's about mindful acceptance, not rushing or denial.
  • Quote (Katherine May, 08:46): “We can allow ourselves to be mindful through that process, to notice everything that’s happening, to ask what’s going on, to try and find a way to stop resisting it. Because, as Alan Watts says, a lot of the pain that we experience is the running from the pain.”

3. Rejecting Toxic Positivity & Clichés

• Against “Silver Linings” (12:08)

  • Both share fury at platitudes like “everything happens for a reason” or “what doesn’t kill you makes you stronger.”
  • Quote (Chris Duffy, 12:11): “I could rip your jugular vein out right now.”
  • Katherine shares a current personal “winter”—her husband’s recent cancer diagnosis—calling for honest acknowledgment instead of empty reassurances (12:25).

• The Real Need: Community and Understanding

  • What people need most is simple human connection: “God, that’s awful. I’m so sorry.” (Katherine May, 12:25)
  • Suffering and decline are part of life and don’t negate its value (14:19).

4. The Value of Shared Experience

• What We Need to Hear (15:02)

  • Quote (Chris Duffy, 15:02): “The message that at least I needed to hear and that I think a lot of people need to hear… is not ‘you’re going to be better’ or ‘it’s all going to be okay.’ It is: ‘you are not alone.’”

• Vulnerability as Connection

  • Opening up about struggles lets people help and builds true community (25:35).

5. The Role of Art, Emotion, and Kindness During “Wintering”

• Heightened Sensitivity (21:47, 23:03)
  • Chris: Emotional pain strips one’s defenses, making art, beauty, and kindness intensely felt.
  • Katherine’s anecdote about a neighbor helping move tiles—a mundane act transformed into a transcendent moment by vulnerability (23:03).

6. Receiving and Accepting Help

• Practical Strategies (25:35)
  • Katherine shares tips for accepting care: being honest about how you’re really doing, letting others help with small things, and reframing receiving help as an act of generosity toward those who care.

7. The Limitations of “Hero’s Journey” Narratives

• Chaotic vs. Heroic Narratives (28:26, 30:07)

  • Most life challenges don’t offer a neat arc or triumphant ending. People struggle more with ongoing, unnamed, or unresolved difficulties.

• Richness in Transformation (32:53, 33:00)

  • Both discuss “the woods” as a metaphor—never fully escaped, but navigated with new tools and complexity.
  • Katherine quotes Shakespeare’s “Full Fathom Five,” highlighting beauty and strangeness in transformation.

8. Adapting to “What Is” Rather than Seeking Cure

• Living within Limits (34:02, 34:40)
  • Sometimes the lesson is to live the best life possible within new parameters, not to “fix” everything.

9. Moving from Winter to “Enchantment”

• Finding Wonder Again (38:06)

  • Katherine discusses her book “Enchantment,” focusing on reawakening wonder after dark times. This isn’t about big adventures but rediscovering magic in the small and everyday—earth, water, fire, air.

• Laughter as Survival (41:05, 41:17)

  • Gallows humor helps process grief—serious topics are often the most absurd and funny in private.

• Sensory Practices for Reconnection (42:56, 45:03)

  • Practical tips: Go barefoot on grass, swim in cold water, find little rituals that ground you in your body and environment.

Notable Quotes & Moments

| Timestamp | Speaker | Quote/Description | |-----------|--------------|--------------------------------------------------------------------------------| | 01:08 | Katherine May| “Everybody winters at one time or another… Wintering is a season in the cold.” | | 06:35 | Katherine May| “There’s a really profound belief that we fail if we winter.” | | 08:46 | Katherine May| “Winter is like necessary change arriving. Not welcome change, but necessary change.” | | 12:11 | Chris Duffy | “I could rip your jugular vein out right now.” (In reaction to clichés) | | 12:25 | Katherine May| “All I need right now is for people to say, God, that's awful. I’m so sorry.” | | 14:19 | Catherine May| “Many things that don’t kill you actually leave you much weaker.” | | 15:02 | Chris Duffy | “You are not alone. You're not the only person who's ever experienced this.” | | 16:07 | Chris Duffy | “Life is by its very nature uncontrollable… our suffering comes from the fight we put up against this fundamental truth.” (Reflecting on Alan Watts) | | 23:03 | Katherine May| “The tiniest thing can just feel transcendent… my neighbor just came out to help [with tiles]… it was a little bit of magic, honestly.” | | 25:35 | Katherine May| “I've been disciplining myself… just practicing that sentence: 'things are really rough today, actually.'” | | 30:07 | Katherine May| “The hero's journey doesn't often really apply to illness. It's often random, chaotic… acknowledging those narratives is so, so tough.” | | 32:53 | Chris Duffy | “I don’t think that you ever leave the woods. You just go to nicer or less nice parts of the woods, but you’re always in the woods.” | | 33:00 | Katherine May| Quotes Shakespeare’s “Full Fathom Five” to illustrate transformation. | | 34:40 | Katherine May| “How do you adapt to this life, this life that you’ve been given? That was the point at which her life suddenly got way better.” | | 41:05 | Chris Duffy | “For me, laughter and humor is the way that you release the tension…” | | 41:17 | Katherine May| “I’m such a believer in gallows humor… we need it because it's how you acclimatize yourself to the language.” | | 42:56 | Katherine May| “The simplest way you can just make contact with the actual Earth again… is just taking off your shoes.” | | 45:17 | Chris Duffy | “I jumped into this body of water… and I just went yee haw.” |

Timestamps for Key Segments

• [01:08] - Defining “Wintering”
• [06:35] - Societal shame around struggle
• [08:46] - Radical acceptance and mindful suffering
• [12:08/12:25] - Rejecting toxic positivity and clichés
• [23:03] - Kindness and beauty in small moments
• [25:35] - Receiving help and being open
• [28:26] - Unhelpful narratives (hero’s journey)
• [33:00] - The value of transformation and complexity
• [38:06] - Moving toward “enchantment”
• [42:56] - Everyday practices for reconnection
• [45:17] - Laughter, humor, and personal rituals

Tone & Final Thoughts

The conversation is candid, warm, and at times deeply moving. Chris and Katherine use humor and literary references to make difficult topics relatable, refusing easy answers in favor of honesty and connection. Listeners are left with permission to embrace their own “winterings,” rest without shame, and seek beauty and small wonders even in the darkest seasons.

This episode is essential for anyone facing overwhelm, offering both comfort and practical ideas for moving forward—while honoring exactly where you are.