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[Embracing the Seasons of Life: A Conversation on Wintering and Enchantment]-[How to rest when life is overwhelming (w/ Katherine May)]

How to Be a Better Human · B2 · 2025-08-25

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📋 Summary

Embracing the Seasons of Life: A Conversation on Wintering and Enchantment

In this episode of How to Be a Better Human, host Chris Duffy sits down with acclaimed author Katherine May to discuss her poignant works, Wintering: The Power of Rest and Retreat in Difficult Times and Enchantment: Awakening Wonder in an Anxious Age. Together, they explore the inevitability of life's "metaphorical winters" and the transformative power of radical acceptance.

Understanding the Metaphorical Winter

Katherine May defines "wintering" as a season in the cold—a "fallow period in life" where one may feel sidelined, rejected, or blocked from progress. Whether triggered by illness, bereavement, professional failure, or the slow erosion of a relationship, these periods are often "involuntary, lonely, and deeply painful."

May highlights a critical societal flaw: the belief that difficult times are avoidable or a result of personal failure. She argues that we are a "guilt-laden species" that tries to ignore or dispose of these dark seasons. However, May asserts that wintering is an "inevitable" human experience. By attempting to avoid the "full bite" of these seasons, we only exacerbate our suffering. Instead, she suggests we must "invite the winter in" and practice "radical acceptance" of the necessary changes life brings.

The Problem with Toxic Positivity

Both Duffy and May share personal experiences with the limitations of well-intentioned advice. During times of crisis, platitudes like "every cloud has a silver lining" or "what doesn't kill you makes you stronger" can be deeply invalidating. May notes that these clichés often serve to protect the speaker from the reality of human fragility.

She emphasizes that we need to develop "safe spaces" to acknowledge the horror or fear of a situation without being forced into toxic optimism. As May points out, "sometimes when we're wintering, we're processing a decline or a loss," and life may not necessarily return to how it was before. The goal is not to find a quick fix, but to recognize that even within difficulty, one can live a "full and rich human existence."

Finding Connection and Care

One of the most profound insights from the conversation is the importance of letting others in. May admits that receiving care is often viewed as a "humiliation or a weakness," yet she encourages people to be honest about their struggles. By practicing the phrase, "Things are really rough today," we create a pathway for others to offer genuine, practical support.

This vulnerability allows for moments of "vital kindness," which May describes as a form of "magic." She emphasizes that we must stop trying to "finalize our comfort and security" and instead embrace the unpredictable nature of life.

The Role of Art and Enchantment

When discussing her book Enchantment, May explains that it serves as a guide for what comes after the wintering. It is about how to "re-establish contact with the world" and find wonder in the small, local, and personal aspects of life.

Both Duffy and May agree that humor—specifically "gallows humor"—is an essential tool for processing trauma. Making jokes about grim circumstances allows us to "voice the otherwise unvoiceable." Whether it is through the sensory experience of walking barefoot on the earth or finding connection through shared laughter, May encourages listeners to rely on the "feedback of their own senses" rather than seeking external validation or gurus.

Conclusion: Navigating the Woods

Reflecting on the nature of recovery, May cites the idea that we never truly "leave the woods"; we simply move to different parts of them. The journey is not about reaching a destination of simple triumph, but about experiencing a "sea change into something rich and strange." By accepting our pain as a fundamental part of the human experience, we can move forward with wisdom, finding beauty and connection even in the coldest of seasons.

🎯Key Sentences

1
Everybody winters at one time or another.
2
Please stick around to hear more after this quick break.
3
What's in your wallet?
4
Raise your hand if you want your nails to look perfect all the time.
5
That's how I've described your book when I am recommending it to friends.
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📝Key Phrases

1
state of mind
2
at one time or another
3
creep upon us
4
ratcheting up
5
falling apart
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📖 Transcript

You're listening to How to Be a Better Human.
I am your host, Chris Duffy. All of us experience winter.
Now, you might be saying, Chris, don't you live in Los Angeles, a part of Southern California that famously does not really experience winter?
And to that, I would say you are technically correct if we're talking about purely a meteorological winter.
I haven't pulled out a winter coat or seen snow falling on my house since I moved here that's true.
Often in January in L.A., I see someone wearing a heavy sweater on the street.

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