Wintering: The Power of Rest and Retreat in Difficult Times

Content Warning: This section of the guide contains discussion of ableism.

Gather initial thoughts and broad opinions about the book.

1. May describes “wintering” as both a literal season and metaphorical periods of difficulty, isolation, and dormancy in our lives. How did this dual perspective change your understanding of challenging times? 

2. The memoir moves through the months from September to March, tracing May’s personal wintering alongside the changing seasons. In what ways does this approach remind you of other nature-focused works, like Henry David Thoreau’s Walden, which also follows seasonal cycles to explore the human experience?

3. Many memoirs about difficult periods frame them as obstacles to be conquered, yet May suggests we should “invite the winter in” (12). How does this approach compare to memoirs like Elizabeth Gilbert’s Eat, Pray, Love, which addresses personal renewal through seeking rather than retreat?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. May draws wisdom from her experience with autism, describing how she “spent a childhood permanently out in the cold” (9). When have you felt like an outsider, and how did this experience shape your approach to periods of isolation?

2. The author describes how winter swimming became a ritual that helped her endure difficult times: “By doing a resilient thing, we felt more resilient” (217). What physical practices have helped you navigate your own “winters”? How have they transformed your relationship with difficulty?

3. Throughout the book, May questions society’s insistence on perpetual productivity and positivity. When have you felt pressured to maintain cheerfulness during a personal wintering? How did you respond to these expectations?

4. May learns that her son is struggling at school and makes the significant decision to homeschool him. What radical life changes have you made in response to challenging circumstances? What insights did you gain from taking this leap?

5. The author speaks about how she lost her voice both literally and metaphorically after becoming a mother. When have you lost an essential part of your identity due to life changes? What helped you reclaim it?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. May writes that contemporary Western society has lost its connection to seasonal rhythms and rituals. How does disconnection from nature’s cycles affect one’s ability to navigate personal “winters”? What seasonal practices do you think might help restore this connection?

2. The author contrasts her experience of wintering in the UK with how Nordic cultures embrace and prepare for winter. What cultural attitudes toward difficulty, rest, or withdrawal have you observed in your own community? How do these attitudes help or hinder people during hard times?

3. May notes that today’s commercialized Halloween has lost its original function as a festival acknowledging death and liminal states. Which cultural practices do you think have been similarly divorced from their original purpose of helping people cope with darkness or loss? How might people reclaim these practices?

Dive into the book’s structure, characters, themes, and symbolism.

1. Throughout the memoir, May uses natural metaphors—hibernating dormice, wintering bees, singing robins—to illuminate human experiences. Which of these metaphors resonated most strongly with you, and why? How did it enhance your understanding of wintering?

2. May incorporates references to various literary works throughout her narrative, from Philip Pullman’s The Golden Compass to Sylvia Plath’s poem “Wintering.” How do these literary allusions enhance her exploration of winter as both physical reality and metaphor?

3. How does May’s writing style—her use of sensory details, reflective passages, and personal anecdotes—contribute to the book’s overall message about embracing winter? Which passages or techniques did you find most effective?

4. The memoir contains multiple examples of liminal spaces and states—the “watching hour” between sleep sessions, the transition between seasons, standing at Stonehenge during the solstice. What do these thresholds reveal about May’s understanding of wintering? How do they function in the narrative?

5. How does the motif of voice develop throughout the book, from May’s physical voice issues to finding authentic self-expression? What does this progression suggest about the relationship between wintering and authenticity?

6. May structures her memoir according to calendar months while arguing against a linear view of life. How does this create a productive tension in the book? What does it suggest about finding meaning in time-bound human experiences?

Encourage imaginative and creative connections to the book.

1. The book contains several examples of seasonal rituals from different cultures. What personal ritual would you design to mark your entrance into or emergence from a wintering period? What elements would make it meaningful?

2. May describes her fascination with Nordic winters and cold landscapes. Which environment would serve as your ideal retreat during a personal wintering? What specific resources would it provide for your renewal?

3. The author observes that winter is traditionally a time for certain kinds of creative work—crafts, repairs, and “slow, spiritual reading” (238). Write a list of creative activities that bring you comfort during fallow periods. How do these activities differ from your creative expression during more productive times?

Need more inspiration for your next meeting? Browse all of our Book Club Resources