
Wintering
The Power of Rest and Retreat in Difficult Times
Categories
Nonfiction, Self Help, Psychology, Health, Memoir, Nature, Mental Health, Audiobook, Essays, Book Club
Content Type
Book
Binding
Hardcover
Year
2020
Publisher
Riverhead Books
Language
English
File Download
PDF | EPUB
Wintering Plot Summary
Introduction
I remember the first time I truly understood winter. It wasn't the meteorological season, but the deep, personal winter that swept through my life unexpectedly. My career was thriving, my relationships seemed solid, and then suddenly—darkness fell. A health crisis combined with financial strain and the ending of a significant relationship created a perfect storm. I found myself unable to function as I normally did, retreating from social connections, feeling a profound sense of vulnerability and loss. For months, I fought against this state, seeing it as weakness, as failure. I pushed harder, tried to maintain appearances, and exhausted myself completely in the process. What I didn't realize then—what many of us fail to see—is that these dormant periods in our lives aren't anomalies to be avoided or powered through. They are inevitable, necessary phases in the cycle of our existence. Just as nature embraces the rhythm of seasons, human lives follow patterns of growth, abundance, shedding, and rest. These personal winters—periods of loss, illness, grief, disappointment, or transition—offer unique gifts if we learn to navigate them with intention rather than resistance. They invite us to turn inward, to reassess, to build resilience, and to prepare for renewal. This wisdom isn't about glorifying suffering but about recognizing the transformative potential of our most challenging seasons and finding strength in the process of weathering them with grace.
Chapter 1: The Invitation of Winter: Recognizing Life's Inevitable Fallow Periods
The call came on an ordinary Tuesday afternoon. I was mid-meeting when my phone lit up with my sister's name. Something in me knew before I even answered—our father had passed away after his brief but intense battle with cancer. The world tilted on its axis. Within hours, I was on a plane, flying across the country, suspended between the life I had been living that morning and whatever lay ahead. By nightfall, I was sitting in my father's study, surrounded by his books, his notes, the half-finished cup of tea he would never return to finish. For many of us, winters arrive this way—with a phone call, a diagnosis, a pink slip, or a conversation that ends a relationship. They arrive uninvited and unwelcome, thrusting us into a season we didn't choose. My father's death ushered in the coldest winter of my life. In the months that followed, I moved through days in a fog, going through motions while feeling fundamentally changed. Tasks that once seemed simple became monumental. Joy felt distant and inaccessible. The world continued around me, but I was operating at a different pace, in a different season entirely. What surprised me most was how isolating this experience felt. Friends offered initial comfort but soon expected me to "move on" or "get back to normal." Colleagues grew impatient with my diminished capacity. In our always-productive, perpetually-sunny culture, winter is seen as a state to overcome rather than a season to honor. We lack rituals for these fallow periods, these times when we are called to retreat and process rather than produce and perform. Yet winter arrives for everyone eventually. Loss, illness, failure, burnout, depression, creative blocks, major transitions—all these experiences force us into a dormant period. They slow us down, strip away pretenses, and confront us with our vulnerability. The invitation of winter isn't to fight harder but to surrender to a different rhythm, to acknowledge that we cannot always be in bloom. The wisdom of winter lies in recognizing these periods as natural, inevitable parts of human experience rather than aberrations or personal failings. When we resist winter—when we deny ourselves the time to process grief, heal from trauma, recover from burnout, or simply be unproductive for a season—we only prolong its stay. Learning to name our winters, to spot their approach on the horizon, is the first step toward developing the capacity to weather them with intention and grace.
Chapter 2: The Bodily Experience: How Winter Manifests Physically
Maria had always prided herself on her resilience. As a single mother running her own business, she had navigated countless challenges with determination and grit. The warning signs began subtly—persistent headaches, disturbed sleep, a constant knot in her stomach. She dismissed these signals, pushing through with her usual tenacity. Then came the day when her body made the decision her mind wouldn't: she collapsed during a client presentation. Later, in the hospital, a doctor gently explained that her body had essentially gone on strike after months of chronic stress and neglect. "Your body has been sending you messages for months," he told her. "When we ignore those whispers, they eventually become shouts." The diagnosis was burnout complicated by severe adrenal fatigue. Her prescription wasn't medication but a radical period of rest and recovery. For someone who measured her worth through productivity, this felt like a prison sentence. How could she possibly stop when so many people depended on her? The physical manifestations of our personal winters are as varied as they are revealing. Some bodies respond with exhaustion so profound that simple tasks become monumental. Others manifest pain—headaches, backaches, digestive issues—physical expressions of emotional burdens we're carrying. Sleep disturbances are common, either insomnia that keeps us wired and anxious or hypersomnia that has us seeking escape through extended slumber. Our immune systems may falter, leaving us vulnerable to every passing virus. Our appetites fluctuate—some find themselves unable to eat while others seek comfort in food. For some, the body's winter arrives with a heaviness that makes movement feel impossible. The simplest actions—showering, preparing a meal, walking to the mailbox—require tremendous effort. Others find themselves restless, unable to settle, driven by an anxious energy that never resolves into meaningful action. Some experience a sensory dulling—colors seem less vivid, food tastes bland, touch brings little comfort. Others become hypersensitive, overwhelmed by stimuli that normally wouldn't register. What's remarkable is how precisely our bodies communicate what our conscious minds often deny. Long before we're willing to acknowledge that we're grieving, burning out, or sliding into depression, our bodies begin sending signals. These physical manifestations aren't weaknesses or inconveniences—they're sophisticated communication systems alerting us to imbalances that require attention. Learning to interpret and honor these bodily signals is crucial winter wisdom. Our culture often encourages us to override physical limitations, to push through fatigue, to medicate symptoms without addressing causes. But in doing so, we miss the opportunity to listen to the profound intelligence of our bodies. When we treat these physical manifestations with respect rather than resistance, they become compass points guiding us toward the kind of care we most need during our dormant seasons.
Chapter 3: Rituals and Rhythms: Finding Meaning in Winter's Darkness
When David lost his wife to cancer after thirty-seven years of marriage, he found himself disoriented in every sense. The rhythms that had structured their shared life—morning coffee on the porch, weekend gardening, evening walks—suddenly dissolved, leaving days that stretched before him like an unmarked landscape. Well-meaning friends urged him to "stay busy" and "find distractions," but these suggestions felt hollow. Instead, David found himself drawn to the creation of new rituals that acknowledged rather than avoided his grief. Each morning, he began lighting a candle at breakfast, a simple act that honored his wife's presence in his continuing life. On Sundays, he visited the botanical garden they had loved, sitting on the same bench where they had often rested. He established a habit of writing letters to her—not to send, of course, but to maintain their conversation across the divide. These weren't grand gestures, but small anchors that gave shape to his days and meaning to his experience of loss. Humans are ritual-making creatures. Throughout history and across cultures, we have created ceremonies and practices to help us navigate life's transitions and challenges. Traditional societies recognized winter—both literal and metaphorical—as a time requiring specific observances. They understood that darkness calls for light, that barrenness needs the promise of return, that communities must hold space for those experiencing loss or hardship. In our secular, individualistic era, many of these collective rituals have disappeared, leaving us to navigate our personal winters without maps or guides. This absence is felt most acutely during periods of grief, when our internal experience diverges so dramatically from the external world continuing unchanged around us. Without rituals to mark this divergence, we often feel increasingly isolated, unseen in our suffering. Creating personal rituals during life's winter seasons serves multiple purposes. They provide structure when normal routines have been disrupted. They offer symbolic expression for feelings that may exceed our capacity for verbal articulation. They connect us to deeper meanings beyond our immediate circumstances. Even simple practices—lighting candles, taking contemplative walks, creating small altars with meaningful objects, establishing regular times for reflection or remembrance—can become powerful touchstones. Equally important is finding sustainable rhythms during these challenging periods. Winter calls for a different pace—slower, more deliberate, with greater attention to fundamentals. This might mean establishing gentler morning routines, creating clear boundaries around energy expenditure, prioritizing rest, or simplifying commitments. These rhythms should honor our diminished capacity without surrendering to complete inertia. The wisdom lies in recognizing that meaning isn't found despite the darkness but often through it. When we create intentional practices that acknowledge our experience rather than deny it, we discover that even the bleakest seasons can be navigated with dignity and depth. These rituals don't eliminate pain, but they transform it from something to merely endure into something that can be integrated into the continuing story of our lives.
Chapter 4: Retreat and Regeneration: The Hidden Power of Stepping Back
James had been the consummate achiever—valedictorian, scholarship recipient, youngest partner at his law firm. His identity was so thoroughly entwined with accomplishment that when a case went catastrophically wrong, costing the firm a major client, he experienced it as more than a professional setback. It was an existential crisis. The shame was overwhelming. Unable to face his colleagues, he requested a leave of absence, retreating to a small cabin owned by his family in the mountains. The first weeks were excruciating. Without the constant validation of work, without the familiar scaffolding of deadlines and expectations, he felt utterly lost. He slept fitfully, his mind racing with recriminations and worst-case scenarios. He considered resigning altogether, convinced his career was irreparably damaged. But gradually, almost imperceptibly, something began to shift. The rhythms of the natural world around him—the sunrise, the movements of animals, the weather patterns—began to reset his internal clock. Without intending to, James found himself living more simply. He cooked basic meals, took long walks, read books that had nothing to do with law. He began journaling, first about the case and his perceived failures, but eventually about deeper questions: What would success look like if it weren't defined by professional achievement? What parts of himself had he neglected in his single-minded pursuit of career advancement? What values truly mattered to him beyond status and recognition? Our culture celebrates constant engagement, perpetual productivity, and uninterrupted visibility. In this context, retreat is often misinterpreted as escapism or abdication. We worry that stepping back means giving up, that removing ourselves from familiar environments signals defeat. Yet throughout history, periods of retreat have been recognized as essential components of growth and transformation. Religious traditions incorporate retreats as fundamental practices. Creative luminaries often withdraw to fallow periods between bursts of productivity. Indigenous cultures include vision quests and similar practices of separation as crucial rites of passage. What these traditions understand is that certain kinds of development can occur only when we step away from ordinary patterns and pressures. Retreat creates space for reflection that's impossible amid the constant stimulation of everyday life. It allows for the emergence of insights that can't break through the noise of regular routines. It permits emotions to surface that might otherwise remain buried beneath layers of busyness and distraction. True retreat differs from mere escape. It's not about avoidance but about creating conditions for regeneration. It may involve physical removal—to nature, to quieter environments, to simplified circumstances—but it always involves an interior journey as well. This dual movement, away from external demands and toward internal truths, creates the conditions for profound renewal. For James, three months of retreat accomplished what no amount of conventional problem-solving could have achieved. He returned to his firm not with a strategic plan to repair his professional reputation, but with a fundamentally different relationship to his work and identity. The winter of his retreat had allowed essential parts of himself—curiosity, creativity, capacity for joy—to regenerate after years of neglect. In stepping back, he had actually moved forward in the most meaningful sense.
Chapter 5: Learning from Nature: How the World Weathers Winter
On a bitter January morning, Emma stood at the edge of an oak forest, participating in a research project documenting winter survival strategies. As a biologist, she understood intellectually what was happening beneath the apparently lifeless landscape, but today she was experiencing it with new eyes. The previous month, she had received a diagnosis that upended her life—a chronic condition that would require significant adaptations. Now, notebook in hand, she surveyed the winter forest with both scientific precision and personal resonance. The oaks had dropped their leaves months ago, a strategic surrender rather than a defeat. By shedding these appendages that would demand energy and expose surface area to damaging winter winds, the trees conserved resources for essential core functions. Underground, their root systems remained active, though at a much slower metabolic rate. They weren't "fighting" winter; they were elegantly adapted to it. Nearby, Emma documented signs of animals employing diverse winter strategies. Some had migrated, following ancient pathways to more hospitable climates. Others had entered hibernation, dramatically lowering their body temperatures and metabolic rates to conserve energy. Still others had developed specialized adaptations—thicker coats, food storage systems, communal living arrangements—that allowed them to remain active despite harsh conditions. Nature offers profound wisdom about navigating difficult seasons. Unlike humans, who often resist changes in circumstances or capacity, natural systems demonstrate remarkable flexibility. They don't waste energy fighting inevitable cycles. Instead, they have evolved sophisticated responses that honor the reality of seasonality while ensuring continuation of life's essential functions. Consider the intelligence of deciduous trees. Rather than attempting to maintain summer growth patterns during winter's resource scarcity, they strategically redirect energy toward root development. They don't experience leaf loss as failure but as adaptation. When spring returns, they're positioned for robust renewal precisely because they honored winter's limitations. Or consider hibernating animals. Bears don't resist the onset of winter with anxious activity. They prepare—building fat reserves, creating sheltered dens—and then surrender to a period of profound rest. Their bodies undergo remarkable physiological changes, essentially upgrading their systems during this dormant time. They emerge from hibernation not despite their winter retreat but because of it. Even in the harshest environments, life demonstrates astonishing creativity in response to limitation. Desert plants develop water storage systems. Arctic creatures evolve insulation strategies. Migratory species navigate thousands of miles guided by innate wisdom about when to move and when to stay. For Emma, these observations became more than scientific data—they became a framework for approaching her own changing circumstances. Perhaps her diagnosis wasn't just a limitation to fight against but a reality calling for creative adaptation. Perhaps certain activities needed to be temporarily surrendered to conserve energy for core priorities. Perhaps her slower pace wasn't failure but an appropriate response to changed conditions. Nature reveals that wisdom lies not in resistance to difficult seasons but in developing appropriate responses to them. It demonstrates that limitation often catalyzes innovation, that rest precedes renewal, that adaptation is not capitulation but intelligence. Most importantly, it shows that winter—while challenging—is never the end of the story. Life continues, often beneath the surface, preparing for expressions that will emerge when conditions shift once again.
Chapter 6: Community in Cold Times: Finding Connection Through Shared Struggle
The cancer support group met every Tuesday evening in the hospital's community room. Sarah had resisted attending for months after her diagnosis, convinced she could handle everything independently. "I'm not a joiner," she told her doctor when he suggested it. "And I don't want to sit around with a bunch of people feeling sorry for themselves." But as treatment progressed and isolation deepened, she reluctantly agreed to try one session. What she found defied her expectations. The group wasn't characterized by self-pity but by remarkable honesty and even unexpected humor. People spoke openly about fears she had been afraid to name even to herself. They shared practical solutions to challenges she was facing—how to manage side effects, navigate medical bureaucracy, talk to children about illness. Most surprisingly, they celebrated each other's small victories with genuine joy. During her third session, an older man named Marcus shared that his recent scan showed progression rather than improvement. The group held space for his grief without platitudes or false reassurances. Later, as they were leaving, he stopped Sarah in the hallway. "I noticed you're still trying to carry this alone," he said gently. "We all did that at first. But winter is too cold to face without companions." Humans evolved as intensely social creatures, dependent on community for survival. Yet in personal winters—times of illness, grief, failure, or hardship—we often withdraw from connection precisely when we most need it. Sometimes this withdrawal stems from shame, the belief that our struggles reflect some personal inadequacy. Sometimes it comes from fear of burdening others or appearing vulnerable. Sometimes it arises from the painful reality that many relationships prove inadequate in the face of serious difficulty. Traditional societies understood the essential role of community during life's challenging seasons. They had established rituals for supporting members through illness, grief, and hardship. They recognized that struggles weren't individual problems but community concerns requiring collective response. Modern life has eroded many of these structures, leaving us to navigate difficulties with inadequate support systems. What Sarah discovered in her support group was an ancient form of community—people united not by social similarity or mutual interests but by shared experience of a difficult reality. These "communities of struggle" exist in many forms: grief groups, addiction recovery circles, support networks for parents of children with special needs, gatherings of those navigating divorce or job loss. What distinguishes these communities is their capacity to hold space for authentic experience without premature reassurance or problem-solving. True winter communities offer several irreplaceable gifts. They normalize experiences that can feel isolating and shameful when faced alone. They provide practical wisdom from those who have navigated similar terrain. They offer mirroring—the profound experience of being truly seen and understood. Perhaps most importantly, they demonstrate that community isn't built only through shared joys and successes but through mutual vulnerability in difficult seasons. For Sarah, the support group gradually became a lifeline. Not because it changed her prognosis or eliminated her fears, but because it provided companionship through territory that was never meant to be traversed alone. The wisdom she gained wasn't just about cancer but about the fundamental human need for connection through all seasons—especially the coldest ones. Authentic community during winter periods doesn't deny darkness but brings light to it through shared recognition and companionship. It reminds us that while certain journeys must be walked personally, they need never be walked in complete isolation. In finding others who understand our particular winter, we discover not only practical support but the profound reassurance that we remain connected to humanity even in our most challenging seasons.
Chapter 7: The Thaw: Emerging from Winter with New Wisdom
The invitation to return to work came eighteen months after Robert's breakdown. His former employer had heard through mutual connections that he was doing better and offered a position similar to the one he had left during his crisis. It was a generous gesture that would have resolved many practical problems—his depleted savings, the gap in his resume, the awkward explanations about his absence. Yet as he considered it, he felt an unexpected resistance. It wasn't anxiety about whether he could handle the workload. It was something deeper—a recognition that returning would mean erasing the transformative period he had just navigated. During his breakdown and slow recovery, Robert had discovered parts of himself long buried beneath professional accomplishment and social expectations. He had reconnected with his love of woodworking, spending hours in patient creation rather than constant productivity. He had developed a meditation practice that grounded him in ways his former achievement-oriented life never had. He had cultivated deeper relationships with fewer people, prioritizing authenticity over networking. Most importantly, he had developed a compassionate relationship with his own vulnerability, no longer seeing his limitations as weaknesses to overcome but as essential aspects of his humanity. The job offer forced a reckoning: Was this winter simply a disruption to be minimized, a detour from his "real life"? Or had it been a necessary passage into a more integrated way of being? After much reflection, he declined the position, choosing instead to build a life that incorporated what winter had taught him—one that included meaningful work but wasn't defined exclusively by professional identity or external validation. Emerging from life's winter seasons is rarely a simple return to previous conditions. Like the natural world after winter, we don't merely revert to our former state but emerge transformed, often in subtle but significant ways. The thaw is not about erasing winter's effects but about integrating its lessons into our continuing journey. This integration process requires discernment. When the acute phase of difficulty begins to subside—when grief softens its grip, when health improves, when crisis resolves—we face important choices about what to carry forward and what to leave behind. Some winter adaptations were merely survival strategies appropriate for extreme conditions but not for ongoing life. Others represent profound wisdom that would impoverish us to abandon. The thaw also requires patience. Nature doesn't rush from winter to summer but moves through spring, a transitional season with its own rhythms and requirements. Similarly, human emergence from difficult periods needs time and space. Premature pressure to "get back to normal" often derails the integration process, leaving valuable insights unincorporated and setting the stage for future difficulties. Perhaps most importantly, the thaw invites us to honor winter's gifts even as we welcome renewed warmth and light. These gifts vary widely: increased compassion born from suffering, clearer priorities emerging from limitation, deeper authenticity forged in crisis, enhanced resilience developed through endurance. Some discover creativity that emerged only when conventional paths were blocked. Others find spiritual depth accessed through confrontation with mortality or meaning. Many develop heightened appreciation for simple joys previously overlooked. For Robert, honoring winter's wisdom meant building a life fundamentally different from his pre-breakdown existence—one that incorporated regular periods of retreat, that balanced productive work with creative expression, that prioritized depth over breadth in relationships. The breakdown that had once seemed like the worst thing that could happen gradually revealed itself as a painful but necessary disruption of patterns that were never truly sustainable. This is perhaps winter's greatest paradox: What appears initially as devastating loss or limitation often creates space for emergence of gifts that wouldn't otherwise have developed. Not because suffering is inherently redemptive, but because navigating difficult seasons requires us to access deeper resources and wisdom than prosperity typically demands. When we emerge carrying these resources rather than simply seeking to recover what was lost, we honor winter's difficult but essential role in the continuing story of our lives.
Summary
Throughout life's inevitable winters—those periods of loss, illness, failure, transition, or grief—we often resist the very conditions that could lead to our deepest growth. We fight against the slowing down, the limitations, the vulnerability these seasons demand. Yet as we've seen through diverse experiences, winter is not merely something to survive but a vital phase in the cycle of human development. The wisdom of winter lies not in escaping it but in learning to move with it intentionally, allowing its particular gifts to emerge. The practices that sustain us through these dormant periods are both ancient and accessible. They begin with recognition—naming our winters rather than denying them, acknowledging their legitimacy in our lives. They continue with surrender—not as resignation but as acceptance of a different rhythm for this season. They involve creating meaningful rituals that honor our experience rather than minimize it. They require finding companions who can witness our struggles without rushing to fix them. Most importantly, they call us to trust that renewal will come, not despite the winter but because of it. When we embrace these practices, we discover that our capacity to weather difficult seasons becomes one of our most valuable assets, a source of resilience that serves not only ourselves but all those we encounter. Winter is not the end of the story but an essential chapter in our becoming more fully human.
Best Quote
“We have seasons when we flourish and seasons when the leaves fall from us, revealing our bare bones. Given time, they grow again.” ― Katherine May, Wintering: The Power of Rest and Retreat in Difficult Times
Review Summary
Strengths: The reviewer appreciates the concept of "wintering" and the nearly poetic writing style of the author. They also enjoy the author's voice throughout the book. Weaknesses: The book is perceived as being written from a point of extreme privilege, with scenarios that may not be relatable to the majority of people facing hardships. It also resembles a "find yourself" self-help book. The reviewer feels the author did not fully explore certain topics and would have preferred a longer book for more in-depth discussion. Overall Sentiment: Mixed Key Takeaway: While the book is beautifully written and offers valuable insights into living life according to personal values, it is criticized for its privileged perspective and lack of depth in exploring significant issues.
Trending Books
Download PDF & EPUB
To save this Black List summary for later, download the free PDF and EPUB. You can print it out, or read offline at your convenience.

Wintering
By Katherine May










