Wintering as a Strategic Capability: Why Rest Matters

Katherine May describes wintering--the difficult, inevitable seasons of life--not as a personal failure or a flaw in one's progress, but as a biological and psychological necessity. Our modern obsession with constant, linear growth creates a distorted view of reality that prevents effective action. By examining the consequences of toxic positivity and performative rest, May shows that the most resilient people are those who retreat to conserve energy. This perspective offers an advantage to those who can distinguish between control and agency, allowing them to stop fighting unchangeable circumstances and focus their energy on the work that sustains communities during crises.

The Trap of the Upward Escalator

We are conditioned to see life as an uninterrupted upward graph. When that line dips due to grief, illness, or burnout, we treat it as a malfunction. May argues that this denial drives our exhaustion. By refusing to accept the reality of a down season, we waste emotional resources trying to force a return to normal.

> I think underlying that conclusion that many of us reach about it being a personal failing is this fallacy that life will be an escalator of uninterrupted progress but that is just not how it goes.
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> -- Katherine May

The result of this fallacy is a loop of performative behavior. When we feel pressured to maintain a perfect image, we reject the reality of our own suffering. This creates a blind spot: we become unable to listen to others, preferring to offer slogans instead of meeting them in their difficulty. Over time, this erodes the social fabric, such as community and face-to-face connection, that we need to survive the next inevitable winter.

Danger Signaling and the Digital Panopticon

May traces our modern state of perpetual anxiety to what she calls danger signaling. Borrowing from evolutionary biology, she describes how social media functions like rabbits fleeing a threat: one signal triggers a cascade of panic, even when the original source of danger is long gone.

> We have learned that one of the effective strategies for gaining followers and interest with our storytelling online is to send out danger signals... we are passing on these chains of fear and danger and then we are exhausted and we are so exhausted that we cannot face social life anymore.
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> -- Katherine May

The hidden consequence is a depletion of our agency. When we constantly process danger signals, we lose the ability to distinguish between what we can control and what we can only influence. This leads to a state of paralysis where we feel responsible for everything but capable of acting on nothing. The advantage lies in breaking the chain by limiting news intake and focusing on our immediate, tangible environment.

The Hidden Work of Agency

A key insight in the conversation is the distinction between empathy and compassion. Empathy is the raw, often overwhelming feeling of powerlessness when witnessing global crises. Compassion is empathy plus agency. May suggests that the people who hold the world together are not those shouting the loudest, but those performing the hidden work, such as caregivers, teachers, and neighbors who operate outside the spotlight.

This requires a shift in how we view rest. Most people view rest as a luxury or a selfish act that must be deferred until a crisis ends. May flips this: rest is the maintenance required to keep the system running. Without it, the hidden work stops, and the system collapses under the weight of burnout.

Key Action Items

• Audit Your Information Diet (Immediate): Reduce news consumption to once per day. Treat information as a finite resource rather than background noise that must be monitored to stay informed.
• Reclaim the Watch (Over the next quarter): If you wake in the middle of the night, stop viewing it as a problem. Do not check devices. Use this time for reading or quiet reflection, treating it as a natural, restorative phase of sleep rather than a medical failure.
• Establish Low-Friction Rituals (12-18 months): Stop waiting for permission to mark transitions. Create simple, repeatable rituals, such as watching the sunrise or seasonal gatherings, that acknowledge changes in your life or the environment, regardless of whether they have social validation.
• Shift from Control to Agency (Ongoing): When facing a crisis, map your sphere of influence. If you cannot control the outcome, identify one small, concrete action within your reach. This compassion in action is the only way to process feelings of helplessness.
• Reject Performative Wellness (Ongoing): If a habit, such as cold-water swimming, becomes about biohacking or social media validation, stop. Return to the practice only if it provides genuine, intrinsic pleasure. If it feels like work, it is not rest.