Wintering is a recurring life season, not a one-time crisis

May defines "wintering" broadly as any period when a person is cut off from the normal current of life — through illness, loss, professional setback, or a less nameable sense of being stuck — and argues these periods recur throughout a life rather than happening once and being permanently resolved. Just as literal winter returns every year regardless of how well someone prepared for the last one, personal wintering isn't a problem to be solved once and never faced again.

This reframing works against a common assumption that hardship is an aberration, a wrong turn from an otherwise smooth default life. May instead treats seasons of difficulty as a structural feature of being alive, something to expect and build resilience around rather than treat as evidence that something has gone uniquely wrong.

Seeing wintering as cyclical rather than exceptional changes how a person can relate to being in one: less panic about permanence, more attention to what the season is actually asking of them right now.

Takeaway: expect hard seasons to return, and build a relationship with them rather than treating each one as a unique catastrophe.