Inspired by the moving into the darkness of the Winter Solstice, we explore four understandings of darkness that can guide our practice at this time: (1) the importance of stopping, as seems to be the case at this time of year with the earth, disengaging for a period, and listening deeply; (2) being more skillful with what is difficult or challenging; (3) learning to be with what is unknown or unresolved; and (4) seeing how the darkness can, as is so with the earth, be generative and fertile. We apply these understandings mostly to our individual practice, but also to the difficulties and unknowns of our collective situation.