We begin by pointing to how combining traditional Buddhist training with transforming psychological and social conditioning and unresolved material suggests the contours of a contemporary path of awakening. We then identify some of the main areas of the contemporary “shadow,” of unconscious, unresolved conditioning and developmental wounds, such as anger, fear, death, shame, conflict, trauma, grief, sexuality, and so on. We then give a “map” of four stages in the transformation of the shadow (particularly in a meditative context), starting with finding ways to access the shadow, then learning to be with and explore the shadow, then transforming the shadow, and then integrating the shadow work with daily life.