This chapter sets out to explore how spirituality and transcendence in old age can be understood. It follows the clues of ancient wisdom in order to show the modern significance of its concepts for spirituality of old age in a comparison with Lars Tornstam's theory of gerotranscendence. The worldview of gerotranscendence articulates a countercultural blueprint for a way of life that can be linked to the monastic ideal in the tradition of Christian piety.