This article analyses and evaluates the need and nature of discernment in contemporary spirituality. It first describes the complexity of spirituality as a phenomenon that has, on a cultural, anthropological and mystical level, lost its boundaries and expanded beyond all existing horizons. It motivates how, like a ship sailing on the high seas, needs a compass, discernment is needed in the face of this complexity. The article then focuses on two paradigms for reflection on discernment. First, it examines discernment as it is practised in the house of study in the Jewish tradition, and describes how this practice reveals two seminal dimensions of discernment. It then analyses and evaluates discernment in the community of desert monks in the Christian tradition which illustrates the significance of discernment for spirituality. It describes the conversation within a spiritual community as an essential element of discernment as the highest form of spiritual practices. Discernment as seeing and appreciating differences of opinion is a sign of God’s way. The article concludes that discernment permeates all spiritual practices and represents the exercise of all exercises without which one is without a compass on the high sea of spirituality.