While Jung hardly mentions Schelling in his writings, Schelling's philosophy anticipates many elements of his psychology. In Schelling's Philosophical Investigations into the Essence of Human Freedom philosophy reaches a crisis point, which prepares the way for Schelling's positive philosophy as well as existentialism and the later ascendancy of depth psychology as Jung conceived it. A closer examination of the nature of this crisis as it finds expression in Schelling's Investigations, which takes clues from Berdyaev's and Kierkegaard's existential philosophy, provides a revealing perspective on the present post-modern condition of our culture. This essay is an attempt to examine Schelling's text with regard to the role the imagination plays in it in order to gain deeper insight into the cultural relevance of Jung's psychology. While Jung hardly mentions Schelling in his writings, Schelling's philosophy anticipates many elements of his psychology. In Schelling's Philosophical Investigations into the Essence of Human Freedom philosophy reaches a crisis point, which prepares the way for Schelling's positive philosophy as well as existentialism and the later ascendancy of depth psychology as Jung conceived it. A closer examination of the nature of this crisis as it finds expression in Schelling's Investigations, which takes clues from Berdyaev's and Kierkegaard's existential philosophy, provides a revealing perspective on the present post-modern condition of our culture. This essay is an attempt to examine Schelling's text with regard to the role the imagination plays in it in order to gain deeper insight into the cultural relevance of Jung's psychology.