In this essay I study the approaches to psychology of C. G. Jung and James Hillman. Even though Hillman’s approach stems from the work of Jung, there are considerable differences in their psychologies that need to be discerned and accounted for, both in approaches and goals. In order to discern the two different approaches, I discuss the following subjects that serve to delineate differences in their psychologies: unity vs. multiplicity of centres, hierarchy of the psyche vs. depths, the anima/animus syzygy, wholeness and psychological differentiation, the archetype-in-itself and the archetypal image, the anima mundi [soul of the world], therapy and the rainmaker myth, the symbol and the archetypal image, the aesthetic and the ethical attitudes, the psychology of the three and the psychology of the four, and individual and community. I apply the teachings of Indian wisdom, especially through the writings of the contemporary master, Sri Aurobindo, in order to support Jung. Jung’s synthesis, I argue, leads to the spiritualization of nature and the subjection of the ego-will to a higher will as well as an in-depth transformation of the feminine principle. It leads towards the future in a way that Hillman’s psychology does not.