My conversion into a knower has been a long and winding road. From childhood reverie to the years of formal schooling, education has never ceased to lure me into its magical power. How do we really get to know/see/learn whatever happens on our educational journey? In this paper, I will re-trace my quest for knowledge that reaches beyond the boundaries of traditional epistemology. My wonderings will take me to explore, via Jung, the possibilities of imaginative education through Gnosis and Sophia. The paper intends to weave together several Jungian discourses with their versions by other thinkers who have contributed to the fields of depth psychology, esotericism, and educational philosophy.