This chapter weaves together insight from the twin disciplines of Positive Psychology and Integral Psychology of Sri Aurobindo and The Mother with the aim of exploring possibilities of the amalgamation of the psychological and spiritual domains of experience. It explores the interweaving themes of the nature of human aspiration, the dynamics of psychological and spiritual change, the evolutionary trajectory of change, the relationship between madness and transcendence, the nature of subjective research, the transformation of social structures and the role of freedom, autonomy and relatedness in human experience including the ways which it can be used to deepen the quality of the educational experiences.