This chapter explores and brings into dialogue the work of two ‘thinkers’ who were practitioners of social transformation living in quite different contexts but sharing a deep commitment to rethinking educational practice as a transformative force. Both Ivan Illich (in North and South America) and Chitta Ranjan Das (in Odisha, Europe, and India) developed extensive critiques of how human learning had been coopted for societal/political ends and both generated alternative visions of a humane and hopeful reclamation of such learning. The quotations above suggest one of the deepest basis for such a dialogue: Chitta Ranjan Das developed a sharp, critical contrast between “possession” or potestas and potentia or powerful possibility of human self-opening to other persons; Illich, for his part, contrasted “hope…in the goodness of nature”and the other person “as a social force”on the one hand, with the insatiable “expectations” created by the ‘Promethean’ process of human planning and control, on the other. In each case, critique aims to leverage open a path for social transformation through the blockages created by the long sedimentation of institutions and institutionalization upon learning.