This dissertation develops and illustrates a theory of what I call transfigurative imagination. From both a conviction that the best philosophical thinking proceeds from singular cases towards generality as well as a personal interest in contributing to African philosophy, I situate the work in a contemporary African political context. The context provides a tangible instance of life which, through the fact of repeated failure of institutional politics and its effect on individual living, presents a breakdown of what both scholarly research as well as common wisdom assumes is necessary for wellbeing in a political context. Namely, the going well of the process of meaning making and the efficacy of political agency. I respond to this reality in four moves. The first two moves are diagnostic and descriptive whereas the last two are prognostic and normative. First, I provide a phenomenological account of individual existence in this context to reveal a faulty form of living which, because of the failure to make sense of life and to act efficiently, is always turned to an outside. I call this a pathological ecstasis, distinguished from the general ecstatic element of human life which requires an involvement in and concern for the world outside ourselves. Second, I show the specific ways in which agency fails, through a learned helplessness and inertia in public life and the relegation of minimal agency into the private life of friendship and family. Third, I develop the theory of transfigurative imagination, a form of imagination which, developed through an appeal to psychoanalytic theories of play and the literature on moral imagination, resets the project of meaning making by clarifying reality beyond the limits which are at the basis of the founding failure in living well. This perspective offers new ways to imagine what is possible beyond helplessness and to help us translate our imaginative visions into action. In a fourth move, I show the translation into action of this form of imagination by building an argument on the virtue of courage that draws from an Aristotelian tradition and moves away from it. Using the example of protest, I argue for a self-sacrificing form of courage as the form of political action appropriate to the context of political failure. I provide the justification of this way of life through an individual pursuit of wellbeing from a perspective of self-fulfillment. Whereas the Aristotelian tradition assumes the existence of a minimally well-functioning political community which both trains individuals into the virtues as well as provides a political context in which the virtues gain meaning, I present an argument devoid of these assumptions. Self-sacrifice, I argue, relies on individual pursuits of wellbeing, and is justified by duties to the self.