Engaging Paulo Freire’s Pedagogy of Possibility is a cross-cultural case study of how people experience schooling in relation to their sense of time and optimism. Csar Augusto Rossatto examines how real-life situations and social structures influence people’s construction of notions of possibilities. Positionality, or perceptions about life and projections of the future, has great impact on students’ success in school. These perceptions-how they interpret the past, live in the present, and foresee the future-are, in turn, greatly influenced by their intellectual locality. By the same token, how educators see their position in the world and their classroom ‘roles’ determines their operandum beliefs. The findings of this study suggest that a curriculum based on Freirean critical pedagogy and time theories can be used to enhance time-consciousness values in contemporary social life.