In this paper, educational pathways emerge from the nexus of ancient narratives and future possibilities. Such imaginings are as much attributed to the African American intellectual tradition as to contemporary Afrofuturisms, including those born in histories of Blackness. The overlay of what was and what is not yet is significant because it engenders educational potentialities that are central to aesthetics and onto-epistemological wonderings. The author uses seminal dialogues from scholars like Sojourner Truth, Mary McLeod Bethune and Anna Julia Cooper as a springboard for envisioning Afrofuturisms in which schooling functions to transgress the assemblages of violence and capital of shame that pervade classrooms and corridors contemporary education. Not unlike the call of Sylvia Wynter, Sun Ra, bell hooks, Octavia Butler and other Afrofuturist activists of the feminine, this paper (re)imagines schooling from the roots of its past and the future conditional they portend.