This case study explored a pedagogical reinvention and extension of Paulo Freire's popular education approach. To do so, the author drew on interview data with program participants and reflections of his own experiences as one of two adult educators in a yearlong Fellowship program for high school graduates. Relationships, relevance, revolution, recognition, responsiveness, and reflection all emerged as characteristics of teaching and learning within the setting. These emergent themes are presented as a six-pillar framework for liberatory teaching and learning, coined "a Pedagogy of Risk." As argued in this study, this pedagogical model may provide educators with a framework useful in creating more liberatory educative spaces that support students' critical readings and (re)writings of the world.