Popular education depends on the embodiment of democratic leadership and a pedagogy for liberation, where dialogue and critical reflection empower adults to become change agents rather than passive participants in disenfranchising practices. Most colleges and universities in this country are organized by hierarchies of power and control. There is a fear-based helplessness in students that is cultivated to maintain those hierarchies, and the lingering effects of passive schooling are evident in adult students who are resistant to active engagement in complex cognitive processes. Given that teachers, as well as students, are a product of this educational culture, where do educators learn a pedagogy grounded in participatory, democratic ideals that empowers adults to effect change in their personal lives, communities, and society? Popular education is driven by leadership that creates learning opportunities designed to replace helplessness with authentic empathy, courage, and action. The critical classroom can provide a space for the process of examining assumptions, anchoring relevant theory into current contexts, and transferring learning into personal and collective change. This article discusses steps to creating an environment that promotes the expansion of education beyond the classroom to a critical exploration of society. That transfer of learning will generate the future narratives of popular education.