How should Deweyan educators teach their students about engaging in efforts to bring about social change in a political context marked by polarization, power differentials, and oppression? In this article, Joshua Forstenzer argues that Deweyan educators must encourage their students to engage in pluralistic and creative experiments rather than teach a pre-set model for social change. To this end, he engages with two critiques: one formulated by Lee Benson, Ira Harkavy, and John Puckett according to which Dewey's pedagogic vision failed to be sufficiently practically minded; the other formulated by Aaron Schutz -- drawing on Saul Alinsky's theory of community organizing -- according to which Deweyan educators fail to be meaningfully politically minded, because their democratic faith blinds them to the role of conflict in real politics. In response, this article argues that the Deweyan outlook is closer to Alinsky's than Schutz assumes and that it demands that we Deweyan educators introduce our students to a rich diversity of voices and traditions that address the concrete conditions of social change to provide our students with a fullness of civic experiences, as well as a depth of political and social ideas to challenge the status quo.