In The Dialectic of Freedom (1988) Maxine Greene discusses the importance of naming the obstacles that stand in the way of enhanced possibilities. She makes pointed connections between education, private lives, and freedom, insisting that we remain vigilant about how “reality” is constituted and attuned to the socially imposed barriers that keep many from forming a more authentic self. “When people cannot name alternatives, imagine a better state of things, share with others a project of change,” says Greene,” they are likely to remain anchored or submerged, even as they proudly assert their autonomy” (9). I think of Maxine Greene’s words whenever gender becomes a part of my classroom discussion. Until they reﬂect upon what lies behind their unreﬂective beliefs about gender and the part it plays in decisions that inﬂuence schools, literacy politics, and their own emerging identities, students initially deem they have no serious concerns. However, once we begin to break apart what it means for schools to serve a student’s particular interests, needs, and desires rather than the school’s own demands for bureaucratic eﬃciency, dispassionate authority, and cultural tradition, such arguments begin to thin. Students start to recognize that they are tethered to a system that mostly allows only limited freedom, false choices, and little space for personal agency and growth. They begin to realize that they have assumed the conditions and roles of their education as something ﬁxed and ﬁnal rather than something still open, possible, and hence alterable. Because literacy is viewed in schools as something that is fairly predictable and measurable, students do not consider that what constitutes their developing young adult literacy may be quite diﬀerent from the literacies they were encouraged to embrace as children. It is at this point we can begin to talk about the authenticity of their school lives.