Progressive Education, with its pedagogical desire to engage students in a taught curriculum in a meaningful way, is often viewed in opposition to Conventional Education. In this conceptual paper, I argue that despite and even because of this opposition, Progressive Education contributes to the stability of Conventional Education by making Conventional Education bearable for its teachers. I claim that despite its institutional rarity, Progressive Education remains hegemonic among educators because of its promise of meaningful learning for all their students that can be achieved in and out of the conventional school settings. I provide a critique of Progressive Education from the Critical Dialogue Education and Democratic Education perspectives.