ABSTRACT Our paper proposes to rethink the concepts of modernization and modernity in the context of state socialist and postsocialist transformations in Eastern and Central Europe. By focusing on historical transformations, we seek to challenge normative and static constructions of the state socialist legacy and show that such perceptions are rooted in the Cold War ideological division. One way to contest this division is to reconceptualize socialist modernity. Drawing on James Ferguson’s seminal study on the “expectations of modernity,” we argue that modernization was central to the Eastern European Communist parties’ claims to legitimacy. While the state socialist experiment proved to be a failed political and social project, the dreams of modernity bereft of socialism continued to shape people’s self-images and social visions beyond the borders of “Eastern” Europe. In order to better understand the state socialist legacy and the political and social thinking of “postsocialist” people, we propose to link the study of the small transformations of everyday life with the critique of binary constructions of the concepts of socialism and capitalism.