Recent historical studies on the origins of the postsocialist order in eastern and central Europe have adopted a “long transformation” perspective. They emphasize the importance of state socialist economic and political experts who, as early as the 1970s, began to think in ways that would prove compatible with neoliberal governance after 1989/91. Sharing this interest in longer genealogies of the postsocialist transformation, the present article shifts the focus of attention from the history of expertise to the everyday practices and “work on the self” of members of the urban and educated classes. It presents a microhistorical study of courses for students and white-collar workers that were offered by psychology coach David Gruber from the 1980s in Czechoslovakia and focused on intellectual productivity skills such as speed reading. These courses provide a unique insight into how people worked on themselves to become more effective in order to adapt to the newly emerging postsocialist world. The present article points to hitherto understudied continuities in the understandings and practices of productivity between the socialist and postsocialist periods.