For journalists, policymakers, and scholars, Belarus has been interesting first and foremost as a case of “the last true dictatorship in the heart of Europe”. The repressive political environment in Belarus has been presented as overwhelming and has been examined with abundant references to the country’s “derailed” historical development, the “weakness” of its national identity, and with close attention to the biography of President Aliaksandar Lukashenka who is in power since 1994. The current study is an attempt to change the perspective under which Belarus is usually studied. Instead of looking at the country from a safe distance, it delves deeper into the texture of the social life by exploring the micro-level of personal experiences. The project examines the careers of Belarusian scholars belonging to a cohort who started their undergraduate education in the early 1990s. The cohort is divided into three subgroups of stayers, leavers, and returners, as well as into hard and soft disciplines, and male and female gender groups. The sample comprises a minimum of five interviews in each subgroup (67 interviews or 110 hours of audio recordings in total). Collecting retrospective data via in-depth semi-structured interviews, I focused thematically on professional careers to compare and contrast differences and similarities of the life courses within a single cohort. The semi-structured nature of the interviews brought order to the biographical data and allowed the comparison of life trajectories and life events of individuals. Looking back on their professional careers, the participants were able to reconstruct their personal experiences of main institutionalized transitions like from school to university, from university to graduate school, from graduate school to the defense, from the defense to a stable employment, emigration and return migration to Belarus. Instead of looking at a career as a result of individual achievements and characteristics, my approach is to explore individual agency and how it is limited or boosted by contextual opportunities and constraints. Focusing on the relationship between structure and agency, the project strives to determine the agency as well as the nation-specific opportunity structures in the domain of higher education. The qualitative data helped gained access to the motives, interests, and orientations as well as action strategies of individuals in their life course transitions under the conditions of social change.