Abstract: The school to work transition in Central and Eastern Europe is a highlighted research topic because of the market transformation. The article investigates graduates from tertiary education from the perspective of their human capital investments, labelled as ‘double status position ’ when students study and work at the same time and acquire work experience during their studies. The article distinguishes two forms of this activity: study-related and non-study-related work. Data used in the article come from recently available data sets, which surveyed respondents who had graduated from tertiary education five years prior to the projects. A broad range of Central and Eastern European countries are analysed in this study. The data contain retrospective information on studies, work activities undertaken while studying, as well as on parental education. Two research questions are studied in the article. First, the salience of the double status position is compared. Second, the influence of work activity during study on entry into the labour force is investigated using two dependent variables: the length of time graduates needed to find a job and the quality of the first job in terms of a good match between education and work. Multivariate regression models are applied to study the research questions. Results reveal that the occurrence of double status positions for graduates is in line with institutional transformation, and with the deregulation of the tertiary education system and the labour market. The impact of the acquired work experience also varies by country and depends on institutional and individual features.