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This dissertation is part of the School2Work project and focuses on young people’s school-to-work-transition in the Dutch VET labour market context. The research follows students’ first steps within the labour market and considers a variety of characteristics and behaviours of individuals and employers to provide insight into the ways individuals and employers jointly affect individuals’ early job careers. The dissertation consist of four empirical studies, each of which focuses on different aspects of the overarching question. The empirical studies are embedded in an institutional and overarching theoretical framework and are based on the empirical analyses of two quantitative data sources. These data were collected among a group of VET students and employers in the Netherlands between 2011 and 2014. As such, this dissertation offers an empirical contribution to the scientific research on the school-to-work transition and meets the knowledge needs of policy and practice. The results of the empirical studies provide a number of important insights for answering the central research question of this thesis. First, this study shows that the transition from VET to the labour market is a lengthy process that has different routes and outcomes. The research shows that this process is less whimsical and unpredictable than is often assumed in scientific research. This study therefore partially supports the assumption that the transition from VET to the labour market is a long-term and dynamic process in which individuals become acquainted with professional practice and gradually build a career with high-quality jobs with one or more employers. Second, the research demonstrates that both individuals (suppliers of labour) and employers (demanders of labour) are relevant actors for realising a successful start to working life. Although including the characteristics and behaviour of both the individual and employer in the analysis appears to be relevant, the chosen interpretatio