Based on the results of transition studies in the UK, Germany, USA and Canada, the virtues of analysing the structural contexts, institutional arrangements and the young peoples' action orientations are presented. In the first decade of the twenty-first century, school and the labour market have become more and more decoupled and transition routes more uncertain. From a structural perspective, the sorting of school leavers into different transition pathways according to their educational achievements contributes to the reproduction of social inequality. From the actor' perspective, transition uncertainty requires that young adults develop agency (planful and adaptive competence) in order to manage meaningful decisions between alternative pathways to employment. By relating the concept of agency to intuitive rationality and biographical choice, various action strategies are presented that document how young people from different social origins actively pursue individual goals when choosing to follow or to change transition pathways. In contrast to an emphatic reading of the individualisation thesis, comparative transition studies show that only socially privileged and educationally successful youths succeed in transforming their agency into self-reflexive projects.