In this article we examine the experiences of transitions to work and the associated challenges for the agency of young people leaving residential care institutions in Luxembourg. We understand agency from a relational perspective as always produced in changing social constellations depending on the contextual conditions. In particular, state financing of care beyond full legal age in Luxemburg is linked to being in school or pursuing vocational training. This limits the phases and opportunities for trial and error and accelerates quick transitions into work by means of policies. On the side of the actors agency shows up as opportunities for action and as ways of influencing the own life. Our aim is to look at the vocational aspirations, hopes and intentions of care leavers in regard to a vocation and/or gainful employment during and after their transition from residential care. During transition it is important who accompanies and supports them (Arnau-Sabatés & Gilligan, 2015; Hiley, 2014). On the other hand, our aim is to shed light on how these adolescents and young adults experience and perceive transition processes and how they describe themselves in changing constellations. Where are problems or helpful reference points in coping with transitions? What effects do these challenges and references have on the future life choices and lifestyles of care leavers in Luxembourg? To answer these questions, the empirical analysis draws from qualitative longitudinal interviews with young people who were in the process of leaving care at the time of the research, as well as from retrospective interviews with young adults who had already left the child and youth welfare system.1 The inclusion of the two data sources makes it possible to gain insight into the unfolding transition processes and to take into account the experiences of care leavers from the perspective of a later point in their careers.