This contribution presents results of a longitudinal qualitative study of young adults with different career plans and transition pathways. The central question of this study focuses on the relevance of vocational orientation programs at regular schools for young people’s career plans and transitions. The first part deals with the organization and research about vocational orientation programs. The second part begins by giving an insight into the empirical design of the longitudinal study. It then proceeds to discuss how the methodological perspective of reconstructive research can provide deeper understanding of student’s perspective. Narrative interviews are used as the basis to investigate how the socialization contexts are relevant and interconnected. Through the deeper understanding of student’s perspectives and the role of different socialization agents, it is possible to highlight the relevance of vocational orientation programs at schools. The findings could prove useful for improving vocational orientation programs at schools. Currently, such programs are disconnected from students’ everyday life and show little regard for their perspectives.