In this project, panel data are collected on secondary school pupils in the cities Mannheim and Freiburg.  The aim is to observe their transitions from lower secondary school into higher secondary education and dual education.This dataset will make it possible to analyze empirically the educational career choices of pupils in the specific context of the educational system of Baden-Württemberg (including for instance the professional Gymnasium or the Werkrealschulen).A first research objective is to identify which socio-economic factors, skills and psychological traits influence the educational choices of secondary school pupils.Secondly, the comparison of the cities of Mannheim and Freiburg allows assessing the relevance of the local context on the educational choices. Thirdly, the effectivity of career orientation tools shall be assessed through a web-based intervention.Finally, we investigate the development of labor market relevant skills in the different types of secondary schools tracks.