Vocational decisions in compulsory school define starting points of professional careers. At the end of apprenticeships, prior vocational decisions can be changed. Prior research shows that the motivational expectancy-value-theory explains educational decisions when moving into a dual apprenticeship and when moving from an apprenticeship to work. We hypothesize that expectan-cy-value theory allows a prediction of educational versus occupational career choices in varying career situations. We chose a multi-cohort cross-sectional design and applied standardized online questionnaires to examine these hypotheses. The sample consisted of three cohorts: (1) 472 9th graders, (2) 716 apprentices at the end of VET. The online questionnaires consisted of items with rating scales that were successfully developed in prior studies. Results from path analyses show to what extent student expectancies and values in two different age cohorts predict the choice of an apprenticeship or an education. The results contribute to our theoretical and empirical knowledge about the transition from school to work, so that we can learn how adolescents make vocational decisions at different stages in their lives. We discuss how the results let us improve the regulation of the VET system in Switzerland.