At the end of compulsory schooling, young people face an important transition: they have to decide whether to pursue either further schooling or vocational training. Choices are crucial phenomena in transitions: they are based on what a person considers to be options and follow preferences shaped by their social position and context. Using a qualitative longitudinal interview approach, we explore the development of educational and occupational orientations from the last year of compulsory schooling through the two years after in Vienna, Austria. We subsequently develop a typology of young people's orientation processes over time: 'Determined', 'resigning', 'step-by-step aspiring' and 'drifting'. Taking the perspectives of young people seriously, we gain an understanding of thoughts, ideas and worries during this transitional phase. We also learn about institutional and social constraints and the resources that shape the orientation process and related patterns in time.