In this paper, we consider how recent social changes in the United States may be affecting vocational decision making. While adolescents often maintain high educational and occupational aspirations, the transition from school is characterized by few institutional supports, the prolongation of education, and a multitude of options with respect to the combination of school, work, and family. In such a context, what themes characterize decision making about schooling and occupational careers? We draw on qualitative interviews collected as part of the Youth Development Study (n = 1000), a longitudinal study of work through adolescence and early adulthood. Multiple themes were identified including unfulfilled expectations, the postponement of decisions, turning points that crystallized decisions, and resources and obstacles including, among others, family, work, school counseling, and teachers. These themes characterize contemporary occupational decision making and thus would be appropriate focal points for future research. They also suggest that social policies may need to be modified to facilitate the young people's quest for vocational identity and work.