Policymakers concerned with raising school completion rates and broadening entry to higher education have pointed to the variations in education and career aspirations across different groups and communities in Australia. The view has been that depressed aspirations in parts of the Australian population contribute to differences in outcomes. However, the links between aspirations and educational and labour market outcomes are not well understood, nor is the role of aspirations in the negotiation of school, course and pathway choices. This study uses data from the longitudinal surveys of Australian youth (LSAY) to look at aspirations of 15 year-olds and how they change and are fulfilled or not as students progress through school and beyond. One of the most valuable and significant features of LSAY is its longitudinal focus, allowing the development of a complex picture of young people’s transitions over a decade (from the age of fifteen through to 25), tracking changes in attitudes and expectations together with the nature and quality of participation and engagement with school, training, work and higher education. We examine the effects of student background characteristics (including demographic, geographic, and socioeconomic characteristics), school features and practices, and curriculum and program opportunities on aspirations and outcomes.