The Australian Government's efforts to increase the proportion of Australians with university-level qualifications has placed educational aspirations at the forefront of education policy. Despite increasing numbers of young Australians enrolling in higher education, regional and rural students continue to be underrepresented in university populations. Previous research shows that levels of social capital are positively associated with educational aspirations; therefore, in this paper, we examine the associations between access to various forms of social capital and aspirations for post-school study and employment. We conduct analysis of data collected from 460 students attending government secondary schools located in and around Shepparton in regional Victoria. Of the various measures of social capital, we focus on parent-derived social capital, discussions with parents; student-derived social capital, participation in extracurricular activities and peer-derived social capital, aspirations of their friends. We explore how measures of social capital can be used to critically make sense and engage with the post-school aspirations of young people in the increasingly precarious landscape of youth employment in the twenty-first century.