In Australia, the relatively low standing of vocational education and the occupations it serves is of growing concern. This standing is held to contribute to an increased number of young people preferring to engage in higher education and to look past vocational education as a potential post-school pathway. Consequently, there are skill shortages in some occupations, as young people who might be suited to them are now completing university degrees instead, including those with no clear alignment with occupations or employment outcomes. To redress this imbalance, it is necessary to identify factors shaping young people’s decision-making about post-school pathways and preferred occupations. The findings of a project investigating these factors and how they might be addressed are presented and discussed here. Central are interactions with familiars, including parents, teachers and peers. However, the degree by which interactions are informed, engaged and influential differed. Teachers may need to be impartial and students’ deliberations about post-school pathways more widely informed. Strategies to achieve these outcomes were evaluated by informants, leading to suggestions for policy initiatives. These included government’s role in championing vocational education and how schools might more effectively inform and support students’ decision-making about post-school pathways.