ABSTRACT Securing stable, well-paid employment has become increasingly difficult for youth world-wide, negatively affecting their health and wellbeing. In recent years, this job insecurity has been exacerbated by compounding natural, economic, and social disasters. At the same time, young people are increasingly being encouraged to pursue higher education to secure a more viable future. This paper examines the post-school transitions of 22 Australian school leavers who were interviewed while at school between 2012 and 2017 and then again 1–5 years post-school. We investigated their transition into work and/or further education in the light of (1) profound societal change, and (2) the dominant narrative of university as necessary for the “good life.” We found that young people face immense pressure to attend university, even if their career aspirations do not require a degree, while other post-school pathways are derided. This pressure can compound stress and mental ill-health and is exacerbated by the limited career education available to students during schooling. In the context of immense transformation in contemporary society, we argue that conceptions of “worthy” post-school pathways must be broadened and communicated to young people through high-quality career education as they navigate their post-school transitions.