Unprecedented developments in the Australian labour market and youth policy since the 1970s have contributed to making completion of senior secondary education increasingly common, and expected in youth policy. In this changed context, issues to do with educational marginalisation and youth transition need to be re-conceptualised. This paper is based on research carried out at two Senior Colleges in the state of New South Wales in Australia, both aimed specifically at providing re-entry opportunities to complete senior secondary education. Findings are drawn from interviews with students and teachers, observations and documents. This study contributes to challenging conventional policy discourses in relation to the concept of youth transition by focusing on a non-typical cohort of young people. Most of the students had experienced difficulties in their schooling, and many had been absent from education for some months or years before enrolling in a Senior College. The research findings highlight the impact of societal change on marginalised young people in relation to non-linear pathways, choice biography, and the knowledge economy. The paper concludes by exploring the impact of the 'biased' sample of young people on the meaning of these findings.