Abstract: Youth educational transitions have transformed since the 1970s, in response to dramatic changes in the labour market and associated policy shifts in relation to post-compulsory education. Assumptions in current youth and education policy of linearity and choice in educational transition, however, do not match the practice of this transformation. This article challenges both these policy assumptions by drawing on the experiences of students at two Senior Colleges in the state of New South Wales. Findings suggest that non-linear transitions may be beneficial and represent successful attainment of adult status. Furthermore, individual choice was found to be restricted by external factors, including actions by adults, schools and systems. The presentation of research results in this article aims to contribute to a reconceptualisation of educational transition, in order for policy to better match transition experiences in contemporary society.