This article argues that "transition" offers a limited and outmoded conceptual frame for understanding young people's engagement with work and learning. It draws on two studies of young people to provide insights into the study and work experiences of older and school-aged youth. Our analysis suggests that rather than focussing narrowly on outcomes alone, transition should be seen as a process of identity development. Research on young people's perspectives reveals the active investment that they make to produce identities and foreshadow the emergence of new meanings of career. Four factors are especially relevant to this process: continuing inequalities; the contexting of choice; flexibility in decision-making and a readiness to make ongoing changes and choices and achieving a balance between goals of personal development and wellbeing and the continuing demands of further education and employment; and a re-definition of careers. We draw on our research to show that young people who are in school as well as those who have left school reflect a view of workplaces as sites of learning and identity formation. We conclude that new policy approaches are needed, which recognise the breadth (and depth) of learning that occurs across different sites in young people's lives, that challenge the dichotomy of "adult" and "youth", and that recognise the blurring of boundaries across formal and informal learning sites. (Contains 3 notes.)