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The aim of the paper is to examine current and evolving supply side transition policy initiatives in the light of (a) particular demand side needs of urban young people classified as those most disadvantaged and potentially marginalized; and (b) the emerging realities of accessing and operating within particular examples of high value-added knowledge work arenas of the new urban economies in the UK. The paper is a synthesis of qualitative research undertaken by the author over the last five years that has examined notions of transition, development and learning for both young people and adults as they attempt to navigate their pathways in, and through, the new economies of the post-industrial urban context. The paper communicates the importance of a number of sociocultural theoretical concepts as a way of illuminating transition choices, actions and opportunities for disadvantaged young people. These concepts also enable a broader set of critical questions to be asked about current 14-19 transition policy and practice, particularly with regards to Connexions and the Careers Education and Guidance in England 11-19 National Framework.