This contribution takes the form of a reflective essay informed by 15 years of working and undertaking research with young people at risk of social exclusion and non-participation in the post-compulsory education and training system in the UK. In particular, it draws upon our experience of working with young people, youth workers and other adults in the "Engaging Youth Enquiry" undertaken as part of the Nuffield 14-19 Review. This research challenges two key policy assumptions: raising aspirations will lead to increased educational engagement and attainment and thereby reduced social exclusion; and that an alternative more "vocational" curriculum will improve young people's life chances. The work indicates a clear need to pay much greater attention to opportunity structures in thinking through policy interventions to support young people's transitions to the labour market. (Contains 1 figure.)