This paper draws on an oral history project which focuses on former coalminers' experiences of education and training. It presents the stories of five participants, all of whom undertook significant programmes of post-compulsory education during or immediately after leaving the coal industry and achieved a degree of social mobility over the course of their working lives. The paper compares and contrasts their experiences with those which now exist in Britain's former coalmining communities which, it is argued, have been substantively attenuated over time, especially for young men. Whilst it is evident that individual choice and motivation can play an important role in helping (or hindering) young people's journeys through education and employment, the central argument of the paper is that individual labour market success lies at the intersection of structure and agency -- although the data presented also demonstrate the extent to which opportunities available to young men in the former coalfields have been diminished by de-industrialisation.