This chapter critically reflects on my experiences of education, work and social change in Doncaster, a deeply unfashionable post-industrial city located in Britain’s former central coalfield where I was born, grew up, and continue to reside. Whilst my journey has not been smooth or straightforward, I recognise that I have, overall, benefitted greatly from education, it is also important to point out that education has often been the site of ridicule, failure and humiliation for working-class pupils and students. De-industrialisation has moreover further complicated the relationship between education and employment and has, I argue, attenuated many of the opportunities which previously existed for young people living in working-class communities, particularly young men, especially if they are not able or prepared to leave their immediate surroundings. Whilst such processes are evident across many post-industrial locales they are, I suggest, felt especially keenly in former coalfield towns where educational success is increasingly associated with the loss of talent set against a labour market now disproportionately characterised by ‘poor work’. The consequences of all this are, I argue, profound and can be seen as a significant contributory factor in the ‘unmaking of the English working class’.