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In this book, we have seen the diversity that existed between a large group of young men within a de-industrial community. I have argued that in a variety of settings, spaces and in different social interactions, multiple regions of masculinity are displayed by these young men. These contradictions highlight the pressures that an industrial and cultural legacy of a specific geographic area, places on young men to conform to ideals of manhood. This chapter further explores the issue of multiple aspects of self, with a detailed case study of one working-class young man called Jimmy and his transitions through post-compulsory education. I explore how the challenges of working hard academically and aiming to be a successful athlete are simultaneously met with other pressures to achieve a socially valued form of masculinity through engaging in risky leisure practices, such as drinking large amounts of alcohol. I …