This paper uses a life history approach to examine the decision making of six young people around what to do when leaving compulsory education. They all share similar social backgrounds and are located in one geographic place – a deprived, working class, urban area in the English midlands – but the six individuals have opted to follow three different post-16 pathways, even though they all achieved GCSE qualifications that would have enabled them to enter further education, and therefore potentially higher education. These different post-16 routes include employment without formal training (the workers), employment with formal training (the apprentices) and studying in higher education (the students). All the participants (and their families) are historically ‘rooted’ in the local area and this paper explores the influence of the social learning that takes place within local communities of practice – in the form of friendship groups, families and school communities – on the young people’s different, yet all resolutely local, early career trajectories.