In August 2013 5.5 million young people were unemployed in the EU (EU 2013) many with low levels of qualification. However, as this study of nine Apprentices reveals it is possible to successfully progress through an Apprenticeship to work despite adverse prior educational experiences. Using open semi-structured interviews the research explored the Apprentices’ perspectives on their successful transition into the workplace; the social, cultural and emotional aspects, the unwritten and hidden curricula (Colley et al., 2003) that had underpinned their successful transition. The Apprentices describe how they had been able to develop a successful vocational habitus (Colley et al., 2003) through real-time rather than anticipatory socialisation (Evans and Heinz, 1994); a vocational learning culture where they had experienced and learnt to cope with responsibility: I’m getting like self-inflicted self-esteem... my self-esteem build up because I know that I’ve have responsibilities (Apprentice K) An argument made in this study is that young people who despite adverse educational experiences have successfully made progress into employment can be an important resource for informing EU and national policy and practice that aims to support the transition of vulnerable young people into employment.