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This paper draws upon data collected from 20 working class, inner city pupils in a British (London) school (in Year 11, aged 15/16 years) as part of a research study exploring the ways in which young people understand their options and identities. Pilot study data is used to develop an analysis of the processes through which inner city, working class young people come to leave school at the age of 16. Attention is drawn to issues of identity and inequality within processes of leaving education. In particular, we highlight the ways in which the young people viewed themselves as 'not good enough' and 'knew their limits' in relation to post-compulsory educational routes. It is suggested that these views were constructed and compounded by complex social and institutional factors, and were exacerbated by educational policies that impact upon inner city 'failing' schools and disadvantaged communities.