Based on the findings of a ten-month ethnography of prisoners incarcerated in a British prison, this paper addresses how prisoners negotiate between two divergent identities, the criminal self and the work self to manage stigma. Two categories of prisoner are identified; the Not-for-Profit Criminal and the Career Criminal. Not-for-Profit Criminal embrace the work self to distance himself from the Criminal self; they draw on a hard-work ethic to avoid being deemed the ‘lazy criminal’. In contrast, for the Career Criminal, the two selves are intertwined- they are ‘hard working criminals’ and their work is their criminal activity. This research teases out the differences in prisoners’ strategies for managing stigma. They are not a homogenous group; how they respond, react and adapt their discursive strategies are different. This paper contributes to an understanding of how individuals navigate ideal worker images alongside stigmatised identities.