This article reports on qualitative research with Alan, a former resident of the therapeutic communities at Her Majesty’s Prison (HMP) Grendon, England, exploring narrative identity beyond therapy. The study emphasises the complexity inherent in the five identities on which Alan draws—the Achiever, the Liminal Man, the Lucky Man, the Puppet, and the Wise Man. We suggest that narrative identities are adapted and reconstructed as they are taken outside of the therapeutic community into a less supportive social environment. This process continues to present challenges for the ex-resident, who may struggle to reconcile the redemptive identities nurtured in therapy with condemnatory ones that have echoes of a criminal past, which may be reignited by personal and social circumstances.