This thesis portfolio presents an autoethnographic account of a prison educator engaged in a research project that explores creative approaches to arts, prison education, work and training in custodial settings. The position of the researcher is located in-between and across professional practices including arts in prisons, prison education, work and training environments, which have conflicting agendas that, nevertheless, share the same institutional space. Policymakers and management bodies regulating these professional practices expect education and training to contribute to reducing reoffending. Procedurally, the research process was precariously balanced between, on the one hand, performing to measures of quality based on the requirement to reduce recidivism, and on the other, crude outcome measures driven by a utilitarian marketization of prison education that includes course completion rates calculated on the basis of minimum contact time. This broader context created an uncertain and constantly shifting context for the research, which began with my search for an effective creative practice in a Performing Arts Department (PAD) and ends in a Functional English classroom (FEC). Conceptually, the research draws on the What Works debate (McGuire, 1995; Brayford et al. 2010), which continues to create a disjuncture between policy and implementation resulting from unrealistic assumptions that arts and education programmes in prison might prevent reoffending, with evidence relying solely upon randomisation, reductive causation and numerical calculation. It also draws on desistance theory (Maruna, 2001; McNeil, 2006), which argues that desistance from crime can be understood as an indirect process, rather than an event. From an examination of my efforts to implement and develop creative approaches to education via autoethnographic tools, including fictional performative writing, I argue two main points. Firstly, the autonomy required by the creative prison educator engaged in an advanced research project re-positions the professional in a particular relationship with the bewildering processes of power, protectionism and performance management in the criminal justice system. Secondly, and as demonstrated through fictional performative writing, I argue that research methods engaging voices from the frontline of educational environments, can reveal seemingly small details relating to the challenges and possibilities of creative education in prisons that, nonetheless, have significant implications for developing productive and innovative approaches to desistance from crime. Moreover, from this grounded, yet restricted position, I speculate how such approaches might extend both creativity and creatively beyond the validation of this doctorate qualification.