This essay investigates the discrepancy between the negative impact incarceration has on life outcomes and offenders’ subjective perception of incarceration as a positive turning point. Building on three years of fieldwork with 23 juvenile offenders in Boston and Chicago, this essay contends that the institutional structures of juvenile justice encourage the teenagers to frame their incarceration a positive turning point. At the same time, the punitive framework of incarceration restricts the young men’s ability to exercise creative agency in relation to their desired non-deviant identity. Consequently, they are unable to develop viable strategies of action that could sustain desistance after their release.