Despite the supposed rehabilitative function of incarceration, individuals who spend time in prison are often viewed narrowly as ex-offenders. However, framed contextually, their stories can illuminate factors with far-reaching implications. The purpose of this critical narrative inquiry was to provide a shared first-person account of a Black man living in postapartheid South Africa. His told experience included stunted maturation because of early incarceration and overcoming stigmatization upon reentry into his community. Interconnected social systems including education, employment, and community infrastructure affect quality of life for generations. His story sheds light on structural and individual barriers and the resilience needed to navigate them.