For many Cape Flats communities in the Western Cape Province of South Africa, gangsterism defines the dominant culture. How the state of wellness in such communities influences decisions that individuals make, and the choices that are available to them when faced with hardships, violence-related trauma, and socio-economic crises, seldom seem to be part of the research agenda. Limited research has been conducted on the well-being of the youth who grow up in gang-infested areas. This article reports on research that sought to develop a critical understanding how the childhood experiences of township youth influence their decisions to become gangsters. The findings shows that decisions that township youth make cannot be separated from their community’s social disorganisation. Gangsterism formed a safe backdrop to childhoods characterised by a lack of personal validation in families, scarcity of suitable role models and personal economic deprivation. The street gang provided the stability and validation that was lacking in their home environments. However, in adulthood their uncritical acceptance of the gangster lifestyle is challenged. The research found that critical incidents in their lives force them to re-evaluate their childhood decisions. It is when critically reflecting on the meaning of their lives that decisions to leave the gang occur.