The catalyst for learning and change in transformative learning theory has mostly been explained in terms of a disorientation in a relatively stable life. This article explores a South African, nonformal adult learning program, as a source of "orienting dilemmas," which catalyze learning and change in lives that are regularly and repeatedly disrupted, such that disorientation has become normalized. The article opens a conversation about transformative learning theory in a postapartheid South African context, marked by high levels of violence, poverty, and inequality. It thus responds to critiques of the dominance of Western cultural values and lives in transformative learning theory literature and contributes to the theory in Southern, developing contexts, with greater recognition of the significance of context. The article shows how an early life of repeated disruption and difficulty can be transformed through emancipatory education initiatives. Such programs can introduce "orienting dilemmas," which catalyze transformative learning.