Only a limited number of resilience studies report what challenges and enables adolescents living in townships. Even fewer report the aforementioned from the perspective of adolescents themselves. Given that resilience is a contextually and developmentally sensitive process, it is an oversight to marginalize the risk- and resilience-related insights of township-dwelling adolescents. We correct this oversight in this article. To this end, we report a grounded theory study with 17 South African adolescents (aged 17–19) who generated visual and narrative data. Two core insights emerged. First, parental expectations underpin adolescent disillusionment. Second, empowering women (i.e., mothers, woman relatives and/or woman teachers) are key to how adolescents adjust well to the aforementioned challenge. These insights, which extend what was previously understood about the risk and resilience of township-dwelling adolescents, fit with social ecological understandings of resilience and offer useful leverage points to champion adolescent resilience.