Early intervention programmes are designed to address complex inequities for Canadian families living with low income, affecting social relationships, well-being and mental health. However, there is limited understanding of resiliency and change in families living with low income over time. We conducted a mixed methods study with recent immigrant, other Canadian-born, and Aboriginal families living with low income, who attended a two-generation preschool programme (CUPS One World) between 2002 and 2008. The aim of this study was to develop an understanding of the processes of change. We included 134 children and their caregivers living with low income, and experiencing mental health problems, addiction or social isolation. Children's receptive language, a proxy for school readiness, was measured at programme intake, exit, and age 10 years using the Peabody Picture Vocabulary Test 3rd Edition (PPVT-III). In Phase I (quantitative), we identified children with receptive language scores in the top and bottom 25th percentile, informing participant selection for Phase II. In Phase II (qualitative), we engaged in constructivist grounded theory to explore experiences of 14 biological mothers, after their children (n = 25) reached age 10 years. Interviews were conducted between June and September 2015. The core category, Stepping Stones to Resiliency, encompassed Perceptions of Family, Moving Forward, Achieving Goals, and Completely Different. Perceptions of Family influenced families' capabilities to move across the Stepping Stones to Resiliency. Stepping Stones to Resiliency provides a lens from which to view others in their daily challenges to break free of painful intergenerational cycles. It is a reminder of our struggle, our shared humanness, and that movement towards resiliency is more difficult for some than others. Our findings challenge traditional episodic, biomedical treatment paradigms for low-income families also experiencing intergenerational cycles of mental health problems, addictions, social isolation, and family violence.