Although teenage mothering has been exhaustively studied, the cross-sectional designs and the deficit-finding focus of empirical-rational studies have exaggerated the negative consequences of an early pregnancy and have obscured how teenage mothering is often a rite of passage to adulthood, particularly in the absence of middle-class resources and aspirations. In examining the experiences of young mothers, an 8-year longitudinal study sought to understand how teenage mothers extend and develop family caregiving traditions. The original sample included 16 families and 39 subjects. Multiple individual and family interviews were conducted once the teen's first-born infant reached 8 to 10 months of age, and then 4 and 8 years later. Data from all three study periods were analyzed using the interpretive method. The following analysis provides an in-depth account of how young mothers with an oppressive past strive to become the parents they want to be. In addition, the teen mother's difficulties and struggles of creating a more positive maternal legacy and the role that positive and negative examples of parenting play in fostering or hindering the development of a new caregiving tradition are described. Study findings have implications for how clinical practice and social policy can better assist mothers to become the mothers they want to be.