Broadly, this dissertation study is an investigation of how mothers’ educational histories shape their parenting philosophies and behaviors and, through these intergenerational relationships, their children’s achievement during the transition to elementary school. Such an investigation is motivated by the life course paradigm as well as social capital theory and developmental research linking mothers’ and children’s educational trajectories through various parenting behaviors and strategies. Expanding upon this research base and the above stated research aim, the concept of diverging destinies highlights the importance of considering a specific set of life course pathways that are closely related to mothers’ educational attainment and their children’s achievement: employment and marriage. Thus, integrating mother’s employment and marriage into this dissertation study’s conceptual and analytic model, a second aim is to investigate how mothers’ education shapes the significance of women’s work and marital histories for their parenting and children’s academic trajectories. Findings from this dissertation provide support for the assertion that mothers’ and children’s academic pathways are linked through parenting. Findings also yield evidence for how mothers’ education augments the impact of marriage and employment on parenting and children’s achievement. Answering these questions has significance for sociological theory on the intergenerational transmission of advantage. / text