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Although the early analytic literature includes discussions of the origins of driven, pathologically ambitious behavior (e.g., Freud 1916), the concept of ambition as an aspect of healthy development received little attention in the literature prior to the development of self psychology. Kohut (1977) assigned ambition a central role in his model of the bipolar self. He offered a powerful general theory for the evolution of nuclear ambition in early development and detailed various pathological distortions of the development of ambition in narcissistically damaged individuals. In this chapter, I will attempt to answer the following question: how does an established “self,” with the capacity for ambition, translate itself into a real-life history? In other words, what mediates between the cohesive bipolar self consolidated in childhood and the specific, manifest ambitions1 of the adult? I will take a particular look at the ambitions of women. The common experience of adult women today as they struggle to strike a balance between career aspirations and family commitments provides an opportunity to explore the topic of ambition more fully.