Chapter 6 provides an overview of psychoanalytic views of female ambition. Starting with Freud, psychoanalysis has had a long history of viewing female ambition from a perspective of deficit, rather than the capacity for the healthy pursuit of one’s dreams. Despite this ambivalent and phallocentric lens, psychoanalysis has also offered revolutionary understandings of women and what they want. This chapter will explore the history of psychoanalytic ideas about women and ambition, including a review of the transformative contributions of several important female psychoanalysts. A review of the history of psychoanalytic ideas about women and ambition is presented in the socio-cultural context of both the women’s movements and the 2016 presidential election in the United States. Postmodern ideas about the role and intersection of socio-cultural influences are highlighted, including a call to re-think our theories about female ambition in light of multiple female identities, rather than a monolithic approach to women’s ambitions.