This paper explores the dilemmas women face when they strive to achieve. It is about why women have trouble with their own deeply held ambitions, how patterns of interaction with important others are internalized in their childhood years that render their own strivings for power unacceptable to them, and how this early sense of prohibition against achievement is reinforced by the larger social and cultural surround. I contend that these interdictions against success are held by the female both in and out of her awareness, and are evoked in situations that trigger pathogenic memories in ever more complex ways. I explore current concepts about gender and gender formation, in particular the ideas of Adrienne Harris articulated in her book, Gender as Soft Assembly. Two clinical cases are described in order to explore and illustrate these issues, one a child and the other an adult.