Women are challenged most by cultural norms, particularly sex-role norms, religious and political ideologies, and gender-structured opportunities that favor men. Although some stereotypes have loosened a bit, dilemmas remain for women who aspire to fill school district leadership positions. The author's predicament is not unique. It is something many women (and some men) experience when they aspire to work in the superintendency or when they actually serve as superintendents. Now, as a professor, she has focused her professional growth on understanding the challenges for women that prevent their access to top levels of leadership in school district administration or erode their ability to lead. She refers to those challenges as "dilemmas" and to the consequences that are not favorable as "discarding." Dilemmas involving professional desires and other conflicting desires generally relate to one or more cultural categories. The examples presented in this article describe a dilemma for one woman (whose actual identities are shielded by request), yet the predicaments they faced will be familiar to many other women. Furthermore, the author states that in her investigations of the extent of women's support of other women in leadership positions, the most commonly expressed cultural norms have been these: (1) collaborative decision making wastes time; (2) women superintendents need to listen less and take stronger supportive action on behalf of employees; (3) women's public presence is not as strong as men's; and (4) women who have not worked previously with a female superintendent will critique her appearance, perceived failure to openly support female employees and inability to lead "the way men lead." Women generally have a better opportunity to gain their first superintendency in a rural school district where leadership is more personal. Although the number of women serving in the superintendency may be increasing, experiencing a woman's leadership as superintendent remains novel for many school districts.