During the 150 years women have participated in higher education, they have made tremendous strides. At many postsecondary institutions, women were not accepted as students until the second half of the 20th century. In 2004, women serve in the upper echelons of power at some of the nation's oldest and most prestigious universities. This inquiry examines the history of women's participation in higher education, including their entry into leadership positions within the academy and the barriers and facilitators they experienced. The leadership models and the career development of women are also examined. The results of interviews with eight women administrators at postsecondary institutions in different states are discussed and compared. Challenges women face in the areas of socialization, leadership, and work-life balance are considered. The experiences and insights of women who have achieved leadership posts are also reviewed. Strategies and recommendations for women preparing to pursue higher education leadership positions are provided.