The purpose of this study was to investigate barriers women face when entering school administration as well as perceptions of the high school principalship held by female high school principals and assistant principals aspiring to the principalship. Work conflicts and job demands for women were explored as well as the significance of mentoring and networking along the pathway to the principalship. The information gathered through a critical feminist approach was used to assess women's barriers to the principalship and describe methods employed to overcome those barriers. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]