There has been an increase in the number of women serving as heads of school in independent schools, though women remain underrepresented as heads of school in large (> 700 students), K-12, co-educational independent day schools. Data in this qualitative study were gathered through interviews with six women who were current or retired heads of large, K-12, co-educational independent day schools. Using the 5D cycle of Appreciative Inquiry, journey stories were analyzed. In addition, the presence and types of journey partners, or advocates, were identified as well as the current mentoring practices of the participants. The study reinforces the presence of an intentional growth plan and encouraging advocates as essential aspects of the journey toward the headship. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]