The purpose of this research was to explore the worklife experiences and personal issues of female elementary assistant principals and examine the influence of these factors on their intent to remain in their position or leave. The worklife experiences and perceptions of female elementary assistant principals were categorized as institutional or professional experiences, or personal issues. A purposeful sample of 20 female elementary assistant principals from suburban, urban and rural school districts in Maryland, both public and private, voluntarily participated in the study. Ten subjects were currently employed as assistant principals and ten subjects had left the position. Qualitative findings from this narrative study revealed no single factor that solely determined the career path for assistant principals. Factors that were uncovered as being significant for assistant principals were relationships (both professional and personal), stress, support systems, personal lives, and family obligations. The female assistant principals who chose to leave their jobs were not significantly influenced by issues of gender, race, age or any other discriminatory practices, though these were present in their work. Recommendations from the study include (1) an examination of recruitment and preparation programs including internship experiences that provide hands-on experiences for aspiring leaders, (2) formal mentoring programs for assistant principals, and (3) meaningful professional development practices. [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.]