School systems have been faced with the attrition of male educational leaders in school districts. In particular, male educational leaders in the Maryland school district are pursuing non-educational leadership career paths instead of educational leadership career paths. Thus, the purpose of this qualitative, descriptive phenomenological study was to explore the lived experiences of male educational leaders in the Maryland school district who chose to pursue non-educational leadership career paths instead of educational leadership career paths. The conceptual frameworks that guided this study were Rogers's concepts of ideal self, self-image, and self-worth and Dawis and Lofquist's concepts of personality, need, and ability. The overarching research question addressed the lived experiences of male educational leaders in the Maryland school district that might have influenced their pursuit of non-educational leadership roles. A purposeful sample of 20 former male educational leaders of the Maryland school districts shared their lived experiences through open-ended telephone interviews. Data were collected using an interview protocol and audio recorded interviews. Collected data were manually transcribed and coded. Interview transcripts were uploaded into the NVivo 1.3 software application. Data were analyzed using Giorgi's descriptive phenomenological method. The findings revealed six thematic categories: job satisfaction, positive feelings, neutral feelings, negative feelings, challenges of educational leadership, and lessons learned. Findings may contribute to positive social change by providing school systems a better understanding of developing gender diversity initiatives that address critical issues and needs from educational leadership experiences. Such understanding could be used to increase male educational leader job satisfaction and decrease their turnover. [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.]