This inquiry used autoethnography methodology in a self-narrative format that places the self within the position of a first time Superintendent as an African American woman. The design of this research will allow the reader to travel with me through my experiences to obtain information about the challenges and obstacles of the superintendent position. The study will focus on three dimensions of superintendent leadership, (a) Policy and Governance: Board and Community Relationships, (b) Organizational and Human Resources Management, and (c) Leadership and District Culture. The research design use of autoethnography, linked with the theoretical framework of Critical Race Theory (CRT), and sensemaking and sensegiving of organization management will allow for the examination of the dimensions of superintendent leadership through the experiences of the researcher. These dimensions will be reflected upon, analyzed, and interpreted within their broader social context. Implications and recommendations regarding further areas for study are provided. A basic premise of this study is that a relevant tactic to understand the work of public school superintendents is through the lens of superintendents. The purpose of this inquiry is to interpret a representative sample of my experiences as first-time superintendent over a three-year period. There is sufficient acceptance of autoethnography as a qualitative research methodology from which valuable conclusions and findings can provide helpful information to superintendents, particularly first-time African American women superintendents, who are committed to educational social justice. [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/en-US/products/dissertations/individuals.shtml.]