Information regarding school administrator quality, impact, and effectiveness exists in abundance (Bloom & Erlandson, 2003; Eagly, Karau, Johnson, 1992; Simien, 2005). There are few studies and research about the career development of Black female school administrators particularly and appropriate retention strategies that yield results encouraging them to remain in the field after having reported experiencing social exclusion and alienation while in their roles of leadership (Anderson, 1988; Tillman, 2004; Mertz & McNeely, 1998; Horsford & Tillman, 2014). Personally speaking, after having years of childhood experiences of social inclusion, I was unaware of what social exclusion felt like until I became an adult trying to navigate the world of educational leadership after having been a classroom teacher for four years. This study addresses my journey and its impact on how I viewed my early school administrator experiences as well as my decision to remain in the profession year after year utilizing autoethnography design. This dissertation research focuses on my K-12 schooling, early teaching, and school administrator experiences as a child evolving into the Black female identity, specifically in educational settings. I examine interactions of social inclusion and exclusion and their impact on my journey toward a career as a school principal as well as within my current daily job as an administrator. Utilizing the content contextual analysis strategy to triangulate participant narrative essays, journals, school year calendars, culture grams, and timelines, I found there were three prevailing global super themes that emerged repeatedly with multiple indicators. The three themes include (1) Being bothered or annoyed; (2) "Job as" expressing the functionality of my job; & (3) Advocacy for causes. I provide context for the role of social inclusion or exclusion in each global super theme as well as barriers to entering educational leadership for Black female school leaders. Critical Race Theory (CRT) is the framework I use to contextualize the autoethnography design and the inclusion of personal narrative as well as Participant Action Research (PAR) to identify the triumphs and barriers in my quest for leadership such as isolation, marginalization, and lack of support. The findings inform the coaching, training, mentoring, and strategies for retention which I recommend for Black female administrators by local education agencies (LEA) across K-12 spectrums. [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.]