In this article, the authors describe the use of phenomenology and thematic analysis to interpret raw data from interviews about the lived experiences of urban and suburban school African American administrators aspiring to the superintendency or another advanced school administrative position. The authors present overarching themes that capture the phenomenon of the lived-experiences of these administrators. Themes and findings are examined related to confidence, barriers, trust, and diminished aspiration. Recommendations are provided for further research to advance the opportunity for African American leaders to secure positions as school superintendents or other advanced administrative positions.