With waves of reform initiatives rolling into schools from external sources demanding quotas and sanctions, how does a principal effectively reflect, assess, and learn from past reforms and day-to-day experiences? Studies of the urban high school principalship lack a "thick description" (Geertz, 1973) of the principals' hour-by-hour daily challenges and the way principals think about those challenges. The purpose of the study was to describe and analyze the urban high school principalship from an in-depth perspective of a principal involved in an intense high school reform effort at his school. The principal in focus is also the author of the study. This study utilized a qualitative exploratory case study design detailing, describing, and analyzing the principal's activities, thinking, and leadership qualities. The unique strength of the exploratory case study is its ability to deal with a full variety of evidence beyond what might be available in a conventional historical study. This study will add to the "neglected area of inquiry" of exploring the internal mental processes and practices cited by Leithwood (1988). The findings of this study, the in-depth description and analysis of the urban high school principalship, revealed clear themes of thinking, questioning, and confrontation of conflicts I experienced as a principal. The findings of this study identified two final emergent themes that captured recurring patterns of significance. They reflect the complexity of educational reform, not only in the pursuit of addressing high-stakes accountability measures, closing the achievement gap, and preparing students for college, but also in the developing thoughts in the mind of the practicing principal. It is important that, in the context of complex educational reform, principals would practice the discipline of deep reflection and critical analysis of their leadership practices to ensure they are leading schools where students are achieving meaningful learning. This research also serves as a springboard for further research and for informing the practice of those who are principals and for those who are preparing to be principals.