The focus of this study is on examining the role of an educational leader through the process of developing and implementing a community school. As the primary researcher, I sought to contribute to the body of community school research by identifying organizational roadblocks, leadership perspectives, political influences, and whole child development while highlighting the importance of creating an environment capable of addressing the needs of children. Through this account, I seek to describe the importance of developing community schools and how their creation in similar circumstances might be facilitated. I sought to gain an understanding of the process of developing a community school through my own experiences. For this purpose, I reviewed key moments that guided me in the past three years as principal at a public middle school. I collected data primarily through field notes, electronic communications, calendar events, recollections of conversations, and observations of my own lived experiences. The findings of this study reveal the complex and turbulent nature of implementing sustained change in a school setting. Key components of this study include my introspective investigation of compliance, tenacity, child development, and the purposes of education. A rich account of my development is included to help aid those attempting similar changes. Findings also include my personal development as an educator, leader, and researcher relevant to implementing a community school at a public middle school. Human development and cultural capital are investigated in this study, providing further insight to my journey in ethical and moral decision-making surrounding these changes.