This paper takes a micro look at the challenges and successes of a CEO/Director of Education as he attempted to lead as a “new theoretician” whose theories were lived in action. It explores the actions and reflections of one theoretician--a CEO/Director of Education--who attempted over a five year period to employ the available evidence and theoretical frameworks related to leadership and organizational change to improve student learning throughout his district. While the application of emergent leadership principles as outlined in our paper have been associated with successful school change and improved student learning, we have found that they lack the specificity that is needed to guide the actual practices of a district CEO/Director of Education who is responsible for the administration and leadership of a complex organization. This paper reports on our analysis of such practice as one district CEO/Director of Education navigated through multiple challenges and self-doubt while on a journey to systemic improvements throughout a school district. Results of our research will contribute to the development of a deeper understanding of how district leaders can put theory into practice in order to better influence student learning. The primary data source for our analysis is the CEO/Director of Education’s journal, his personal reflections, together with in-depth interviews and aggressive interrogations of his actions and thought processes conducted by a university researcher who acted a participant observer in many key activities as a university partner. Other data sources include interviews, observations of meetings, and survey data.