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In a time of increasing accountability, school leaders are besieged with challenges to improve their schools leading to a marked increase in principal turnover in recent decades. These conditions necessitate understanding how principals navigate professional transitions and the impact changes in leadership has on schools. Analyzing data from a seven-year study using a comparative case study approach this paper considers the experiences of one Catholic school principal as she transitions among three different school environments. Drawing on complexity thinking and the emergence process, the study explores the extent to which the principal was able to impact each school's readiness for change through processes of distributing authority and creating a common school vision, two critical features of a complex adaptive system.