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This paper explores the power of Csikzsentmihalyi’s Theory of Flow and Optimal Experience for investigating whether the experience of flow in school leadership predicts factors bearing on retention in the profession. A “Flow in Leadership Inventory” was developed with items referencing components of flow in the work of school leaders, yielding a reliable composite measure of “Flow in Leadership” (alpha=.87). Forty-four (44) principals completed the measure as part of a survey of alumni of a university-based principal preparation program in the American Midwest. Results indicated that the composite flow measure correlated positively with the personal importance of career goals (r=.31, p<.05), and negatively with perceived misalignment of job stressors to leaders’ expectations and preferences (r=-.47, p<.01).