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The tenets of self-determination theory (Ryan & Deci, 2000) were used to ground this qualitative investigation into school leaders' motivational dispositions in climates they perceived as controlling or autonomy-supportive. The participants were 15 kindergarten-12th grade principals from a western state. A semi-structured interview protocol was used to understand the motivational dispositions of the participants through various aspects of the principalship. Three themes emerged from the data: (a) knowing thy self: intentional actions, (b) keep and delete: pausing to reflect, and (c) not losing your “true self.” The findings provide insight into the how the field of educational leadership can continue to develop better ways to support aspiring/current school leaders when they are navigating climates that range from controlling to autonomy-supportive.