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This narrative study explored the transformative impact of collective reflective written and oral discourse regarding incidents of race and ethnicity. Additionally, the study sought to investigate how a deeper understanding of race, bias, and self, impacted educational leaders’ empowerment to support social action. Data collection included racial auto-ethnographies describing critical racial incidents, rational discourse conversations, and meeting reflections. Grounded in Mezirow’s (1991) theory of transformative learning, the “disorienting dilemma” themes identified through constant comparative analysis included geography, environmental influences, feeling seen and heard, and self-acceptance. The findings highlighted the transformative and empowering impact of shared racial discourse and reflection on educational leaders.