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Abstract: This study represents a nuanced investigation into how White principals confront and overcome resistance in their journey towards learning and implementing anti-racist practices in their schools and how their privilege and the political dynamics of the educational system rooted in Whiteness influence this process. Furthermore, we explore strategies used by White principals to productively navigate external resistance and confront their own complicity in maintaining White supremacy. Drawing from a year-long study of four White principals participating in a six-part anti-racist leadership design-based learning intervention series, we examine their collective effort to unearth White supremacy, dismantle racial injustice, build relationships, grapple with their positionality, and use their privilege to undermine Whiteness.