Whiteness and white supremacy culture were created by groups and are maintained by them. When white people come together to unlearn and challenge the systemic effects of whiteness, we can begin to dismantle white supremacy in ourselves, our schools, and our communities. Alone, white people (and educators) become overwhelmed, complacent, and distracted. Together, we find energy in shared learning and courage through shared vulnerability. Scholars, great thinkers, and educators of color have explained for centuries that white people have important work to do together to understand and address whiteness. And yet, creating and sustaining conversations about whiteness and what it means to be a white educator pose real challenges. Questions about how we draw people into the conversation, sustain the dialogue, and address the inevitable pitfalls of talking about whiteness quickly emerge.