Some parents and educators think about issues of identity and cultural differences, and they wonder "how long they can delay" the conversation with their students because they do not want to introduce concepts that might be too complex or challenging for young children. Others think about issues of identity and cultural differences and wonder "how quickly they can begin" the discussions with their students and children, because they want to equip children early with the tools and language they will need to navigate and thrive in a world that responds to their identities as much as to their abilities. As the father of two young African American boys, the author knows the challenges that await his sons, whether their actions warrant them or not. Running from conversations about race because we would rather avoid than risk offending, or shifting the context to other identities because we find them easier to discuss, will not save any of us from the challenges and dangers of racial injustice. Once we open up the conversation, we begin to increase understanding, mitigate guilt and blame, and help people feel better about themselves and their work. Parents are more effective in their parenting; educators are more effective in their teaching; and children are better off for both. In this article, the author discusses the importance of learning the skills to discuss issues of race. He explains why understanding concepts such as white privilege and white supremacy are necessary to interrupt and arrest systemic injustice. Making the shift from values to skills does several things in the effort to form a more perfect union and school community: (1) It provides a framework to avoid mistaking identity for skill and confusing caring for competency; (2) It increases the level of access that we all have to this effort; and (3) The shift holds all of us accountable and disallows any of us from opting out, believing the work and responsibility belongs somewhere else to someone else.