This article examines trends in learning among a multiracial group of activist urban educators in an inquiry group dedicated to the topic of structural racism. I find that deep learning about race and racism requires teachers to engage in risk-taking in 2 realms--conceptual and relational. Conceptual risk-taking involves grappling with ideas in new ways, while relational risk-taking requires educators to form deep relationships with colearners. These 2 realms of risk-taking are simultaneously discrete and interdependent. Together, conceptual and relational risk-taking strengthen teachers' potency in building personal and collective power to name and resist systems of racialized power and oppression.