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We examine the types of risk that organizers seeking to build people-based political power take and describe how organizers cultivate habits of courage in themselves and others to regularly confront these risks. While prior literature emphasizes the degree of risk (high vs. low), we identify and elaborate two qualitatively different types of risk: internal and external. Drawing on in-depth interviews with 88 movement organizers in six states, we found that organizers operating in different issue domains and geographies all cultivated three practices to confront risk: (a) confronting painful experiences to overcome feelings of powerlessness, (b) mastering their own stories and vulnerabilities as a necessary precondition to recruiting others, and (c) holding themselves and others accountable to public commitments.