Educators increasingly extol failure as a necessary component of learning and growth. However, students frequently experience failure as a source of fear and anxiety that impedes risk-taking and experimentation. This essay examines the dissonance between these "generative" and "stigmatized" paradigms of failure, and it offers ideas for better negotiating this dissonance. After conceptualizing the two paradigms, I examine various factors that reinforce failure's stigmatization. I emphasize "precarious meritocracy," a neoliberal ethos driven by hypercompetitive individualism that makes success a zero-sum game, and that causes especially significant harms on students who are already socially stigmatized. Efforts to ameliorate paradigm dissonance tend to focus on changing student dispositions or lowering the stakes of failure. I instead propose "wise interventions" that include analyzing the systemic roots of stigmatized failure and making failure a more communal experience. I then briefly address the systemic transformations necessary to cultivate generative failure more broadly.