In the business school context, informed by entrepreneurial discourse, failure is positioned as a generative experience which foregrounds learning opportunities. However, it is increasingly recognized that this discourse, which centralizes a heroic ‘triumph over adversity’ narrative, also produces pressurizing and harmful effects, for both management educators and students alike. This suggests an urgent need to explore alternative ways of thinking about failure. We do so by drawing on 31 semi-structured interviews with business school academics which explored their experiences of failure. Adopting an identity work lens, our findings highlight how business school academics are both regulated by, and yet also resist and refuse, dominant entrepreneurial discourses in their response to failure, engendering ambivalent and complex relationships between learning and failure. We make two contributions. First, we highlight the significance of limitations to attempts to learn from failure and their allied impotential responses, where both the incapacity to act and the capacity not to act, sit unashamedly alongside a capacity for repair. Second, we position this ambivalent response as a provocative space to move beyond prescriptions to simply fail better to instead fail differently. In turn, we consider how insights from management educators’ failures offer important insights for management education.