Management learning aims to ensure managerial success and while failure is acknowledged, learners are encouraged to adopt a growth mindset and to bounce-back from failure. However, the complexity of contemporary managerial work and the degradation of the managerial labour process mean that managers increasingly experience failures. Managers therefore need to learn not merely from failure but to learn to tolerate failure, that is, to fail-well. The paper differentiates types of failures and focusses on intractable failures that leave managers feeling inadequate and that corrode their sense-of-self. Therefore, an affective and embodied identity-based understanding of managerial failure is developed and an empirical case-study of managers who engage in the most popular managerial sporting activity, running, is used to theorise the process of learning to fail-well. The mixed methods empirical study using artefact elicitation participant data and autoethnographic authorial data is detailed and suggestions for more reflexive managerial education are advanced.