Current scholarship tends to frame retreat-going, and the practices carried out therein, as emblematic of late-modern forms of self-work, understanding retreats as part of broader personal life projects of self-mastery and self-knowledge. For this article, I draw on empirical data to suggest that, although work on the self is typically the central concern for retreat-goers, they also question or outright reject the discipline of the retreat space by breaking its ‘rules’. Borrowing insights developed in the context of organisation studies, I describe two kinds of such ‘misbehaviour’ on retreat. First, I explore how retreat-goers misbehave in regards to the rules around intimacy, since sexual and erotic desire is usually discouraged but nonetheless features in retreat-goers’ experiences. Then, I explore examples of collective misbehaviour and suggest that retreat-goers often work together to ensure the retreat’s success by collaboratively breaking the rules through practices like gossip. This article contributes an understanding of how wellbeing practices might be usefully made sense of as social accomplishments, situated within the greater swathe of everyday life. But I also map out one way in which the concept of ‘misbehaviour’ might be applied to activities outside of the workplace.