Between the two extremes of boredom and anxiety, we find space for flow: a calmer state of enjoyment in immersive, contemplative activities, which creates a loss of self-awareness (Csikszentmihalyi 1975). This paper draws on the research findings of two qualitative research projects about skydivers and performance artists to examine the phenomenological experience of flow. In particular, we focus on transitions in and out of flow, and examine their dramaturgical management in social interaction. The question of flow disruption is a marginal theme in Csikszentmihalyi’s work. This paper aims to develop this idea by exploring how and why the state of flow can be disrupted by critical self-awareness. Building on the existing research literature, we argue that flow is a harmonious yet fragile state of mind, which remains prone to restriction and disruption. Drawing on empirical data from our own research projects, we discuss the disturbances that occur when self-reflection returns during flow-generating activities.