This chapter offers a detailed consideration of how theory can support deeper understandings of teaching artistry, focusing on the concept of engagement within the framework of flow theory [Csikszentmihalyi, Creativity: Flow and the psychology of discovery and invention. Harper Collins Publishers (1997), Flow: The psychology of optimal experience. Harper Perennial Modern Classics (2008), Applications of flow in human development and education: The collected works of Mihaly Csikszentmihalyi. Springer. https://doi.org/10.1007/978-94-017-9094-9 (2014)]. The chapter outlines the concepts of ‘autotelic’ and ‘exotelic’ experiences—the former being activities that are self-contained and intrinsically rewarding, while the latter carry an expectation of future benefit. This is illustrated through the example of Community Language teachers who were highly motivated to attend a series of drama workshops for professional development, but experienced a deepening of engagement through tapping into their intrinsic enjoyment of creativity. The indicators of flow are analysed at the group and individual levels, outlining how a consideration of both autotelic and exotelic aspects of engagement are relevant for Teaching Artists.