This paper explores possible tactics for academics working within a context of regulation and constraint. One tactic we suggest is moving outside of a creativity/conformity binary. Rather than understanding creativity and conformity as separate, where one is understood as excluding the other, we discuss the potential of examining the relationships between them. We use the theme of ‘structure and play’ to illustrate our argument. In the first part of the paper using various examples from art and design, fields generally associated with creativity, we explore the interrelatedness of creativity and conformity. For example, how might design styles, which are generally understood as creative outcomes, constrain creativity and lead to conformity within the design field? Is fashion producing creativity or conformity? Conversely, the ways conformity provides the conditions for creativity are also examined. For example, the conformity imposed by the State on artists within the communist block and how this contributed to a thriving underground arts movement which challenged conformity and State regulation. Continuing the theme of ‘structure and play’ we provide a story from an Australian university which offers insight into the ongoing renegotiation of power in the academy. This account illustrates the ways programmatic government within the university, with the aim of regulating conduct, contributed to unanticipated outcomes. We propose that a relational view of power is useful for academics operating in the current higher education context as it brings into view sites where power might begin to be renegotiated