This deliberately playful article explores the work of cognitive psychologist Lev Vygotsky, in particular the anecdote he shares in his 1933 essay on play and the development of the child, in which two sisters play at being sisters. Vygotsky uses the anecdote to reflect on the role of rules—and their absence—in playful becoming and conditioned social behaviour. Here, I revisit Vygotsky’s anecdote to re-cast it into the research and creative practice context in the contemporary university setting. How might we think about the play of rules and their absence in relation to doing and/or becoming research and creative practice academics? In this article I complement the Vygotsky anecodote with a consideration of the Glasgow series of paintings of two sisters by British artist Joan Eardley. I unearth what we know about Eardley’s creative process in the production of her series of portraits of the Sampson children during the 1940s, and explore the ways in which that process or practice can be said to reveal something about the importance of immersive repetition, playful re-working, and the constant casting off (and on again) of rules. The article also draws on some recent qualitative research by the author on the role of play in contemporary Australian research practice.