This chapter explores the ways that authors create self-representations purposefully, often through such playful and subversive interactions with digital technologies. It also explores how a cohort of university students used digital spaces creatively to construct self-representations. If the digital offers new forms of semiotic and discursive practices, the chapter investigates whether, and to what extent, students, and by implication teachers, could exploit potential of media. It also investigates themes underpinning contributions, and connected these to ideas emerging from the literature in relation to digital writing, pedagogies of disruption and to emerging teacher identities. Digital environments offer not only different time/space relationships but also a rich culture for play and identity performance. Elizabeth Losh argues that a conceptualization of "digital rhetoric" needs to move beyond any narrowly instrumental understandings and focus on design. To mobilize the possibilities of the rhetoric of twenty-first-century rhetorical practices, educators need to develop expanding understandings of the ways conventions can be pushed and challenged.