This chapter utilises the lens of “figured worlds” (Holland et al., 1998; Urrieta, 2007), to consider the ways in which educational leadership identity is framed by competing pressures. Through examining issues of leadership performance, disenfranchisement from educational belief systems and educational leaders’ ability to maintain critical consciousness, the chapter explores the uncomfortable compromises, the loss of stability, the shifts in identity and the rising levels of stress (Lewis, 2004) that educational leaders experience. This chapter challenges educators to examine their “taken-for-granted” practices and celebrate creativity and political thought in ways that enliven education and the experiences of learners.