Emerging research points to the importance of developing the capacities of teachers to help their students to be creative risk takers and to learn from productive failure. Facilitating this creative risk taking in learners has been shown to require expertise and a degree of risk taking on the part of both teachers and educational leaders. This article explores perspectives about leadership for creativity and risk taking, using Kurt Lewin's theory of change, especially his idea of 'unfreezing'. It is based on a case study of a school principal and six year 8 teachers at a private school in Melbourne, Australia. Using qualitative interview data, the principal's perspective about change is explored and compared to how teacher participants enacted change in their practice as reported in a focus group. Examples from classrooms are reported from the perspective of teachers. The findings suggest that enacting creative risk and productive failure as pedagogical principles is a complex area of change, embedded with tensions between the realization and idealization of a leadership vision and critically involves the disposition of students. Meaningful enactment requires support from leadership and a willingness from teachers to be open to such ideas in the multidimensional space of classrooms.