Children’s intellectual risk-taking behaviors influence their motivation, wellbeing, and achievement in the classroom. But how do pupils perceive their own actions in intellectual risk contexts, and what is their perception of preferred difficulty and the consequential effects of intellectual risk taking? This article presents children’s perspectives on intellectual risk as transient, personalised insights which may help educators and researchers to access the multivariant realities which always exist in education, and as effective tools to explore the cognitive and lived experiences of the children in our classrooms. Through detailed consideration of recent literature, and the employment of Clifford’s (1991) School Failure Tolerance Scale, I present what could be a possible framework for researching pupils’ perspectives on intellectual risk taking, and consider the implications of such research in regards to my own practice.