This paper takes up the question of risk by examining childhood memories of nuisance-making and punishment shared by 26 participants enrolled in teacher education and/or childhood studies programs. Our analysis surfaces a tension that, on the one hand, idealizes the child as innocent instigator of playful antics and, on the other, produces a child who is guilty of punishable acts. We read these memories as an invitation to theorize a middle ground of the teacher's role as one of introducing children to a world of limits, while also limiting the force of this very effort.