As educators, we are often socialized into a system that fears failure and seeks to avoid uncertainty. Yet, the world we live in and the one our students will inherit is full of complex, unscripted problems where the answers are not immediately known and the consequences matter. How might we best prepare students for such a future? What teaching and learning methodologies should be in our toolbox? What new knowledge, skills, and aptitudes must we acquire? In this address, we will explore the transformative power and potential of risky teaching— in its various forms and methodologies. Using examples from across the K-16 educational sector, we will consider how we can take more risks as teachers and, as a consequence, experience learning transformation.