We all fail. We also like to look good and avoid looking bad. So, even though we know that taking risks and trying new approaches are important for enhancing our teaching and students’ learning (Strean, 2017), we rarely talk about our failures. Our claim in this paper is that our insecurities create a substantial barrier to improving and enriching our teaching practices. If we do not find time to take big risks, and then to explore and critically reflect on failures that result sometimes from those risks, we lose out on the chance to become better teachers; more fundamentally, we deprive our students of the chance to have extraordinary opportunities to learn.