Failure is inevitable in the work we do. The systems we build, the processes we manage, and the teams we work in will all break at some point. But the fact that everything around us is fragile is not an invitation to accept things as they are. It is a calling to think deeply about the world around us, and to try and make the future a little less broken. By encouraging ourselves and our teams to talk about the potential challenges that lay in front of us, we give each other permission to think critically about the work we do and investigate our own biases. Through these discussions we can not only build more resilient systems but also reduce the downstream impacts of failure when they do inevitably happen. In this talk, I will use real-world examples as case studies through which we can develop strategies for turning weaknesses in our designs into strengths in our teams.