This workshop will explore ideas and methods to foster a positive culture around making mistakes in the middle school math classroom. Through a series of hands-on activities, participants will model strategies that foster a learning environment where mistakes are de-stigmatized and embraced. We will use an app-based game as a tool to support student metacognition around meaningful, real-world math problems that connect to specific topics, such as Area, Surface Area and Volume of Two- and Three-dimensional Objects (CCLS 7.G.6), and Understanding Ratio Concepts and Using Ratio Reasoning to Solve Problems (CCLS 6.RP.3). We will also look at common student misconceptions for these content areas from both a teacher and student perspective and discuss opportunities for leveraging an understanding of these misconceptions to enhance classroom pedagogy. Open and applicable to math teachers of varied levels.