Metacognition supports students in successfully working through struggle by equipping them with the tools to maintain an awareness of what they are doing and to change directions when needed to overcome obstacles. Thus, it is of little surprise that effective problem solvers spend a significant amount of time analyzing tasks relative to the amount of time they actually spend solving those problems (Schoenfeld, 1989). This article examines how teachers can create opportunities for students to solve challenging tasks and problems which is not only a critical component of mathematics education curricula (NCTM, 2014), but it also allows students to experience the joy, beauty, and wonder of mathematics. These learning experiences equips students with the tools necessary to be successful by supporting them in making sense of tasks, analyzing and evaluating potential solution pathways, and engaging in continuous reflection during and after solving the problem.