You might enjoy Alan Schoenfeld's book Mathematical Problem Solving, which tries to analyze the way that novice problem solvers make a hash of relatively easy '

You might enjoy Alan Schoenfeld's book Mathematical Problem Solving, which tries to analyze the way that novice problem solvers make a hash of relatively easy 'non-standard' problems, while expert problem solvers prevail, even when the novices have more immediate and direct experience with the required background knowledge for the problem. The biggest difference is that the experts do a lot more planning, introspection, and strategic adjustment along the way, while the novices immediately start down one wrong track and get stuck in the weeds, forgetting what they were trying to do or why.