This paper examines diagnostic error from an educational perspective. Rather than addressing the question of how educators in the health professions can help learners avoid error, however, the literature reviewed leads to the conclusion that educators should be working to induce error in learners, leading them to short term pain for long term gain. A variety of literatures are reviewed that suggest errors in performance are necessary pre-conditions for learning to occur such that an aversion to errors, while more comforting to the learner, is counter-productive. Similarly, research is reviewed that suggests strategies aimed at avoiding heuristic-driven diagnostic errors may successfully reduce those types of errors, but may do so at the expense of inducing errors of comprehensiveness. Taken together, the variety of studies contained suggest that diagnostic errors are often beneficial and that we as an educational community should strive to determine how to harness their pedagogical and diagnostic benefits rather than simply trying to eliminate mistakes entirely.