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While medical students often fear the avalanche of knowledge they are required to learn during training, it is learning to translate that knowledge into wisdom that is the greatest challenge of becoming a doctor. Part of that challenge is learning to tolerate ambiguity and uncertainty, a difficult feat for doctors who are taught to question anything that is not evidence based or peer reviewed. The medical humanities specialize in this ambiguity and uncertainty, which are hallmarks of actual clinical practice but rarely addressed in medical education. The humanities also force reflection and contemplation—skills that are crucial to thoughtful decision making and to personal wellness. Beyond that, the humanities add a dose of joy and beauty to a training process that is notoriously frugal in these departments. Well integrated, the humanities can be the key to transforming medical knowledge into clinical wisdom.