How can doctors-in-training learn to have hard discussions with their patients? Will, a fourth-year medical student intending to become an internist, recounts two formative patient encounters he had during his third year. In the first, he learned from an attending physician and a man dying from cancer the challenges of determining when it’s time to end treatment. In the second, he realized a non-English speaking patient did not understand that she had lupus, and thus took the initiative to more effectively translate to her what the condition meant.