“The shame and guilt over my inept handling of that first terrible diagnosis have stayed with me. When I make an awful discovery, the dread is still there, but I confront it. … I acknowledge that we both may have more questions than answers but promise that we’ll make a plan to get the answers.” Michelle Kittleson remembers a patient she saw more than 2 decades ago and what she learned about delivering bad news and providing comfort to patients who may be confused and scared. This essay was published in the Teaching and Learning Moments column in the October 2019 issue of Academic Medicine. Read the essay at academicmedicine.org.