Throughout the book, the author alternates between the academic perspective of medical historian and ethicist and the personally-invested view of a devoted doctor and son. Gawande presents the experiences of his patients and his father as they face terminal illness and make end-of-life decisions. He recounts both moments when he was unable to have a true conversation about death with a patient, as with his patient Lazaroff. He also recounts more successful moments, such as those shared with Jewel Douglass, when he practiced medicine in the guidance style he believes best serves patients who are up against hard choices. 

Gawande’s wife’s grandmother serves as an example of how nursing homes can adversely impact the mental health of the elderly. When her physical health begins slipping, it becomes clear that she needs assistance. When moved into a nursing home, however, she becomes despondent. After an active and independent life, Hobson responds poorly to nursing staff telling her when to wake, what to eat, when to bathe, and when to go to bed. The author insinuates that there could’ve been a more meaningful way for her to pass rather than dying alone with chest pains, coughing up blood.