End-of-life conversations are a difficult part of medicine. The COVID-19 pandemic has made them simultaneously more necessary and more difficult. Encouraging patients to have these conversations with their own providers and loved ones can help ensure, when the unfortunate time comes, their end-of-life wishes are carried out. This honors the patient and limits burden on others. Here, I reflect on how my personal experience as both a grieving grandson and as a resident physician has emphasized the importance of end-of-life conversations.