Death has a terrible user experience. We will all face this inescapable occurrence, yet no one knows how to talk about death, how to prepare for it, or what to do when it suddenly rips it’s way into your life. Using first hand accounts which were obtained through the recent loss of my Father, I will discuss how poorly designed experiences begin right at the moment that one is faced with death—and how each of those moments is an opportunity for human centered design to comfort and support rather than to frustrate. Whether designing for others or for ourselves, we have a responsibility to design solutions that focus on empathy, compassion and streamlined approaches for this inevitable human experience.