In this conversation, Gillian Stovel Rivers and Greg Barnsdale explore the critical importance of mortality planning, discussing the universal challenges surrounding death and incapacity. They highlight the alarming statistic that only 15% of Canadians have an estate plan, emphasizing the need for open conversations about end-of-life wishes to reduce stress and strengthen family relationships. The discussion delves into the financial implications of poor planning, the role of communication in legacy planning, and the potential of online will creation. Cultural perspectives on death planning are examined, along with the necessity of executor education to ensure effective estate management. Ultimately, the conversation underscores that handling mortality planning well is a profound act of love for one’s family.