This paper provides an evaluation of the Heart of Living and Dying (HLD) Initiative. This initiative is a group process that attempts to bring Advance Care Planning (ACP) into the public domain. It encourages participants to consider what matters to them in their living along with their hopes, preferences, and wishes for their final years and end-of-life care. An inductive, interpretive, and naturalistic approach allowed the researcher to study these phenomena in their natural setting i.e., the community. This qualitative study used 5 focus groups with 17 people and employed thematic data analysis to identify key themes. All participants in the HLD speak from a personal perspective irrespective of any professional background. It transpired that 16 respondents worked in health and social care, which subsequently became noteworthy in the findings. Three key themes were identified: (a) feeling emotionally safe enough to have such sensitive conversations is vital; (b) participating in the HLD process increases the confidence of those participants who worked in health and social care, to undertake ACP conversations and (c) planning ahead is a complex, staged process rather than a single record-making event. The Covid-19 pandemic crisis reinforced the need to upstream ACP initiatives such as the HLD, as the norm for everyone, since all of us will one day die. It is recommended that the HLD be incorporated within ACP training given that the experiential nature of it and the use of groups was reported to build confidence in facilitating ACP conversations. A virtual HLD process needs to be developed to adapt to restrictions on gatherings due to Covid 19.