This researcher explored the experience of anticipatory grief among individuals living with cancer, their primary caregivers, and their families. Whereas conventional research into the experience of anticipatory grief tends to address its psychological, social, and physical responses, this dissertation includes exploration of the spiritual aspects of grief, dying, and death. Three primary questions were addressed: What is the experience of anticipatory grief as it relates to one’s illness? What is the experience of living with cancer? What is the experience of participating in Hospice Calgary’s Living with Cancer day program? An exploration of these questions utilizing heuristic research methods enabled the researcher to gain insight into the challenges, fears, and hopes of individuals and families affected by impending loss. Coresearchers reported that the initial diagnosis of palliative cancer triggers the experience of anticipatory grief, not just in the individuals receiving the diagnosis, but for their primary caregivers and families as well. The anticipatory grief trajectory, as responses to a series of multidimensional and multileveled changes and losses, is represented with a roller coaster metaphor. In the beginning it appears sharply spiked with shock, fear, anxiety, sadness, depression, feelings of overwhelm, emotional ups and downs, and feelings of helplessness by all coresearchers. Yet once the shock of the initial diagnosis was absorbed, all individuals began to move out of denial, adapted, and developed coping strategies. All individuals began to manage their illness and live with cancer. The most reported coping strategy was emotional and social support. When approached from a transpersonal perspective that embraces death as a transition rather than a final exit, the opportunity to experience conscious living and conscious dying begins to emerge. When death is accepted, anticipated, and prepared for, the fear and suffering experienced by those who are dying and their loved ones may be significantly alleviated.