As we journey through life, people and events influence our direction and perception. The metaphor of life as a journey helps create a narrative of a person’s progression through the various life cycles. During our lives we create self narratives to explain how we see ourselves and how we fit into the world. As we proceed in the journey we change, as do our perspectives. Losing someone close to us has a profound effect on how we view and live our lives. The author was undertaking a Master’s in applied positive psychology when her father was diagnosed with terminal cancer. Her journey of growth and gradual change of perspective coincided with his death journey. Both journeys interacted and impacted greatly on each other. The strategies of positive psychology, especially those of gratitude and meaning helped the author to accompany and support her father on his final journey. The author reflects on the period through autoethnography, using her journal and daily social media posts as data. Using Thematic Analysis, five prominent themes were identified: death and grief, meaning and purpose, personal growth, coping mechanisms, and legacy. These themes are the focus of this case study. The interaction of these two journeys is examined, reflecting on what is important in living and in dying. In agreement with other existential positive psychologists, the author concludes that mortality awareness and meaning are both vital components of living life fully and reaching optimal potential.