There is a wealth of research (e.g. Nezlek, Newman, Todd & Thrash, 2017) highlighting the positive effects of keeping a gratitude diary on well-being. However, there is far less information available on the nature of these entries and whether they change over the lifespan. This paper presents a personal account of gratitude diary entries (5-7 generally entered weekly) spanning over half a decade. A content analysis was undertaken to see what the most common themes were; e.g. family, friends, health, career, finance, hobbies, nature/environment, travel, ‘existential moments’ that emerged. Moreover, by referring back to the author’s separate journal (generally kept daily), the frequency and type of gratitude items could be analysed with respect to significant (and often stressful) life events and major mid-life transitions (Levinson, 1977) involving career and country of residence. Whilst this account is necessarily introspective and idiographic, the author uses the findings to draw together broader issues in positive, developmental, and cognitive (e.g. autobiographical memory) psychology.