Retirement is rarely conceptualised in terms of learning and development. However, as the end of professional activity approaches, many people begin to reflect deeply on the past, present, and future of their lives. This potentially profound reflection involves a complex process of learning and development to which research has paid too little attention. This article places the voice of a retiree at the centre of the study and provides a nuanced understanding of retirement, sensitive to the changes and difficulties of narrative sense-making activity in this transition, with all its ambiguities and complexities. The article analyses the 24-year diary of a man who goes through retirement, exploring the narrative sense-making dynamics by which this diarist interprets his retirement: initially it is mentioned with a combination of desire, idealisation, fear, and insecurity; then it is experienced as a deep personal crisis with depression; and afterward it is reinterpreted in a nuanced, positive, and constructive way. The analysis reveals the intertwining of cultural and personal dimensions in narrative sense-making. Sense-making around retirement is not passive or merely descriptive of the event, but instead is an integral part of what the process of retirement itself can become.