This article presents the results from a longitudinal study of retirement. Data were collected through interviews with 12 Swedish participants over a 7-year period, beginning when they were still working and continuing through their early years of retirement. The findings show that the participants’ narrative anticipations of retirement interacted with the events of ongoing life. Sometimes these events influenced the outcomes of the retirement process unpredictably. Consequently, retirement was often full of surprises and temporary periods of turbulence. Although some participants managed a transition into a satisfying pattern of retirement, others found it an ongoing process of frustration and dissatisfaction. Evidence from this longitudinal study indicates that a special type of occupation—engaging occupation with six constituents—was an important determinant of retirement satisfaction. This key finding is discussed with regard to its implications for theory development as well as its practical implications related to the importance of differentiating occupations and attending to the interaction between internal motivation and external expectations in the occupational pattern.