Abstract Objective. This study is the first part of a longitudinal investigation of the retirement process. This stage of the inquiry concerned how older persons anticipate their retirement. Method. Thirty-two workers were randomly selected from all workers age 63 years in a suburb of Stockholm. They participated in semistructured interviews about their work and their expectations for retirement. Results. The participants’ narratives illustrated the complex work of interpreting the past and expected meaning in one’s occupational life. The narratives, which anticipated widely different future trajectories, revealed many of the challenges and dilemmas of anticipating retirement and the close association of work experience to expectations for retirement. In particular, the narratives highlighted the participants’ concerns about maintaining the quality of experience in activity. The findings also demonstrate the process by which persons anticipate and make choices about life change. Conclusions. People anticipate retirement through volitional narratives in which they link together past, present, and future. Understanding this volitional process of interpreting, anticipating, and making choices is important to understanding how people adapt to life changes.