This theoretical paper presents a person-environment fit framework that extends the Minnesota Theory of Work Adjustment to retirement transition and adjustment. The proposed Retirement Transition and Adjustment Framework (RTAF) also accommodates dynamic intra-individual and environment change over time, configural combinations of variables, and an ecological perspective to psychological-level decisions. The RTAF permits the collection of frequently sampled longitudinal person and environment data, allows for a detailed analysis of change and responsiveness, and can accommodate external influences from the family team, and social, economic and political policies. The paper concludes by using the RTAF to illustrate the types of psychological measurement and analysis opportunities likely to emerge in light of developments in the web, virtual reality, personal informatics and computing and information technology generally. (Contains 3 figures.)