Although the retirement transition is a complex and multifaceted process for older workers, much of the existing research only examines retirement from a financial or “encore career” perspective (i.e., work after retirement, which represents only one of several possible retirement lifestyles). As the baby boomer generation nears retirement age, a more comprehensive understanding of retirement is needed to improve successful planning for this transition. The career self-management model of social cognitive career theory was used as the conceptual base for the current study. Based on this model, five new social cognitive measures of retirement planning (self- efficacy, outcome expectations, supports, anxiety, and decidedness) and a revised goal measure were developed and administered to 525 older workers anticipating retirement in the near future. Data from the first 200 participants in the sample were subjected to exploratory factor analysis and other analyses to estimate their reliability and validity. Data from the remaining 325 participants were then subjected to confirmatory analysis and to path analyses to predict retirement planning anxiety, decidedness, and goals. The data provided good overall fit to the career self- management model, and support was found for most, though not all, predicted paths in the model. Implications of the findings for the career self-management model, as well as for future research and practice directions, are considered.