Retirement has traditionally been conceptualized as a point‐in‐time decision to physically and psychologically withdraw from the workforce on reaching a certain age. However, the expectations of older workers demonstrate a new retirement paradigm, with many more retirement trajectories. The purpose of this study was to examine actual career decisions being made by older workers and to understand sociodemographic factors that might differentiate their career trajectories. Data from the Health and Retirement Study (Juster & Suzman, ) were analyzed using multinomial logistic regression to compare 4 retirement trajectories (i.e., no retirement, full retirement, bridge employment, and encore career). Gender, age, education, marital status, health, and wealth differentially predicted the odds of pursuing each of the 4 retirement decisions. Career practitioners may use these results to help baby boomers make retirement decisions and provide them with appropriate education, guidance, and resources. Additional research is needed to examine other factors salient to each of the retirement trajectories.