With America's population aging and America's late-life workforce eschewing the traditional retirement path, the stability of retirement pathways must be reanalyzed to better reflect this heterogenous demographic. Through generational analysis, we see that there is only a slight change in employment stability for generations of those 50-74. However, we see vast differences in employment stability by spousal status. Employment of a spouse and being coupled versus living alone result in differing opportunities to switch careers or retire. This research indicates that a dyadic focus in retirement plans and employment stability is crucial for analyzing the older generations' life trajectories.