Our workforce continues to gray due to advances in medical science and new technology, which allows workers to remain in the workforce longer. Furthermore, we need our current workforce to remain motivated and work until an older age due to decreased birth rates and the smaller size of the post baby boomer cohorts. An in-depth examination of the motivation of our aging workforce is necessary to determine how we can increase motivation and keep older workers (those 55 and older) in the workforce longer, while remaining productive. In this study, three divisions of health (i.e., Major Illnesses, Functional Impairments, and Psychosomatic Illnesses) were related to three work goals (i.e., To-Work, At-Work, and To-Retire), combining aspects of the works of Feldman (1994), Shultz and Wang (2007), and Kanfer, Beier, and Ackerman (2012), using archival data extracted through the National Heath and Retirement Study (HRS). A two-step hierarchical regression was conducted with age, gender, wealth, education level, marital status, financial control, and ethnicity as covariates. Most hypotheses were partially supported, with Functional Impairments exhibiting a small effect on To-Work, At-Work, and To-Retire goals. Major Illnesses exhibited some unexpected relationships, however, as they were not positively related to To-Work and To-Retire goals. All health factors exhibited a negative relationship with a small effect on At-Work goals.