Salutary retirement policy depends on a clear understanding of factors in the workplace that contribute to work ability at older ages. Research in occupational health typically uses either self-reported or objective ratings of the work environment to assess workplace determinants of health and work ability. This study assessed whether individual characteristics and work-related demands were differentially associated with (1) self-reported ratings of job resources from older workers in the Health and Retirement Study, and (2) corresponding objective ratings of job resources from the Occupational Information Network (O*NET). Results from regression and relative weights analyses showed that self-reported ratings were associated with self-reported job demands and personal resources, whereas corresponding O*NET ratings were associated with differences in gender, race, or socioeconomic standing. As a result, subjective ratings may not capture important aspects of aging workers’ sociodemographic background that influence work ability, occupational sorting, opportunities for advancement, and ultimately the job resources available to them. Future studies should consider including both subjective and objective measures to capture individual and societal level processes that drive the relationship between work, health, and aging.