Population aging and attendant pressures on public budgets have spurred considerable interest in understanding factors that influence retirement timing. A range of sociodemographic and economic characteristics have been shown to predict both earlier and later retirement. Less is known about the role of occupations and their characteristics on the work choices of older workers. Knowing more about the occupations that workers seem to stay in longer or leave earlier may point the way to policy interventions that are beneficial to both individuals and system finances. This project uses detailed occupational categories and work characteristics in the Health and Retirement Study (HRS) linked to information in the Occupational Information Network (O*NET) to examine compositional changes in occupations held by older workers over time; to provide some basic and interesting information about relationships between occupations and their characteristics and retirement expectations and outcomes; and to shed some light on which occupations and associated characteristics might encourage or discourage longer working lives. There are large percentage changes (increases in decreases) in the percentage of older workers in occupations over time. Considering detailed as opposed to aggregated occupational categories yields interesting additional information. Jobs that HRS respondents say entail less physical effort, less stress, and jobs that have not increased in difficulty in recent decades, and those in which people can reduce hours if desired, are associated with longer work. While the traditional blue collar-retire earlier and white collar-work longer associations emerge, we find interesting exceptions that suggest fruitful directions for future research.