This research examines the alternative mechanisms by which occupations influence the nature and timing of older men’s labor force withdrawal. We specifically assess the extent to which occupational factors operate directly and indirectly on exiting events and whether occupations constrain traditional determinants of labor force participation. Based on a discrete-time hazard modeling approach, the results substantiate that the occupational task activities—substantive complexity and physical demands— are key elements of the work environment that are evaluated against nonwork alternatives. In the case of retirement, these aspects of occupational attractiveness function as a dominant and direct force in retirement decision making. With regard to disability, the occupational attribute of substantive complexity operates as an indirect advantage (through higher wages) by reducing the risk of disability. Indicators of career continuity also influence retirement among older workers. Finally, the results suggest that financial characteristics and health problems are central to the distribution of older workers across the alternative destination statuses of retirement, disability, and death.