The script for later life is being re-written, in part due to increased longevity, improved health, shifts in the economy, and changes to pension systems. Thus, we solicited a series of papers from members of the Sloan Research Network on Aging & Work that examine changes in the meaning and experience of work in later life, with implications for future research, employers, and policy makers. The articles selected for this special issue provide new insights about two aspects of the realities of aging and work today: (a) assets that older adults can bring to their work (Zacher, Hacker, and Frese; Scheibe, Spieler, and Kuba); and (b) challenges that can affect the successful engagement of older workers (Curtis and McMullin; Fisher, Ryan, Sonnega, and Naude; Moen, Kojola, Kelly, and Karasakaya). The findings provide new insights, and they importantly echo a message urging researchers to reach beyond the forecasts and analyses of trends associated with the phenomenon of working longer. The articles suggest that scholarship which examines patterns of work and retirement transitions is ready to explore new questions and carefully consider the nuances of job fit over the life course. It is no longer sufficient to design studies, policies, and practices that focus only on whether older adults can successfully get and retain jobs.