The past twenty-five years have been dramatic changes in the transition to retirement. This article considers an overlooked set of social processes--informal age structuring--within the context of these changes. Data are drawn from a random sample of 319 adults from the Chicago area. For about half of the respondents, age was considered an irrelevant dimension for both men's and women's retirement. Those respondents who found age relevant cited deadlines that were clustered not only around the critical points at which researchers have observed regularity in retirement patterns, but they also included the lower junctures that are emerging as part of the shift toward earlier retirement. These deadlines most often marked the place of retirement relative to a larger set of work transitions, or they budgeted enough time to pursue developmental opportunities at the end of life. However, most respondents said there were no serious consequences for retiring late. Important patterns also emerged across the background characteristics of our respondents. These findings feed into several provocative debates that relate time and age to models of life-course flexibility or rigidity.