During the early 1960s, Norbert Elias led a research project on the adjustment of young workers to work situations and adult roles. The data from this project, which consisted of 851 interviews with young people, were recently rediscovered and the participants, now approaching retirement, were re-interviewed as part of a restudy. In this paper we argue, that, in the context of the dramatic changes to the transition to retirement that have taken place in the United Kingdom, it is possible to use Elias's unpublished work on the transition to work as a theoretical framework for understanding of the transition from work and to retirement. In particular, we focus on the themes of fantasy and reality in the perception of retirement; changing interdependencies in the transition to retirement and the extent and impact of retirement preparation on the perception of the change in status from full-time worker to retiree. We conclude by suggesting that the implied advantages of being the ‘baby-boomer’ generation are far from the reality, with the experiences of this group being similar to those who have gone before and face an adjustment to retirement marked by uncertainty and anxiety.