Organisational psychologists Beehr and Bennett (2007) explain that ‘as the babyboomer population ages, the number of retirees and the proportion of the society they represent will almost certainly increase to levels never before seen. Thus it is now more important than ever to understand retirement’ (p. 277). Internationally the baby boomer retirement bulge is creating significant succession and retention challenges for workforces. In the educational community the large number of impending principal retirements (due to the baby boomer effect) is presenting educational jurisdictions with similar workforce challenges: a shortage of principals and a loss of corporate knowledge. Given this developing scenario it is timely to ask: can educational jurisdictions afford to lose large numbers of late-career baby boomer principals? Are these late-career principals (as older workers) a dispensable cohort which has reached its ‘use-by-date’ or are late-career principals a valuable resource for extending the leadership capacity available for school systems? Are these experienced principals easily (and effectively) replaceable or will their departure expose inexperienced aspirants to the increasing challenges of current principalship? Before exploring these issues this article first seeks to investigate the views of late-career principals themselves. Do late-career baby boomer principals wish to retire in the traditional model (moving from full-time work to full-time leisure as soon as possible) or do these principals represent a retirement dynamic which is more interested in the concepts of stayingon and/or refocusing?