Retirement can be a time of pleasant anticipation--sleeping beyond sunrise, trying out new hobbies, reconnecting with family and taking long-planned trips. But superintendents face unique challenges as they move from frenzied morning-to-evening work schedules to relatively empty days. Many find the decision to retire bound up with the anxiety of leaving a well-established environment with a lofty set of expectations for the unknown world of independence. This article contains personal accounts on retirement from former superintendents.