This article is a revised and abbreviated version of a session that the authors presented at the 25th annual Lilly Conference on College Teaching, November 19, 2005, in Oxford, Ohio. It arose from their joint conviction that while teaching is the greatest job in the world, teachers do not need to stay in it until death do them part. Beidler and Van Vliet talked about some of the things they themselves had faced recently: how to plan for the inevitable, how they came to know it was time to cash in their academic chips, how they got their heads right for the great move into the unknown, what the unknown is really like, why teaching and retirement are not all that different from one another, and why they feel that teachers owe it to their students and their colleagues to step aside gracefully. They took turns doing the talking, and there was a lively discussion afterward. At the end of this article is an edited version of parts of that discussion.