The aim of this article is to reconstruct two counter-intuitive Aristotelian theses--about contemplation as the culmination of the good life and about the impossibility of undoing bad upbringing--to bring them into line with current empirical research, as well as with the essentials of an overall Aristotelian approach to moral education. I start by rehearsing those essentials. I then illustrate the two theses and their counter-intuitive ramifications by dint of three life stories of imaginary persons. Subsequently, I offer a reconstruction of Aristotle's theses which, while going beyond the textual evidence, remains faithful to core elements of his moral and educational theory. I finally bring some considerations from the current literature on self-change to bear on this Aristotelian reconstruction, arguing that the effects of bad upbringing can be undone through contemplative activity. I also elicit some implications of the proposed argument for contemporary moral education and schooling.