Can professors, through their casual, random remarks to students, alter lives and transform identities? The answer, based on two exploratory studies described in this article, appears to be yes. Drawing from constructive-developmental ideas of student maturation and from features of chaos theory as applied to the complex dynamic system of student-faculty interactions, the author explores the mechanisms by which these moments exert their transformative power. During college, as they move away from parental influence to establish their own inner authority, students are particularly sensitive to the comments of professors. If brief, inadvertent remarks can change lives, then faculty should be intentionally mindful of their potential impact on the development of college students. Although planning for serendipity may seem like an oxymoron, the article explores ways for faculty to stimulate these moments in students, suggests avenues for future investigations of the phenomenon, and speculates about how student and faculty assessment practices may need to change. (Contains 2 tables.)