Much has been written about the qualities of a good leader and teacher, especially if good is loosely employed as a synonym for competent or successful (Darling-Hammond 1996; Zhao 2010). Of course, an educator’s being good or ethical overlaps with being competent, but the two interests, even when intersecting, are distinguishable (Biesta 2015). Our interest largely focuses on traits (e.g., attitudes, dispositions, habits) and behaviors (e.g., acts, conduct, endeavors) that help describe a person as good regardless of whether they are a cashier, principal, parent, politician, or social worker. Obviously, the roles one accepts – familial, civic, career, government – affect some, if not many, manifestations of one’s character. Considering the complexities of an individual’s personality, life, and culture, Dewey thought that behavioral expressions of qualities are multifaceted, being variable yet stable, personal yet situational, organismic yet contextual, and predictable yet unforeseen. For him, these factors and more influence how a person comes to be described as a good or ethical educator.