We experience judgment in everyday life: the process and the outcome, making and receiving. In this piece, I turn to John Dewey’s notions on how judgments are situational, interpretive, (con)temporary, active, and relational. Contrary to everyday connotations of the word judgment, Dewey reminds us that judgment is more contingent than propositional. The aim of this piece is to re-consider our understanding of judgment in everyday educational work. Crafted from a range of sources, anecdotes are alternated with statements about judgment in the work of school principals and teachers, one to illustrate the other. The form chosen for this project echoes that of Ron Pelias’s 1994 piece on performance in everyday discourse.