This article offers an introspective meditation on what William James described as the “fallible utility” of introspection, promoted here especially for countering experiences of shame, self-loathing, and melancholia—what Adam Phillips calls states of “total conviction”—in boys and men. The article draws on narratives from James’s and the author’s own youthful struggles and from James’s “On a Certain Blindness in Human Beings,” an essay he believed best captured “the perception on which [his] whole individualistic philosophy is based.” It urges boys and men to attempt, against considerable odds, to practice a more generous self-acceptance, particularly of forbidden homoerotic interests, as their path to greater tolerance of idiosyncratic others.