All this he called “doing his duty by their parents;” and he never inflicted a chastisement without following it by the assurance, so consolatory to the smarting urchin, that “he would remember it and thank him for it the longest day he had to live.”

One of the narrator’s first descriptions of Ichabod is how he handles discipline in his classroom, showing that Ichabod believes corporal punishment teaches children to behave and turns them into respectful adults. While this was not an uncommon belief at the time, his choice to punish the stronger boys while sparing the weaker boys shows he is not as fair as he believes himself to be. It also shows Ichabod’s self-righteous streak and highlights his lack of self-awareness about his own actions.

The schoolmaster is generally a man of some importance in the female circle of a rural neighborhood, being considered a kind of idle gentlemanlike personage, of vastly superior taste and accomplishments to the rough country swains, and, indeed, inferior in learning only to the parson.

In the beginning of the story, the narrator humorously pokes fun at Ichabod’s high opinion of himself, which is often at odds with reality. He views himself as an educated gentleman who is superior to the less-educated farming men of Sleepy Hollow. His lack of self-awareness leads him to believe he is something of a ladies' man in spite of the fact that his small salary as a schoolteacher leaves him unable to support himself, much less a wife and family.