Simply Reader's Wonderland

His pedagogy involves the students taking responsibility for their own learning, especially in his first school, McKee Vocational and Technical High School, in New York. On the first day he nearly gets fired for eating a sandwich, and the second day he nearly gets fired for joking that in Ireland, people go out with sheep after a student asks them if Irish people date. Much of his early teaching involves telling anecdotes about his childhood in Ireland, which were covered in his earlier books Angela's Ashes and 'Tis.

He then taught English as a Second Language and took some African American students to a production of Hamlet. He talks about when he was training as a teacher and didn't know anything about George Santayana, but was able to give a well-prepared lesson on the war poets Wilfred Owen and Siegfried Sassoon. Other highlights include his connection between how a pen works and how a sentence works (in explaining subjects and grammar, an area which he struggled with himself) and his use of realia like the students' excuse notes and cookbooks.

He taught from the time he was twenty-seven and continued for thirty years. He spent most of his teaching career at Stuyvesant High School, where he taught English and Creative Writing.

He earned a Teacher of the Year award in 1976. During the time of the book he went to Trinity College to try to take his doctorate, but he ended up leaving his first wife because of the strain.