Self-Identity
One of the multiple-chapter story arcs in the narrative is that of a new student named Benjamin Nushmutt. On his very first day of class, however, Mrs. Jewls mistakenly introduces him as a student named Mark Miller. Benjamin feels intimidated enough to have to stand in front of a classroom full of kids he does not know, and the mistaken name only makes this anxiety all the worse. Throughout the book, Benjamin will try at various times and under differing circumstances to correct this mistake, but something always seems to go wrong. Eventually, Benjamin meets a girl named Allison and engages in a conversation in which he is referred to as being both Benjamin and Mark. The theme which the story of Benjamin/Mark pursues is the way in which peer pressure can imprint a false self-identity upon one's actual identity.
Critique of Rote Memory Education
The book has three different Chapter Nineteens. This repetitive numbering of chapters which actually are not identical in content commences the thematic critique of the purposeless futility of teaching through rote memorizing of facts. The very same Allison who is part of Benjamin's story arc has her own story arc in which she accidentally discovers she has become a student in Miss Zarves' class on the "non-existent" nineteenth floor. Miss Zarves' frustration with being a "non-existent" entity teaching a "non-existent" class on a "non-existent" story of the building—due to a numbering mistake during construction—is manifested by assigning busy work rather than actually teaching. The critique of this style of teaching is most effectively situated in a student named Virginia. Virginia reveals to Allison that she has been memorizing the dictionary one page at a time in Miss Zarves' class for thirty-two years and still hasn't been promoted to the next grade.
Celebrating Individuality
Wayside School has thirty floors with each floor being a separate classroom. The focus of most of the book, however, is on Mrs. Jewl's class at the top of the building. The book has thirty chapters that relate the stories of a multitude of characters. While these characters interact with each other, many of them are the focus of their own specific little subplot. Thus, the book celebrates individuality within the context of social cohesion. The story of Miss Zarves being told across three separate chapters numbered Chapter Nineteen is juxtaposed with chapters 20, 21, and 22 all taking place within the same single chapter division and telling the story of three students named Eric. This chapter situates the principle of Wayside as essentially being unable to detect the difference between the three Erics who, notably, are not identical in appearance. This celebration of individuality is a theme that connects both with the critique of non-individualized teaching and the impact of other people on developing one's self-identity.