Susannah, Tarkington's second wife, urged him to "write about boys as they really are." She highlighted a British book on student life at Harrow, prompting Tarkington to remark, "no boy ever talked like the puppets in that story." Motivated to depict boys realistically, he found inspiration in his nephews and his own childhood experiences. This ultimately resulted in the creation of the Penrod stories.

In these narratives, Tarkington explored theories about childhood, proposing that as children grow, they replicate the evolution of human history, moving from savagery to civilization. In a 1925 article for the American Magazine called "What I Learned from Boys," he asserted that the ages between eight and fourteen are vital for a child's development. In the stories, Penrod is twelve years old and nearing the conclusion of this important stage. He represents a certain untamed nature, yet there are indications that this wildness is slowly being tamed.