Education, Failure, and Growth Theme Analysis

Although Old School takes place at an elite prep school, the narrator rarely describes his lessons in the classroom. Instead, the story focuses on the importance of practical life experience and failure as a means of education. In particular, Wolff demonstrates how practical experiences make great lessons for the narrator and for the dean of the school, Dean Makepeace—both of whom leave the school prematurely due to personal failures. Yet this leads to great personal growth for both men, as they learn about themselves and more fully understand their paths in life. Their trajectories suggest that lived experiences—particularly failures—often provide more valuable lessons than formal education does.  

The advice that visiting writers give to the students introduces the idea that failure and practical experience are important kinds of education. When poet Robert Frost visits the school, he has a one-on-one conversation with the narrator’s friend, George Kellogg. Kellogg relays to the narrator that Frost’s advice is to go to a place like Kamchatka. The narrator wonders, “What was it about Kamchatka, that a young writer should forsake his schooling to go there?” The narrator decides to read about Kamchatka and discovers that it is a remote peninsula in the far east of Russia. He comes to the conclusion that Frost means they should experience “Solitude, darkness, and hardship” to become great writers. Frost’s advice emphasizes practical experience as an important means of education. Later, when Ernest Hemingway is interviewed for the school paper, he suggests the same thing. Commenting on a story the narrator submits (though it is later revealed that he plagiarized this story), Hemingway explains, “The kid knows what he's writing about and that’s good, now he should go out and know some other things to write about.” Like Frost, Hemingway stresses going out into the world and gaining firsthand experience as the best education for a writer.

The narrator gains this practical experience when he is expelled for plagiarism, and his subsequent success as a writer was born out of this failure. When the narrator plagiarizes a story for the school’s literary competition during his senior year, the school expels him, and Columbia University rescinds his acceptance for the following year. He is devastated, feeling that his time at the school and the success he would have achieved at Columbia have been reduced to a “paling dream.” The narrator leaves for New York and, unable to find a job as a writer or copyeditor, works a series of odd jobs and then enlists in the army. His failure in school puts him on a different path—one that gives him a variety of experiences that he wouldn’t have had otherwise. The narrator then underscores how only through this “floundering” does he “learn[] to be alone in a room, learn[] to throw stuff out, learn[] to keep gnawing the same bone until it cracked.” While he explains that “the life that produces writing can’t be written about,” he does imply that only through failure and a more meandering path in life is he able to grow as a person. The narrator’s success as a writer is then affirmed when a former teacher, Mr. Ramsey, invites him back to the school as a visiting writer. The narrator worries he is not worthy of the honor and does not belong at a table with writers like Hemingway, Frost, and Ayn Rand. But Mr. Ramsay assures the narrator that he does belong at the table. The narrator’s failure has enabled him to become a great writer—so great that he is welcomed back in honor to a place that he left in disgrace.

The dean of the school, Dean Makepeace, follows a similar journey: only through resigning his position at the school does he grow and learn about himself. The dean resigns from the school the day the narrator is expelled because he, too, broke the Honor Code: he lied for years about knowing Ernest Hemingway. Even though he is sad to leave, he knows it is the right thing to do, because his lies are a betrayal of his moral character. After resigning, Dean Makepeace takes trips and spends a lot of time alone, to the point where he “hardly [feels] himself to be alive.” In this time away from the school, he realizes how much he misses his post—the respect of the boys, the literary conversation, and the feeling of having a purpose. Understanding how much he needs the school, Dean Makepeace humbly asks the headmaster to reinstate him in his old position, and he’s welcomed back with open arms. Lake the narrator, it takes failure for the dean to learn and grow as a person, and then to regain success at the school.

The narrator and Dean Makepeace’s journeys are tied in one additional way: when the narrator contemplates returning to the school, he notes that faculty members would “welcome the prodigal home.” When the dean is greeted by the headmaster, he recalls the words “His father, when he saw him coming, ran to meet him.” Both are references to the story of the Prodigal Son, a New Testament parable in which a son asks for his inheritance before the death of his father, leaves home, and squanders it. But when the son returns and acknowledges his failures, his father warmly greets him. The story emphasizes that failure should be viewed as an opportunity for learning and growth, and the dean’s and the narrator’s trajectories both illustrate that idea.