Gary Schmidt's main message in The Wednesday Wars is to show that personal growth develops as a consequence of defeat, just as Holling grew from defeat.
Schmidt's message is first revealed when Holling reads The Tempest in November, which became one of Holling's favorite plays and led to many moments of personal growth. Mrs. Baker reveals the message when she explains to Holling that Shakespeare uses Caliban to show that a part of human nature "uses defeat to grow." At first, Holling objects to her assertion, saying, "Defeat doesn't help you grow. ... It's just defeat." Yet, the more Holling experiences his own defeats and rises above them, the more he sees he was wrong.
One defeat of Holling's that he considers to be his most humiliating is having his picture taken playing Ariel in The Tempest, dressed in yellow tights decorated with white feathers on the backside. Holling's photograph is proudly displayed on the cover page of the town's newspaper on New Year's Day. Worse yet, Doug Swieteck's brother decides to plaster clippings of the picture all over the town's schools, making Holling feel like a humiliated, defeated failure.
Though Holling feels defeated, he finds a way to rise above his defeat. First, he tries to revenge himself on Doug Swieteck's brother by pelting him with an icy snowball. The taste of revenge, however, doesn't last long, because Holling is soon threatened with being pelted with snowballs by not just Doug Swieteck's brother but all of his juvenile delinquent friends as well. Luckily, at the exact moment Holling is about to be pelted, his sister is also about to get hit by a school bus sliding out of control on the icy road. Holling flies to her rescue and pushes her out of the way but is hit in the backside by the bus's rear bumper. Holling's rescue mission is also caught on film and published on the front page of the town's newspaper. Holling arrives at school the next day to discover someone had replaced the humiliating photo that plastered the schools with his new heroic photo. Hence, based on this story, we can see that Holling successfully used his love for his sister and his integrity to overcome his defeat and grew as a consequence of the experience. Throughout the book, Holling overcomes many other defeats as well.