What is an example of a lesson Holling learns in Gary Schmidt's The Wednesday Wars?

Holling learns multiple lessons throughout Gary Schmidt's The Wednesday Wars. The more Holling learns about Shakespeare, the more Holling is able to apply Shakespeare's lessons to his own life. One of the early lessons Holling learns concerns Shakespeare's characterization of Shylock in The Merchant of Venice. Holling realizes that Shylock isn't actually a true villain; he's a product of his environment. Holling is then later able to apply the lesson to better understand his own father.

The very first play Holling reads with Mrs. Baker is The Merchant of Venice. When Mrs. Baker asks Holling about his thoughts on Shylock, Holling notes that Shylock "isn't really a villain" in the proper sense because Shylock is "[s]omeone who wants to become who he's supposed to be," but he is prevented by society around him ("November"). Members of society have "decided he had to be a certain way, and he was trapped. He couldn't be anything except for what he was" ("November").

Later, in February, he begins reading Romeo and Juliet with Mrs. Baker. During this same month, he asks Meryl Lee Kowalski out on a Valentine's Day date. Meryl Lee's father is the owner of Kowalski and Associates, the architecture firm Holling's own father is competing against for the contract to design the new junior high school. After their date, while waiting for Mr. Kowalski to pick them up, Holling and Meryl Lee enter a friendly, relaxed conversation about the amount of work their fathers are putting into their designs for the school. Holling feels so comfortable with Meryl Lee that he draws her a picture of his father's modern design. Unfortunately, when he attends the school board meeting with his father, he witnesses Mr. Kowalski showcase Mr. Hoodhood's design as if it was his own. At first, Holling feels betrayed by Meryl Lee but comes to believe she is innocent and that her own father had betrayed her. When Mr. Kowalski withdraws his design, leaving the contract in Mr. Hoodhood's hands, Holling witnesses his father be jubilant, even jubilant about the fact that Kowalski and Associates, the livelihood of Holling's dear friend's father, is likely to go out of business. Having read The Merchant of Venice, Holling is able to reflect that his father, like Shylock, is not necessarily power hungry because he's money hungry. Instead, like Shylock, his father may behave like a power-hungry animal because he believes it is what society expects of him:

I suddenly wondered if my father was really like Shylock. Not because he loved ducats, but because he had become the person that everyone expected him to become. I wondered if he had ever had a choice, or if he had ever felt trapped. Or if he had ever imagined a different life. ("February")

Associating his father with Shylock helps Holling better understand his father, to see him as less of a villain and as more of a person trapped by circumstances and society's expectations. Hence, reading The Merchant of Venice served as a good lesson that taught Holling a new perspective and a new understanding of those who appear to be villains. Later, because of his lesson from The Merchant of Venice, Holling even stands up to his father by saying that to become a man is to choose whom you want to be.