The main character in "Dear Mr. Henshaw", Leigh Botts, learns a lot about problem solving during the course of the narrative. Leigh aspires to be a writer when he grows up, so he works to eliminate the obstacles to that dream by practicing, sometimes even against his will. Mr. Henshaw's list of questions helps Leigh in this respect, and even though he answers the questions under duress, his writing improves because of his hard work. Leigh wants to enter a writing contest, but finds he is not ready to write an imaginary story. He overcomes this problem by focusing on the things he can do, and writes a nonfiction piece instead. His entry is picked as a runner-up, and when the first-place winner is eliminated, he receives a prize in her place. Leigh learns that being proactive helps him solve a lot of his problems. When his lunch is being pilfered at school, he invents a lunch box alarm to thwart the petty thief.
Leigh's main problem, though, is not one he can solve in the way he would like to. Leigh wishes that his father would be there for him, and that he and his mother would get married again. It is not to be, however, and Leigh discovers that, in order to solve this problem, he must learn to accept some things the way they are. When he comes to terms with this reality, Leigh takes a giant step towards maturity, and feels "sad and a whole lot better at the same time" (Saturday March 31).