While on a shopping trip to the Springfield Mall, Mr. Burns finds a penny in a water fountain and reaches in to grab it (fearing Ralph might take it) and falls in. The rushing water nearly drowns him, but Homer arrives and pulls him out of the water, saving Mr. Burns's life. To reward him, Mr. Burns offers to take Homer out to dinner. Homer says he likes Chicago deep dish pizza, so Mr. Burns takes him to Chicago on his private plane. On the plane, Homer is treated with luxury and gets serenaded by Lionel Richie. Homer has the time of his life in Chicago, but he becomes depressed on the return trip because he does not have the plane. Back in Springfield, Homer tells Marge that he is tired of being a normal person and becomes depressed. Marge, pitying for Homer, decides to help and hires him a life coach named Colby Kraus (Stephen Colbert), who will help with Homer's dream. Colby starts right away in his treatment with Homer by videotaping his every move. At the bowling alley and after watching Homer's daily habits for a few days, Colby realizes that bowling is the one thing Homer is good at and enjoys doing. He instructs Homer to wear his bowling shoes everywhere he goes to help instill confidence in everything he does. The bowling shoes work, Homer becomes a new man, and as a result he receives numerous new job offers. Homer decides to only go for an interview at Handyman's Choice Copper Tubing because he would be required to fly in the company jet as part of his new job, however, the Rich Texan does not hire him.
Homer decides not to tell his family and pretends to go to work every day, although he is actually just going to the local Krusty Burger. The next day, Bart's class stops at the Krusty Burger after a field trip and Bart is shocked to discover Homer sitting at a booth alone. Homer comes clean and explains to Bart that his job interview did not go so well when his interviewer, the Rich Texan, discovered that Homer knows nothing about copper tubing. Bart convinces Homer that he should tell Marge what has happened and Homer calls her from a pay phone. But when Homer hears Marge’s happy voice he cannot bring himself to disappoint her and tell her the truth about his "new" job. Instead he concocts a story about him having to fly on the "company" jet for work and instructs Marge to meet him at the airport in an hour. Homer pays a Marine to fly him into the air, so he can tell Marge up in the air with luxury so she would not get upset. Once in the air, Marge cannot believe all the luxuries the private jet has to offer. Homer sits Marge down to tell her the truth, but just before he can, the plane endures turbulence. Homer and Marge head into the cockpit to see what the problem is, only to discover that the pilot had passed out. Homer shoves the pilot aside and takes hold of the jet’s controls. As the jet is about to hit the ocean, Marge pulls the jet's yoke up giving the jet altitude. Marge pulls out her cell phone and calls Colby Kraus and frantically asks for his guidance. Thanks to Colby's motivation, Homer manages to land the plane safely on the ground, however, his attempt to taxi back to the terminal fails and the plane falls into the ocean. After being airlifted out of the plane, Homer explains to Marge that flying in private jets is simply too dangerous and that he plans to go back to work at the Power Plant.