Homer gets a life coach (voiced by [[TheColbertReport Stephen Colbert]]) after realizing that he wants to be rich and successful enough to buy his own private jet.

!! Tropes:

* BrickJoke: At the beginning of the episode, it's revealed that Mr. Burns ate a mini-cellphone because he mistook it for a lemon drop. A later scene has the phone fringing from him and Smithers shoving a stick through his throat to answer the call.
* DontTellMama: Homer doesn't want Marge to know he failed to get the new job.
* TakeThat: According to a play that Homer and Mr. Burns watch in Chicago, Starbucks charges a billion dollars for a cup of coffee.
* TooDumbToLive: After landing a plane, Homer decides to drive it to a proper place and ends up sending it to the sea.