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 ringing from inside him and Smithers shoving a stick through his throat to answer the call.
* ContinuityNod: The couch gag shows that Springfield is still rebuilding from the events of ''Film/TheSimpsonsMovie''.
* DontTellMama: Homer doesn't want Marge to know he failed to get the new job.
* PunBasedTitle: The episode's title is based on a slogan Delta Airlines used from 1987 to 1992: "We Love to Fly and It Shows".
* SongParody: Homer requests Lionel Ritchie alter his song "Say You, Say Me" to "Hey You, Beer Me". Then he wants ''all'' the words to be "beer".
--> '''Homer/Lionel''': Beer beer, beer beer.
* 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.