Worried that Bart is destined for failure, Marge turns to a series of parenting "experts" for advice. Homer decides to cash in on one expert's advice by opening up a trophy store in Springfield. Meanwhile, Bart finds some needed encouragement from Grampa, who gives him a precious watch coveted by Homer.
Bart is disecting a frog in a brusque manner to the horror of the frog's ghost who is watching from heaven, later Marge worries after seeing Bart's grades that he might be a failure so she decides to search up what to do and contacts an expert who tells them the problem is the kids low self esteem and tells them to shower them with trophies or certificates so they can feel special, this is seen as a good idea by everyone.
Bart wakes up with a trophy for being a good sleeper apparently, but Homer and Lisa are unsatisfied since Lisa belives trophies should be earned and it's just a waste of money, which gives Homer the idea to open up a trophy store, the store is a success and Homer earns alot of money aswell as placing Bart to work but he seems rather lazy at it, simply placing gum on them to stick together, while outside Bart overhears his parents discussing him, Homer says Bart can't do anything right and he's a ''screw up'' no matter how hard he tries, leaving Bart saddened.
Bart walks by the Retirement home where Abe tells him about how those words were used by him to Homer and to abe by his father and so on because of an apparent career for being a strangler, Abe then gives him a precious watch a heirloom so he can boost his self esteem, in the meantime Lisa grows tired of the trophies and breaks hers in defiance leading her to get detention where she discusses her problem with Willie where she gains an idea and gets another Child Expert who says that too much self esteem will lead kids to ruin and proposes G.R.I.T. (Get up, retry, i don't care if you're tired) which every parent now adopts, leading Homer to go out of business where he discovers that Bart has the watch which he has coveted for years, Bart's watch makes him stop doing bad decisions aswell as boosting his esteem but while playing with it the watch snaps and falls off a cliff.
Bart attempts to find the watch by throwing rocks but ends up injuring milhouse, in the meantime Lisa's plan works against her when Marge takes away all her trophies (although she earned them), leaving her defeated, Bart in the meantime attempts to hide the truth about the watch but Abe calls him saying that he and the watch will be appearing in Magazine, Bart decides not to tell him about the truth, Homer takes away all his trophies while discussing his failures with Lisa about how he wanted the watch, while at the Pawn shop however he finds the watch which was given to him by Milhouse who was mad at Bart for throwing rocks at him so Homer buys it for $22.
Homer attempts to rub it in Bart's face but after seeing him crying about the watch was the only thing that made him a success he gives him the watch reminding him about who ''screwed'' him up as those before him. Bart appears in the Magazine with the watch, Marge tells him what parenting guide he used to which he says to trust his G.U,T (give up trying) as Marge and Homer share a hug Bart breaks the watch and ends up getting strangled by Abe. The Final scene shows the NBA draft beginning and Ralph Wiggum being chosen for most trophies to Lisa's dissapointment as Ralph says he is a Millionare.