Worried that Bart is destined for failure, Marge turns to a series of parenting "experts" for advice. Homer chooses 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, after observing Bart's grades, Marge worries that he might be a failure, so she plans to make a search of what to do and contacts an expert, who tells all of the parents at her presentation that the problem with their children is their low self esteem, and suggests them to shower their children with trophies or certificates so they can feel special. Eventually, all the parents think that this is a great idea.
The next morning, Bart wakes up with a trophy for being a good sleeper apparently, but Homer and Lisa are unsatisfied since Lisa believes that trophies should be earned and it's just a waste of money, which gives Homer the idea to open up a trophy store in the garage. It turns out that the store is a success and Homer earns alot of money, as well as placing Bart to work. But, he seems rather lazy at it, because all he does is simply placing chewing gum on them to stick together. While Bart overhears his parents discussing him from outside, Homer says that Bart can't do anything right and that he's a ''screw up'' no matter how hard he tries, leaving Bart crestfallen.
The next day, Bart sadly walks by the retirement home, where Grampa gives him advice and tells Bart about how those words were used by him to Homer and to Grampa by his father, Orville Simpson, and so on, because of an apparent career for being a strangler. Grampa then gives him his precious watch, the Baumont Chrono-master Elite pocket watch, which is a long-time Simpson heirloom that boosts Bart's self esteem when he touches it. Meanwhile, Lisa grows tired of the trophies, because she has gotten the smallest trophy while Ralph has gotten the big one, even though he was in last place. Jealous, she breaks her trophy 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 to all the parents at his presentation that too much self esteem creates millennials, which is a generation of soft, entitled narcissists who drop out of college to become DJs. He then suggests to all the parents that instead of showering their kids with gifts, they should prod them to greatness with G.R.I.T. (Get up. Retry. I don't care if you're tired; aka Get Rid of Idiotic Trophies.) which every parent now adopts, causing Homer to go out of business after he gets booed at by the other parents while trying to give trophies. He discovers that Bart has the watch, which he has coveted for years. In a montage, Bart's watch makes him stop preforming bad manners, as well as boosting his self esteem, but while he jumps with joy on a cliff, he accidentally drops the watch down the cliff, making Bart upset while Homer's voice sings a parody of "You're the Best" inside his head.
Bart attempts to find the watch by throwing rocks down the cliff, but ends up injuring Milhouse, even though he says that not a single one missed him. Later, Lisa's plan works against her when Marge takes away all her trophies (although she earned them), leaving her defeated and upset. Meanwhile, Bart attempts to hide the truth about the watch, but Grampa calls him saying that he, Grampa, and the watch will be appearing in Remember That Magazine. When Bart chooses to not to tell him about the truth, Homer takes away all of his trophies while discussing his failures with Lisa about how he wanted the watch. However, while he is selling the trophies at Frank Needy & Sons Pawn Shop, he finds the watch in the glass display, which was given to Dumlee, the pawn shop owner, by Milhouse, who was mad at Bart for throwing rocks at him, so Homer buys it for 22 dollars and greedily exits the pawn shop with the watch in hand while maniacally laughing.
Later, Homer attempts to rub it in Bart's face, but after seeing him crying about the watch that was the only thing that made him a success (with Santa's Little Helper comforting him), he gives him the watch and reminds him about who ''screwed'' him up as those before him, with the spirits of a young Grampa getting strangled by Orville, who is getting strangled by "Old Tut" Simpson.
The next day, Bart and Grampa take their cover picture for Remember That Magazine, with the watch in Bart's hand. As Bart spends some quality time with Grampa, Marge tells Homer that it was a nice thing he did to Bart, and then asks him what parenting guide he used to do it, so Homer answers that sometimes, you just got to trust your G.U.T (Give Up Trying). As Marge and Homer share a hug, Bart accidentally breaks the watch and ends up getting strangled by Grampa. It turns out that the whole episode was published in a book of the same name, which was written by Homer himself.
Before the rest of the end credits, Homer and Lisa watch the NBA draft, and it turns out that Ralph Wiggum was chosen for the most trophies in his class compared to the others, much to Lisa's disappointment. After Adam Silver announces that Ralph is the winner, he comes up on stage (with his proud parents by his side), shakes Adam's hand, and says that he's a millionaire as he gets his picture taken.