In To Kill a Mockingbird, Atticus wants his children to learn how to see from other people's perspectives so they can better understand them and have compassion on them. In fact, he tells Scout and Jem that "you never really know a man until you stand in his shoes and walk around in them."
Jem learns this lesson more than once in the story. When Jem loses his temper and destroys Mrs. Dubose's flowers, Atticus makes him go to her house and read to her every day for a month. Jem gradually comes to understand Mrs. Dubose better as he obeys his father. Later, though, Jem learns more about Mrs. Dubose and her struggles when Atticus tells him that the old woman had been a morphine addict but was determined to take herself off the drug even if that meant more suffering. Jem finally realizes why Mrs. Dubose can get nasty and why she has fits. He stands for just a moment in her shoes.
Jem also puts himself in the shoes of Tom Robinson after the jury returns its highly unjust guilty verdict. Jem is horrified. He knows that Tom is innocent, and he has just witnessed Atticus build a strong case that shows beyond a reasonable doubt that Tom never assaulted Mayella Ewell. In fact, Atticus clearly demonstrates that the Ewells are lying. Yet the jury convicts Tom anyway, merely because of his race. Jem can hardly handle the unfairness of it. "It ain't right," he declares as he starts to cry. Here, Jem identifies with Tom Robinson in his pain and grief and sees clearly the prejudice of some of Maycomb's white citizens.
By the end of the novel, Jem is also able to place himself in Boo Radley's shoes. After he witnesses the nasty behavior of the Ewells and the unjust verdict, he tells Scout,
I'm think I'm beginning to understand why Boo Radley's stayed shut up in the house all this time ... it's because he wants to stay inside.
Jem is starting to see the world at least a little bit from Boo's perspective.
The strongest example of Jem understanding what it is to walk in someone else's shoes is his response to the guilty verdict at Tom Robinson's trial:
It was Jem's turn to cry. His face was streaked with angry tears as we made our way through the cheerful crowd. "It ain't right," he muttered.
Jem cries because he has been rooting for Tom Robinson, as well as Atticus, during the trial. This siding with Robinson is significant, because Jem is white and Tom is Black. Most white people in the racist Maycomb community side with their fellow white people and turn a blind eye to the injustice occurring. Jem, however, listens to the case objectively and evaluates the situation on the basis of the evidence. Because Atticus has been persecuted for taking on the case and making a real defense of Robinson, Jem can understand what it is feels like to be...
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the persecuted underdog.
The guilty verdict shatters Jem's faith in the white adults in Maycomb, people he had looked up to until this point. However, near the end of the novel, it helps him walk in Boo Radley's shoes and understand why Boo might have withdrawn from social interaction. He realizes that sometimes isolation is not monstrous, but a rational response to a hurtful situation.
It should be pointed, however, that through much of the novel, Jem is struggling with entering adolescence, a situation which makes him more self-absorbed than the younger Scout.
After the Tom Robinson trial, Jem displays his empathy--walking in Tom's shoes--as he asks his father, "How could they do that?" about the jury's guilty verdict. He is incredulous that seemingly reasonable men could convict Tom Robinson solely because he is black and made the mistake of saying that he felt sorry for Mayella.
The experience with Mrs. Dubose helps Jem learn that people are not always what they seem. He thinks she is just a mean old lady, until he learns about her morphine addiction and that she is dying. This ultimately helps him empathize with Tom Robison and Atticus, which is why he cries at the verdict.
Following Atticus's killing of the mad dog in Chapter 10, Jem and Scout see once and for all that their father is neither feeble nor untalented. Jem proudly announces that "Atticus is a gentleman, just like me!"
In chapter 23 of To Kill A Mockingbird, Bob Ewell spits in Atticus Finch's face. When Atticus explains to Jem about his decision to walk away from a fight, Atticus asks Jem to consider how Bob Ewell felt after the trial. In the following quote, Atticus is asking Jem to walk in Bob Ewell's shoes:
"Jem, see if you can stand in Bob Ewell's shoes a minute. I destroyed his last shred of credibility at that trial, if he had any to begin with. The man had to have some kind of comeback, his kind always does. So if spitting in my face and threatening me saved Mayella Ewell one extra beating, that's something I'll gladly take. He had to take it out on somebody and I'd rather it be me than that houseful of children out there."
Chapter 23 pg 218
At the end of chapter 23, Jem and Scout are talking about the different kinds of people in the world. Jem is despairing a little about the condition of humanity, because some people are so unkind (like Bob Ewell). At the end of the chapter he says,
Scout, I think I'm beginning to understand something. I think I'm beginning to understand why Boo Radley's stayed shut up in the house all this time . . . it's because he wants to stay inside.
For the first time, Jem is showing some understanding and compassion for the neighbor that he has treated like a monster.