This sounds like an interesting and worthwhile assignment. In writing your diary entries, you will be reviewing the plot, as well as studying Jem's character--how he thinks and expresses himself and how he changes during the story. You say you tried by "being Jem," and that is good! It means you are stepping into his character, assuming his identity, and writing from his point of view in his language. Listening to Jem is much different, for example, from listening to Atticus or Aunt Alexandra. As you write your entries, keep hearing his voice.
Since one entry must address a specific incident from the novel, choose one that Jem would remember very clearly because it was important to him. Some possible suggestions would be losing his pants on the Radley fence, losing control and destroying Mrs. Dubose's flowers, sitting in the courtroom and hearing the verdict in Tom Robinson's trial, or being attacked by Bob Ewell on the way home from the school pageant. Jem would surely remember each of these incidents in great detail, especially the last one when he fought to save his little sister's life.
When you write an entry about Jem's maturity, keep in mind that he is a dynamic character in the novel--he does change as he grows up. Look at Jem's thinking and behavior in the beginning of the novel, and contrast it with his thinking and behavior at the end of the story. Notice that as Jem matures, his relationship with Scout changes (sometimes this bothers her), and he becomes closer to his father in a different way. Growing up isn't easy for Jem; what he experiences sometimes makes him moody or very angry; sometimes he even cries in anger and frustration. In writing from Jem's mature point of view, think of what he has seen and heard in Maycomb throughout the story; think of how it has changed him. What would he have to say looking back?
Good luck with your assignment! I hope these suggestions are helpful. Also, the eNotes links below will take you to some excellent resources over Jem and the novel.
In Harper Lee's To Kill a Mockingbird, to write a diary entry, I would first find an incident to write about, and it sounds like it has to focus on Jem's maturity.
There are three incidents that come to mind regarding Jem's maturity. Maybe one of these will help.
When Jem destroys Mrs. Dubose's flowers, the biggest problem is that he is not mature enough at that point to listen to her criticisms of his father and ignore it, which would be the mature thing to do. However, like many things we master, we do so over time. In Chapter 11, when Jem is punished and must read to Mrs. Dubose each afternoon, she does not stop criticizing Atticus, but Scout reports that Jem has learned to hide his feelings.
'Don't mutter at me boy! You hold up your head and say yes ma'am. Don't...
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guess you feel like holding it up, though, with your father what he is.'
Jem's chin would come up, and he would gze at Mrs. Dubose with a face devoid of resentment. Through the weeks he had cultivated an expression of polite and detached interest, which he would present to her in answer to her most blood-curdling inventions.
Jem's ability to take whatever insult she dishes out shows his growing maturity. And in these situations, you could write about what he thinks when his face becomes unreadable, and even follow it up about his admiration for her in beating her morphine addiction.
The second situation, of course, it Jem learning to deal with the devastation he experiences when Tom Robinson loses in court. This is an especially bitter pill. You should look at his early responses and how he comes around, and see if that helps. (End of Chap. 21 and beginning of Chap. 22)
The last instance that comes to mind is in Chapter 28. Jem is particularly mindful of the sounds they hear as he and Scout return from the pageant at the school. He takes his responsibility in getting Scout home very seriously. Jem's determination to save his sister from their attacker is evident. He battles with the assailant, screaming for Scout to run. He is a youngster himself, but he is concerned for Scout as long as he is conscious.
In terms of using the correct language and diction, study how Jem and Scout speak (maybe even Dill). They are the three kids who will speak differently than Atticus, Miss Maudie and even Bob Ewell. I would mimic their manner of speaking: they make use of "ain't" quite often. And pay attention to their exclamations as well: "jee crawling hova" is something Scout says to Jem when he gets full of himself and tries to act like an adult and tell Scout what to do. (Chap. 14)
I hope that this information is of some help.