Why was writing the screenplay so tricky, where I am still struggling to make it sound good?

I arrived at 3 main reasons, characterization, personal connection, and chronology.

Characterization:

Given more time, I would have really liked to develop the characters more. Butler was fairly developed, but understanding his backstory would have made it much easier to write in his voice. Outside of knowing he went to that same school, I didn’t really know his experiences after the fact, or what he really did when he got out of the community. Part of me sometimes felt like I was writing him in my voice. The president and parent were characters I wasn’t even thinking of until after the first draft of the scene. In fact, I never even anticipated there being a parent with actual lines of dialogue. Because of this and because of the time spent trying to make the dialogue flow well or sound somewhat melodic, I did not put in the proper time to flesh out the other characters.

Personal Connection:

There is no question that religion and education is one of the issues today I feel most passionate about. I have been talking about it for years. However, this is not a terribly personal film. For a first-time screenwriter, it seems much easier to write about what you know and what you have experienced. Outside of having some extended family members in that community, I never experienced those schools. I never had to figure out how to escape my community to learn what I wanted to learn. Perhaps as I write more and more that personal connection can become more diluted while still maintaining the quality of the script.

Chronology:

I saw a very interesting Quentin Tarantino interview that I will link below. He is one of the all-time greatest screenwriters and it’s not a coincidence that he also has written some of the best characters to ever grace the screen. One of the things he says he does while writing is that he doesn’t really plan it out all that much, but lets the characters drive the story. He stays so true to his characters that he lets them pick the direction of the film, because what Tarantino wants might not actually be what the character would do or say. For this reason, it is very important for him to write his scripts chronologically. Of course, he also does extensive characterization work and has a great deal of experience. Looking back on my writing, I wrote one of the final scenes of the movie first. That is the general direction I wanted it to go in, but if I wrote the whole screenplay, it very well could have ended differently as I learned more about my characters. I can say that at the very least, the dialogue would have probably been very different in that scene. I think moving forward, it is important not to fixate on one particular ending or one scene, but to work chronologically and see where the characters end up.

He says this in multiple interviews but here is a good concise clip: