Cheerilee deals with being retired and seemingly having nothing really left to do in Equestria, perhaps her passed students can teach her a lesson in turn.

I had to do some timeline chopping to get it to work but nothing major, just some movements of years.

I had to toss in a handful of OCs for her students/famous writers/poets but I didn't list it because the story is about Cheerilee, not them. And technically the last non canon pony is actually taken from one of her students seen in the show but I had to give her a name.