I'd like to advertise my own book here on Ancient Greek thought but that would give away my identity :-/

Shakespeare, have you read The Consolation of Philosophy by Boethius? It might be down your road. I find analyzing, and prepping books for a dialogue in my own books very therapeutic. One of the aspects of philosophy that is too often left out is each writer's style of reading. Nietzsche with his aphorisms, Socrates with his irony, Hume's smooth as butter style, Wittgenstien's quirks, Aristotle's plain brilliance, Plato's dialogues, Cicero's fatherly advice. There should be a literature of philosophy course in general. My own style right now is to have a conversation with whatever topic but with 5 very distinct views from differently defining Greek gods so the reader can take whichever position they want.