For example, a book with 500+ questions in them where you are supposed to read the questions and answer them, just to get a glimpse of what your motives and values are by your answers. What are some books like that that are good? Questions books similiar to the one i’m describing sound pretty good for this sort of thing.
Have you already tried The Book of Questions. It is like you describe only there are only about 300 questions in it. It is very entertaining and can lead to introspection on some of the questions.
How about Walker Percy, Lost in the Cosmos?
Maybe a bit outside the box…