I have to second "Hitchhiker's Guide" - I read at least the first volume every year - it helps to reassure me that the idiots that surround me at work are really idiots - and there's not much I can do to actually change things - but laugh at them and move on. It's reassuring in a snarky, really dark way about how things really are ... and might be destined to always be ....?
Second would be the "Winnie the Pooh" story collections - I think Pooh is one of the greatest philosophers of all time disguised as a child's toy - go back and really look at what he says in response to the others' dialogue - what he advocates for daily living and dealing with others.
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