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His "Goodbye to All That" is a good memoir of the First World War. Though his Mythologies are the most readable or engaging one. I prefer Thomas Bullfinch for Mythology.

I've read bios and/or seen interviews with a lot of famous older people. Invariably they mention that the best things in their lives were not about money at all. Just today I was reading that Edith Hamilton ('Mythology') was happiest about being made a citizen of Athens. Joe Campbell mentioned a race in college. Etc.

Money seems to be the best thing for people who need to feel secure. But for many people, who thrive despite the ups and downs of an insecure life, 'happiness' is found in intangibles... relationships instead of things. Family. Friends. Music. The outdoors. The arts.

My own 'best time' actually happened when I'd just left college and had almost nothing. 'Travel' meant thumbing a ride. Of course, being young, healthy and free is great. Also you don't know so much, and sometimes ignorance IS bliss. And sometimes we let ourselves get saddled with too many responsibilities, which can be a burden for a conscientious person.

Well depends on what you consider classics :-)
Go to a second hand shop, bookstore where they sell used books and get whatever you like.
Here is a small list that IMHO would appeal to many HN readers:
- Isaac Asimov (foundation trilogy, robot series, short stories compilations)
- William Gibson (nauromancer, bridge trilogy)
- Douglas Adams (The Hitchhiker's Guide to the Galaxy)
- Alfred Bester (The Demolished Man, The Stars My Destination)
- Neal Stephenson (Snow Crash, Cryptonomicon)
- Orson Scott Card (Ender’s game, Speaker for the Dead)
- Fyodor Dostoevsky (Crime and punishment, the idiot, notes from the underground and many more)
- Plato (apology, the republic)
- Bible, Torah, Quran and any other sacred text
- Mythology (Greek, Indian, Norse and o5hers)
And a last one, completely unrelated...
- Clive Barker (Hellraiser series, books of blood)

You may also enjoy two books by Edith Hamilton as more "preparation":

"Mythology" is a summary of the most common "stories" of Greek and Roman (and a bit Norse) mythology, good to understand contents and allusions.

"The Greek Way" is her "love letter" to Greece - why it was (according to her) better than our society, the differences in general thinking compared to Egyptians, Hindus, and "us modern Westerners", why we still have much to learn from the Greek.