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Socrates recommends in the Republic that youth spend time in military service and business, and hold off on doing philosophy until they are around 40 and know a bit more about how the world works.

Actually, Plato paints a very conservative society in the Republic, and even more so in the Laws. However the general picture from the Socratic dialogues isn't so clear cut; Socrates' interlocutors are mostly young people (Phaedrus, Alcibiades, and the likes), and for a part stubborn older people, rhetors, politicians, etc. not really as eager to learn as the young :)

Quite true. Socrates is often saving young people from either being practicality oriented people who can't think like Cephalus, or philosophers who don't matter or are evil like the sophists.

Yet he takes two aspiring young warriors, and converts them to philosophy. Socrates' philosophy was not at all dependent on knowing anything about how the world works: in fact, those shadows were considered harmful.

That's true that he convinces the youth of the value of philosophy. But, that doesn't mean there wasn't any value to the rest of life. In fact, it may give the rest of life more value, since the rest of life can be lived in light of the importance of philosophy. Socrates himself served in combat, and was noted for his bravery (recounted in Symposium). If memory serves, he attributed this bravery to his interest in philosophy.

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