[source: http://www.paulgraham.com/raq.html]What should I read to learn more about history?
The way to do it is piecemeal. You could just sit down and try reading Roberts's History of the World
cover to cover, but you'd probably lose interest. I think it's a better plan to read books about specific topics, even if you don't understand everything the first time through.
Here are the most exciting ones I can think of:
White, Medieval Technology and Social Change
McEvedy, Penguin Atlases of Ancient and Medieval History
Laslett, The World We Have Lost
Bernal, The Extension of Man
Girouard, Life in the English Country House
Pirenne, Mohammed and Charlemagne
Runciman, The Fall of Constantinople
Cipolla, Guns, Sails and Empires
Hadas, A History of Rome
Oman, The Art of War in the Middle Ages
Vasari, Lives of the Artists
Bovill, The Golden Trade of the Moors
Caesar, Gallic Wars
Kuhn, The Copernican RevolutionWhat philosophy books would you recommend?
I can't think of any I'd recommend. What I learned from trying to study philosophy is that the place to look is in other fields. If you understand math or history or aeronautical engineering very well, the most abstract of the things you know are what philosophy is supposed to be teaching. Books on philosophy per se are either highly technical stuff that doesn't matter much, or vague concatenations of abstractions their own authors didn't fully understand (e.g. Hegel).
It can be interesting to study ancient philosophy, but more as a kind of accident report than to teach you anything useful.