There's obviously a lot of philosophers out there, but as far as I'm concerned, you can never go wrong with reading some Plato. It doesn't matter to me that I don't agree or understand every little thing he writes, but he's enjoyable to read and his words get me thinking.
I always recommend reading The Republic and the Phaedo. The Republic is not quite what you think, but will almost certainly be better than you think. In book VII is where you will find the well-known Allegory of the Cave, but that's only the smallest part of what it has to offer. Plato, as usual, has Socrates be the main character who is engaged in discussion with a few other people about what is necessary to create the ideal society. But this is no mere utopian account, since this book talks about the various aspects that make up a just society, and in doing so, helps us understand our own.


The Phaedo is the famous account of Socrates' death. This is his one last conversation with his friends and he is of course talking about life and death, the soul and the body, and how the true philosopher should live. Again, there is nothing but dialectic beauty in this book.
As you read through the various blogposts, I'll also highlight several other works of philosophy that are also worth your time.
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