A must read for everyone: The Beginning of Infinity by David Deutsch, which solves the question of all questions, how we can know what we know. The book draws out the implications of this idea for ethics, politics, and aesthetics, while also discussing maths, physics, and AI. All of this is written so clearly that you will find yourself understanding things which you can’t believe you ever failed to understand.
Thinking, Fast and Slow by Daniel Kahneman has been mentioned a few times and is definitely worth reading to realise that we humans aren’t as rational as we think we are. For the opposing viewpoint, you may want to check out Ecological Rationality by Gerd Gigerenzer, which contains papers discussing the importance and even comparative advantage of fast and frugal heuristics.
While we’re on psychology, The Stuff of Thought by Steven Pinker is a great read as well. It explains how the way we use language sheds light on the workings of our minds, and consequently our social relations as well.
This Will Make You Smarter by John Brockman contains short essays from top intellectuals around the world on important concepts. They are all available to read online here:
In the same vein is Daniel Dennett‘s latest, Intuition Pumps And Other Tools for Thinking, where Uncle Dan outlines some general thinking tools, and then a guided tour through his philosophical career with tools for thinking about meaning, evolution, consciousness, and free will.
For a quick survey of philosophical problems, check out Just the Arguments byMichael Bruce and Steven Barbone, which contains 100 arguments in the areas of religion, metaphysics, epistemology, ethics, mind, science, and language. Of course, it helps to have a good foundation in logical thinking, so if you’re unsure check out some introductory guides to logic. A good catalogue of fallacies is How to Win Every Argument by Madsen Pirie, although you could just as well plough through the Wikipedia.
If you would like to further explore the development of Western philosophical thought,Bertrand Russell‘s classic History of Western Philosophy is not a bad place to begin. For the other side of the story, check out The Truth About Everything byMatthew Stewart, appropriately subtitled An Irreverent History of Philosophy, in which pretty much every philosopher in history is cast as a villain because they were seduced by metaphysical speculation. If that leads you to wonder what role metaphysics can play in our thought, read Everything Must Go by James Ladyman and Don Ross, which deals with the appropriate metaphysics for a scientific, naturalistic worldview.
So what are the things that reason can never tell us about? Check out The Outer Limits of Reason by Noson Yanofsky for a guided tour through paradoxes and insoluble problems in logic, mathematics, and science.
Quite a few books by Nassim Taleb have already been mentioned, and I would just like to add his latest work Antifragile to the list, as it gives us a new way of thinking about and acting in the face of uncertainty in a whole range of domains. And if you want to know what can and cannot be forecasted and how to go about it, read The Signal and the Noise by Nate Silver.
A classic that is still relevant today is Metamagical Themas by Douglas Hofstadter. The book discusses almost everything, including alphabets, sentences, language, nonsense, art, mathematics, Rubik’s cubes, programming, cognitive science, law, and game theory. Everything is tied together by the theme of self-reference and reflexivity, making this a great book for learning to see the connections between seemingly unrelated things in the world.
If on a winter’s night, a traveller by Italo Calvino is a truly mind-expanding work of fiction. The protagonist’s reading is interrupted after the first chapter by a printing mistake, and attempting to replace the book at the bookstore leaves him with another book. But he will not get past the first chapter of that either… This book is a work of genius examining the processes of reading and writing, and the people involved in both. The prose is beautiful and perfectly suited to the task, reading at times almost like a conversation with the author. But the true conversation when reading this book will be with yourself, within your own head. If mind-expanding is what you’re looking for in your fiction, you will find no better.