Sons of Liberty is right. I don’t think that reading one book will cause the proverbial light to switch on. It’s more like each book draws you closer to the light.
I was always a political nomad. At various points in my life, I considered myself a liberal or a conservative, but I’ve always had reservations and concerns about the positions that both sides took on certain issues. I’ve always been a fiscal conservative, but didn’t believe that the State should be involved in our personal lives so long as our actions weren’t harming anyone else. Likewise, I’ve always considered the Bill of Rights absolutely sacrosanct and was a big civil libertarian, which I thought was a liberal position, but I believed that individuals should be able to keep the fruit of their labor and never bought into the whole “redistribution” of wealth thing.
Then a friend told me that I sounded like a libertarian and encouraged me to check out the Libertarian Party, which I did. I discovered that I agreed with the libertarians on most of the issues and realized that I’d found a home. Although I now understood that there was more to the political spectrum than the Left/Right paradigm, I still wasn’t thinking in terms of philosophy, but rather “do I agree with them on this issue or that issue?”
A few years later, 9/11 happened. That terrible event really motivated me to give politics some hard thought. How could something like this happen? Especially in America? Unfortunately, like Sons of Liberty, I began down the neocon path. However, I did so for what I thought were pragmatic reasons. I’ve always considered people as individuals with equal rights, not as members of some tribe or group who are, by definition, “THE ENEMY!” Hence, I thought that war was a terrible thing, but that it was necessary, although I knew that innocent people would die and I was uncomfortable with talk like “we should turn Afghanistan into a parking lot.” Meanwhile, another part of my mind was still traveling down the libertarian path.
So I read all that I could, listened to podcasts, etc. I found myself more and more drawn towards libertarianism as not only philosophically attractive, but as the only system of politics that would really work. Then I discovered Rothbard and it was all over. I realized that private property anarchy, the stateless society, was not only possible, it is superior to any other political system. And it is the only truly moral arrangement for human society.
In addition to the great books that have already been listed, I’d like to add Mary Ruwart’s Healing Our World: In an Age of Aggression, especially if you want to approach things from the Left. For those interested in hard numbers and empirical examples, there is Harry Browne’s Why Government Doesn’t Work which resonates with our friends on the Right. I’d also like to recommend Richard Maybury’s Uncle Eric series, especially for young people. The drawback with the Uncle Eric books is that each short book covers a single topic and they are a little expensive, so accumulating the entire series can be a somewhat pricey.