Jaron Lanier's "You are not a Gadget"
(jaronlanier.com)
I finished reading this book earlier today.
It challenges a lot of the established and currently popular trends in digital culture and the Internet.
Personally I found it a breath of fresh air, against the predominant group think amongst hacker circles. Whether you agree with Lanier's viewpoints or not, I think they make for a great way to evaluate and consider where the state of the art is now, and where it is or should be heading.
Highly recommended.
