"The real evil isn't the objects of technology but the tendency of technology to isolate people into lonely attitudes of objectivity."
(Robert M Pirsig, Zen And The Art Of Motorcycle Maintenance)
Unlike a lot of my friends in the tech industry, I don't generally get excited about new technologies. I do get excited when I see technology (or anything else) shifting the boundaries of social possibility in ways that make room for playfulness, serendipity, sociability between strangers or intimacy between friends. (For example, I got excited about Twitter when it started to lead to unexpected meetings with interesting people in the real world.)
This distinction is caught nicely in the comparison already made between Ivan Illich and Stewart Brand. In the late 60s and early 70s, both placed a deliberate emphasis on "tools": for Brand, this was about "access to tools" (the slogan of Whole Earth Catalog from its first edition in 1968), whereas Illich stresses the choice of Tools for Conviviality (1973), those technologies which will tend to produce the kind of world we would want to live in.
I can recommend David Gauntlett's Making is Connecting: The Social Meaning of Creativity (2011) as an exploration of the connections between Web 2.0, the resurgence of craft culture and Illich's critique of institutions. What struck me, reading it, was the way in which ideas Gauntlett brackets as utopian become more plausible, if we find ourselves in a world of long-term economic contraction.
A good practical counterpart is Hand Made: Portraits of emergent new community culture (2010), edited by Tessy Britton, which includes contributions from Gauntlett and myself.
In 2004, I stumbled across Ben Russell's Headmap Manifesto (1999) and it opened my eyes to the possibility that something bigger was going on with the internet than a vast electronic library, shopping mall and postal service. It's even weirder to go back and read it now that so many of the things Russell wrote about have become part of so many of our lives.
Another great read on the relationship between technology and reality is Indra Sinha's extraordinary book, The Cybergypsies, which threw itself off a library shelf at me around the same time. (It even includes a cameo appearance from Alastair McIntosh.)
Steve Talbott is a former Silicon Valley programmer who now writes about the social questions surrounding technology. Devices of the Soul is the sanest book I've read about the downsides of living in "the information age" and how we make sense of them.