I've generally been somewhat blase about modern, targeted advertising. Our discomfort with the practice seems rooted in a misguided anthropomorphizing of technology. No one is "reading" your Gmail when an algorithm scans it for keywords.
Doc Searls’s piece makes some interesting points, though. The arms race between advertisers and ad-blocking technologies doesn’t seem likely to ceasefire any time soon. It reminds me of the early days of file-sharing, with Napster driving music companies to sue their customers. Clearly people are willing to tolerate certain kinds of ads. But when market feedback so clearly rejects this new generation, maybe advertisers ought to take the hint and back off before their whole industry goes down.
Is this a prisoner’s dilemma, though? Unlike the music industry (where anyone could have created iTunes at any time), there is no obvious path for unilateral disarmament that isn’t basically suicidal. It may be that the answer, then, is that consumers should be directing their anger at the advertisers (and maybe the publishers?) rather than the ad delivery systems. That would create market opportunities for non-creepy ad networks, and could plausibly roll back the trend before it’s too late.