[mindslight]

(for context, I hope for both the NSA and Facebook to go out of business, and was recently thinking Snowden might make a good Schelling point for a write-in candidate)

There's always going to be collection of selective disclosure. Some of that could be changed by a culture of secrecy (youtube videos in skimasks ^_^), but in general there will be people who post everything to the friendster du jour. And I don't see how one could ever stop assuming that information will be archived indefinitely. For this, my hope can only be for a symmetric Brinworld transparency where it ultimately doesn't matter (and to the extent some does, people learn to navigate these contours).

But for stuff that doesn't need to be shared, I think you're focused too much on the NSA, when it's really just the most prominent example. Any sufficiently-funded intelligence agency is going to have plants that work at significant corporate information troves. Exfiltration isn't terribly hard when companies setup geographically diverse data centers on purpose.

And as I said, insurance companies are a far more worrying threat to me as far as dictating everyday terms of your life - "we noticed you buy an awful lot of beer. Your auto insurance rates will be doubling unless you let us install a GPS-enabled breathalyzer in your car". I suppose this could be held back with legislation if we had a working political process, but I also recognize that economics tends to win out regardless.

You say 'devolve' when talking about moving to non-centralized services, but this is a loaded term. I view web toys (also a loaded term, heh heh) as a stop off from the Internet becoming mainstream-recognized before its application technologies were really polished to withstand model precession. There's no reason privacy-preserving technology couldn't have a similar interface, yet be easily self-administered with the help of any friend who is just slightly savvy (besides that it's much harder to get such software funded when there's no point for capital to invest because it rightly takes the middlemen out of the picture).