In non-web life we have private and public spaces and there's plenty of study on how these two play together and how important they are. Most people have erroneously thought that because your computer is in your private physical space that it's also 'private', but that's clearly not the case.
What people need is the education to create the technological equivalent of locking yourself in your bedroom for the afternoon to clear your head.
Gmail is like sending a postcard, facebook like chatting with friends at the mall or park. Tor/truecrypte/pgp etc for parts of your life you want private. Separate usernames, interests, tones of voice, etc in this private space.
Trying to hide your real (ie public) self is silly as should you become a target of the nsa & co. they'll find a way to dig up something even if you've been completely hidden from july 2013 on. What people need is a reasonably benign public self and a hidden crypto-self.
Also I'm all for fighting the surveillance state, but I'm extremely cynical of it's success. I see no feasible way to reduce the power and authority of the militarized aspects of our government(s). I can't think of a single example of where public knowledge and outcry has changed anything other than getting a few puppets punished anywhere except the non-militarized parts of government.