Some net tech I was just talking to told me he tors into everything. I don't know what the fuck he's doing that he's hiding his stuff (other than being one of the "really lucky" guys in life, but the poor are too stupid to fuck those people up anyway), but he just says "I like the anonymity".
If you only use encryption/VPN/TOR when you are doing something you don't want the authorities to know about, then the simple fact that you start using these things is enough to tip them off that you are up to something - even if they don't know exactly what it is.
The effectiveness of anonymizing technologies is dramatically greater when they are used for everything. It is a massively harder task for the NSA to decrypt and analyze every single scrap of traffic you send, than it is for them to decrypt and analyze only the tiny fraction of traffic you choose to encrypt because it contains something you want to keep secret.
The occasional use of security is itself a security risk - you might as well send the FBI an email saying "I am now doing something dodgy" each time your data suddenly becomes untraceable or unreadable. But if untraceable and unreadable is the norm, the change from sending emails to your mum on her birthday, to sending emails to your co-conspirators in a sinister plot, is seamless and unremarkable.
