It's like hygiene. A few hundred years back people weren't washing their hands and health was very bad. As soon as we understood the germ theory of disease, we learned hygiene and now we are much better.

With encryption and privacy it will be the same. People will need to learn new skills.

Unfortunately, what we need to do is as cumbersome as a surgeon prepping for operation - it takes too much care to make sure you don't mix things up. You never login into your Gmail on Tor, don't refer to your reddit user name on Gmail, etc.

Unless you already did, in which case you're toast. They already have years of data on your views and interests.

Could we make a browser extension that would compare all you do and force privacy for you? For example, if you mistakenly mention your anonymous identity in your official mail, to catch it before sending. It should have a list of forbidden things - keywords, user names, etc - and send watch people not to mix the pots. Take care to separate cookies between anonymous mode and public mode. I am sure such an extension would go 99% of the way to making your private online life private again.

I envision a whole suite of apps - browser, mail, messaging, file sharing - written with this goal in mind - to separately manage identities - private and public - based on the content of communication. Like spam filters, but applied to all our data leaks.