A new look at Encrypted Email and Chat
This post is inspired by a changing landscape, the most recent of which is Google's announcement of an end-to-end encryption tool.
For non-geeks, what Google is doing is at least a good starting point. As pointed out on one of the security lists I receive, "granny can use it" and "it will get others thinking seriously about encryption". That's two good things.
Another tool that is easy to use is Cryptocat. It is a browser plugin that allows you to have encrypted chat sessions -- both one-to-one and with chat rooms. The big plus with Cryptocat is that it is available for a host of web browsers. It is also available as an application on the iPhone and will be available for Android soon.
For the geekier, Mailpile is getting close. It is a Mail User Agent (MUA) with built-in encryption. That means that if you have your mail stored locally (probably grabbing it from a server using POP3), it can do what you need. If you didn't understand this paragraph, Mailpile is not for you -- yet.
Finally, some folks at CERN have created a non-free encrypted mail service called ProtonMail. They have a free beta out right now but clearly they are swamped with requests. Also, unlike all the other software I have mentioned, ProtonMail is not open source meaning it can not be audited.