Email is tricky. For most people, Thunderbird plus EnigMail is probably the best option, but it is confusing to use and it also “leaks” information (as will always be the case for email sent through traditional channels). Various projects to fix email were announced in the wake of the Snowden revelations, but the onse I know about have mostly stopped development. It’s a hard nut to crack.
Still: you should aim to encrypt a relatively high percentage of your emails if you can. It’s not good enough to just encrypt a few; the important ones need to be masked by the trivial ones. And encrypting your emails also helps to protect the journalists, activists, ando thers who need to encrypt their communication for their own protection. We encrypt not just for ourselves, but to preserve essential freedoms for others.
Over the next few months I hope to transition to encryption in most of my messaging; that means that, if you want to be in touch with me online, you’ll need to start figuring this stuff out too. Let me know what I can do to help!