I'm fairly tech savvy (ok, I'm an expert compared to my non-tech family and friends, but not compared to people here). I even had a copy of pgp on my Windows 3.1 machine shortly after Phil Zimmerman created it. I didn't understand it then, and I don't want to understand it now. The better and easier solution has been to avoid putting stuff I don't want anyone to know about me on the internet.

I'm a linux sysadmin, and GPG is horrible. Complicated, complex, with weird naming scheme, multiple programs (gpg vs gpg2), etc - but it's a brilliant example why all of this is so complicated. Other ideas about describing the trouble trust means on the internet are welcome.