As with pretty much everything else, this actually happened, though it wasn't my boss and it wasn't via email.
A couple of weeks ago I found an envelope in my mail slot in the main office. When I opened it, I found four sheets off a Dilbert desk calendar, all about an in-office cartoonist (see below). Attached was a note that said "Thought of the TFRL master when I saw these." I had no idea that the person who signed their name even knew about TFRL. I guess my reputation precedes me.
However, I do know that my boss reads TFRL. He's never said so, but sometimes he'll say something in our weekly meetings that reflects on the events in TFRL. And of course, our CIO knows about TFRL. Not sure it's in his Google Reader though. I rather hope not.
Anyway, though I appreciate the pageviews, it does put a lot of pressure on me to not hit too close to home on anything. I have to walk a very fine line with TFRL now while keeping it real and funny, and that's a lot harder than you might think.
Fortunately, my boss has never done anything TFRL worthy (though I'm told I do a pretty good imitation of him). He's appeared a few times in TFRL (he even laid me off a few weeks ago), but his 'character' isn't really him as much as it is a generic boss. As for our CIO, I try to not know too much about what goes on in his office.
Here are the Dilbert cartoons...