Surely we can agree that the director of the CIA is going to be better a maintaining privacy than the average person.
"Deutch left the CIA on December 15, 1996 and later that year it was revealed that several of his laptop computers contained classified materials designated as unclassified."
Specifically, he took sensitive compartmented information (SCI, http://en.wikipedia.org/wiki/Sensitive_Compartmented_Informa...), stuff which was covered by special access programs (http://en.wikipedia.org/wiki/Special_access_program) that required you to acknowledge each time you accessed it that it was so, and that you not leave the secured area with it, and put it on his personal PCs connected to the Internet, which he used to write up stuff which he emailed, again over that unsecured Internet, to people in the Clinton White House.
It's hard to express just how bad this is, not to mention how this angered the community of people with "tickets" (clearances, which, BTW, I've supplied recommendations for two of my friends, one who went to the NSA, the other with a TS/SCI ... which I know nothing about, except we can and do discuss which technology he's using (e.g. Microsoft)).
I would hope "the average person", after getting the usual training, and signing off on access to SCI, would understand and follow the simple idea that "Don't take it out of this room" means exactly that.
"The average person" would, I think, know he wouldn't be protected from prosecution by political pull if he violated that simple, white line rule....
At first you would want to encrypt the information. Then you would like to have some method of transfer that does not stick out and could hide the intent to transfer encrypted data. Perhaps with the help of some steganography tool. And you would make sure that nobody identifies you in the process by using tools like Tor. This "I hope they don't notice" method is just gambling.