There is very little stored data that I bother to encrypt; most of it is "safe enough" sitting in my computer in a locked house, needing a password to log in. Anything that's
really private goes into TrueCrypt, which seems to me to be better thought-out than others (e.g., it's plausible deniability features).
For just a couple of files on my PocketPC, I use
CryptoStorage (
http://www.sinantech.com/products.htm), which is the same kind of volume container thing. The software is great, their customer support is non-existent, as far as I can see.
I
would use encryption on my email just on general principles, but the network effect hobbles this -- very few people actually have the software to do this, or even to understand what's going on.
Don't forget that the other side of encryption's coin is digital signatures. I have used
this many times in communicating with clients. I don't care if they can't verify the signature themselves; the fact that it's there at all would allow me to prove the accuracy of my story in court (should the need ever arise; it never has).