I use TrueCrypt containers ("crypts") for my business and personal files. About 5 GB of files in two 5GB containers. My clients' information is confidential, and I believe that personal data on anything that is portable should be encrypted. Not to do so is just reckless.
Plus, TrueCrypt containers are nice and portable, and it is easy to make encrypted backups. If you encrypt on your drive, but do not encrypt backups, then there is not much point in encrypting.
I don't encrypt e-mail. I have not looked into it, but anything I use would have to be able to be decrypted without additional software or steps, or my clients will never bother to read it. I do require clients to use a personal e-mail address if they want to communicate with me, since they have little or no privacy interest in communications through a work e-mail address.
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