For securing files on your computer I suggest using Disk Copy (from Apple) to create an encrypted disk image upon which you then store your files. It basically takes a chunk of your hard drive, treats it like a separate drive and encrypts everything in that chunk.
For encrypting email the MacGPG project is coming along quite nicely. It does, however, require some comfort with the command line and the UI of some of the elements leave a lot to be desired. I'd recommend installing MacGPG and then the following email utils and then forgetting about it. There's also quite an active mailing list available.
To use GPG with Mail.app you'll want GPGMail.
To use GPG with Entourage you'll want EntourageGPG. Note that in both cases, for Mail.app and Entourage, you need to have installed and configured MacGPG first.
For securely shredding files under X... I don't know. If you've got any suggestions for an app that works well, securely and doesn't causes file system trauma let me know. Discuss