Hook up your pocketpod to your computer.

From your desktop, go to Start>My Computer, your player should be listed as one of the drives. Double click on it and it'll open your player. Now open the folder with your files in it(usually your Shared folder, located at C:\Documents and Settings\"your account name"\Shared). Or just open LW and go to the library page click on your shared folder then click the explore button. Your shared folder will open up and from there you can drag the files to your pocketpod window.

Drag files from one folder to the other by left clicking on them and while keeping the mouse button held down, move the cursor to the other folder and let go of the button(or copy and paste). Windows will automatically add the files to your player. You can move many files at once by by highlighting them and then drag them to the other folder.

__________________
If it ain't broke, fix it till it is!