Is this possible to do with my ipod touch on itunes?

Hello there,
In work, myself and some colleagues do a "no skip friday" - we shuffle the entire playlist and are not allowed to skip tracks until the end of the day. A little silly, yes, but it means we keep rediscovering songs we never knew we owned.
My question is - I aim to make this a little more random. I'd like to randomly fill my ipod on friday morning with songs from my library, then when I come home, put the original songs back on my ipod. I think that, if I created a playlist with my current ipod library on it, synced it with my pc, then did autofill (although this advice came from an owner of an ipod shuffle, I'm not sure if this is available to the touch) - and when I'm done with the randomness, I can put the old playlist back on?
Hope this makes sense...

+if I created a playlist with my current ipod library on it, synced it with my pc+,
This is the step I'm not too sure about. Since I don't have an iTouch. I have a nano, and when I plug it in, the music tab has a checkbox to automatically fill free space. So, I could check that for the Friday experiment and then uncheck it when I was done, and not bother making some kind of playlist htat has what is already getting synced to the nano.

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