Refreshing the playlist on my shuffle

My shuffle holds a subset of my songs. How can I easily refresh the playlist with a new batch of songs from my collection?
Update: Answer found here: https://discussions.apple.com/message/9911819#9911819

Just got this reply - my online access has been curtailed recently.
Thanks for the reply, I'm happy to see there's a solution out there.
I've started nosing around online to find some of these apps you mentioned, but haven't had much success. Any specific apps I should look into?

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    Please let me know if this is possible.
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