Playlist too big for Ipod shuffle

I've been happily using a 2nd gen shuffle and it selects songs from my favorite playlist. The playlist is 2000 songs, and obviously doesn't fit on that shuffle, but the shuffle just randomly picks songs from that specific playlist. Now I have a 3rd gen shuffle, and I get a pop up saying that my playlist is too big. It asks if I would like itunes to randomly select songs. If I check yes, which is what I want it to do, it deselects that playlist and starts selecting from our 10000 song library. Isn't there any way to have it randomly select from a specific playlist? I'm tired of trimming down playlists for all these products. Just make it easier and do it for me like it does for the 1st and 2nd gen shuffles. Any help?