Ok, so we all know that playlists cannot be transferred from iTunes. On my iPod I used playlists quite a lot as I listen to music by type of mood/activity (using the comments box to create smart playlists), eg music for working out or music for chilling out.
I am sure that I am not the first one who has come up with this way of creating a sort of playlist on the Clip:
On my Mac I open the Clip and inside the Music folder I create a New Folder, eg one named RUN. Then I drag Artists/Songs I already have on the Clip and which I like to listen to while running to this folder. Now when I go running I select Shuffle mode and select this folder > Play All and I can listen to songs from the many artists I like to run to. Voila, a sort of playlist!
Happy running/chilling/falling asleep/etc!