iPod Pressing the Play Button

In the morning, I take my iPod off the USB Dock, and take it to work. My desire is to continue playing the shuffled music from where I left off yesterday, but I haven't figured that out yet. I go down to Shuffle, press the round button, and see shuffled song #1. I press the play button, and it has the equal sign and "Now Playing" indicator. But it doesn't play. I keep pushing the play button various speeds, sometimes making my iPod go black. It takes a minute or two of futzing around before it really starts playing. So far, I haven't noticed what I do different to make it start.

Stopping and starting works fine now that I'm playing.

What is the technique I am missing?

Yep. I always undock it. Then I take it to work, and then I sometimes get it playing right away, sometimes it takes a bunch of pressing.

My iPod is new, and I am still updating it often. I suspect the problem is with my finger technique.