The hardest of the 7 1/2 habits for me is #1. "Begin with the end in mind." I can do it, and I often find it useful to know where I want to end up...but...I love just trying new things to see what happens. It's a way of learning by experience, and it's fun to have surprises.
That said, you can guess that the easiest of the habits for me is #71/2. "Play." I love to play and goof around, maybe that's why I try to surround myself with kids and teens. They're looking to play, too. They must play in order to learn. You take away playing from a child, make him/her sit still with their hands folded in their laps, and you take away their most effective way to learn.
So I'm thinkin' this 27 Things stuff is going to make it easier than ever to learn new technology tricks!