My use of tools is always changing. I'm never quite sure that I've discovered the best way to accomplish some task, and I am quite often rewarded with a revelation. Recently I've changed note-taking tools on my phone, my media synchronisation, my action list program and my news reader. Some of those weren't by choice. I've changed web browsers and operating systems over and over, re-learning things in the process. I've changed programming languages and platforms several times too.
My point is that I am always willing to challenge my own status quo, even for small gains. I think it's a valuable mindset to have, but I would, because it's mine.
Mokalus of Borg
PS - I don't know if you should change something that works just to change it, though.
PPS - I change because there's often better software available, and I just didn't know it.