Hi Scotty! It's really hard work to make design for yourself! What about me - I try to divide my self - one part - its me as a designer, one part of me -it's customer ! But i do this every time when i make projects for clients too (before i show my first version for client). it's help me find a lot of mistakes before.
Ofcourse it's easier way when you are make design for client - your really know what he or she wants from you.
My logo - I really wanted change it many times. And I asked time to time some people about this. But they almost all adviced me stay it as is. But I still don't sure about this. Maybe I'll do this in future :)