One of the really fun things I've learned from years of doing this and finally getting the hang of things, is that you should always start off like you don't even have a client. Sometimes I like to pretend the client doesn't exist. Sorry lovely clients, you get better work out of me and you know it, if I ignore you for a tiny bit at the beginning.
I think part of the reason it's good to ignore your client a tiny bit at the beginning is that you're allowed to brainstorm. These doodles are just crazy and silly, but they're going in the right direction. I know that penguin kid in a hat isn't going to do anyone any good but I got to draw him without thinking that at the time.
The key to happiness in everything I do is allowing myself the freedom and room I need to create. I don't ever tell myself something is awful. I let it breathe a little bit and I usually come to the right decisions. Don't beat yourself up if something isn't working. Just put it down and draw something else or take a break. One of the great keys to success in life is breaks... speaking of which, I'll get back to this some other time.