The toughest challenge is finding a design solution that you, your coworkers, and your client can all agree is right for the audience. If this can be done through collaboration instead of compromise, it can also be the more rewarding experience. Once you get past that wall, trust is gained all around and the rest tends to fall into place.
FYI
Cast Iron Design is now The Office of Ordinary Things. We relocated from Boulder to San Francisco, but otherwise we’re pretty much the same people doing the same things, just a bit more hardcore.