I recently found this gem of a video online, a talk from graphic design Aaron Draplin of Draplin Design Co. He talks honestly and openly about what to do, how to do it and where to go in the industry. Quick warning, this video has a little bit of swearing.
You may have heard of Aaron Draplin from the video "Why America is Fucked? (Graphically at Least)." He is a designer with a refreshing honesty about the state of the industry and the difficulties of making a career from a passion. For more information check out the Draplin website at http://www.draplin.com/