I call it the Inside/Outside problem.
I first heard about this in relation to Hollywood. Apparently in LA, the most common talk among screenwriters is about how it's nearly impossible to sell a script nowadays. That's all the screenwriters do, all day long - sit around and bitch about how none of the producers are buying.
Meanwhile, what are the producers doing? Sitting around bitching about how it's impossible to find decent material.
I think the same problem applies throughout advertising too.
For example, when you're a young Creative, outside the industry but trying to get in, your perspective is roughly: "Oh my God, there are so many people trying to get in, and so few openings, it's impossible to get a job!"
But when you're a Creative Director, inside the industry looking out, your perspective is roughly: "Oh my God, there are so few talented young Creatives out there, it's impossible to find a good one!"
Similarly for becoming a CD. You're sitting there thinking how hard it is to get a CD job. Meanwhile, the CEO's are all bemoaning how hard it is to find a great CD.
I don't know what the answer is, folks.
I'm just bringing you the problem.