When You're Too Afraid To Even Try
I hear from a lot of artists that they're too afraid to send their portfolio to art directors or enter an art annual or something similiar. If you're one of them, please try to REALISTICALLY imagine the worst possible outcome of giving it a try. When you think about it, the absolute worst that can happen is NOTHING. Art directors are not going to blacklist you, that's ridiculous!
If you try it, you're giving yourself a chance to get the job or possibly some useful feedback. If you don't, the deal is already sealed. Nothing happens. For sure. So you might as well give it a try!