We seem to have stopped explaining how supply and demand works. Companies have a demand for employees with certain skills. If you can supply those skills, they will pay you. The higher the demand for those skills, the more they pay (IT, medical, many trades). If you have a skill that nobody has a demand for (say, theatre, or russian literature), you're in trouble.
Of course if you have a degree that isn't in demand, there's a way out. Find a way to take the skills you have and turn them into someone that companies want to pay money for. Turn your english degree into a career in copywriting, or your degree in theatre into a career in... something.
Is this somehow Bob's fault for being born into the wrong circumstances? Obviously not. But if the aspirational messages that we provide to all people in society are only true for a privileged few, then the communication of same to a larger mass of people for whom it is not is a form of fraud perpetuated on those least able to detect it.
At the end of the day, free college is not going to solve the problem, and I firmly believe it would make matters worse. With no skin in the game, people will get all manner of ridiculous degrees, and the universities will be more than happy to give them to them.