Of course there are ways to fix that. Better education for everyone, and access to upper-middle-class prerogatives like tutoring, clubs, athletics, and unsupervised time with advanced, programmable computers. That's basically the thesis of Gladwell's latest book, that we get mega-successes by providing rich opportunities for young people.
Also, universal and well-funded health insurance is a great way to promote entrepreurial risk-taking. I know so many Americans who are scared to make the leap because they have a member of their family who needs some sort of medical care.
Street sweeping may be an unattractive job for many, which is why it should have a relatively high wage and a good benefits plan.
Actually the fact that you are even suggesting that society needs misery and unhappiness to function... well, this sounds very provocative, but it tells me a lot about your background. It's the sort of thing that is a universal but unstated assumption if you are middle class to elite. The theory is that some, if not most, people are going to have sucky jobs, schools, lives, and opportunities, and this is a good thing, because it motivates people to strive for the "better" jobs. Never mind that this often condemns people to repeat the misfortunes of their parents, no matter how talented they are.
In the USA, people look back on the 50s as some kind of golden era of hard work and conservative values, but that was when there was the least income disparity, the most investment in infrastructure and education (even for adults), and some of the highest tax rates.
Anyway I speak as a guy who went to a fancy private school, but as the token "ethnic" guy whose parents don't go for skiing weekends in foreign countries. So, I've been fortunate enough to see both sides.