The more complex things get, in general, the more people are forced to 'drop out'. The "men not having sex" statistic from my last response is an example of this in action.
However, it happens with societies as well. Toward the end of the Roman Empire, the Empire had to force farmers to stay on their land and keep farming... because everyone wanted to move to the city and live on free hand-outs. Almost half the population lived in the city living on state welfare. The farmers wanted to move there too, because it was a better deal for them to live on welfare than to keep farming and retain only a meager share of their yield. Of course if Rome let them move in, there would've been no one providing food for the as much as 50% of the population living on handouts, and the entire system would've collapsed at once. But the fact remains half the population had "dropped out" of even trying to contribute to society... and many more (all the farmers) very much wished to.
Your choices as things grow more complex seem to be:
Eventually there will reach a point where it's impossible for pretty much anyone to do any better no matter how hard he works. At that point, everyone who's not already sitting pretty with dating/money/whatever will just drop out, as the system loses the last shreds of legitimacy. I don't look forward to that (as it means a whole lot of upheaval... and possibly an end to some things we have today that are quite good).
But. We're not there yet. It is still a system where hard work can pay off.
Not as easily as in earlier generations. The Baby Boomers definitely had it way easier than any of the subsequent generations did. Gen Xers didn't have it quite as good, but better than Millennials have had it. But the system is not so calcified yet that you can't carve out your own slice of success.
You probably will have to work a fair bit harder than you would have 15 or 30 or 45 years ago though.