While it is indeed important to improve yourself and move upward in life - as far as you can - it is unrealistic to expect that everyone can become a CEO or billionaire, or President, or whatever. Our society - indeed any society - functions not because of the people at the top of the pyramid (make creepy triangle sign with hands) but because of all the people in the intermediate levels, including the bottom.
In Robert Heinlein's short story, The Roads Must Roll, he describes a future where "road cities" linked by conveyor-belt-like roads would tie together major metropolitan areas. He got the general idea right, but the details wrong. Washington, Baltimore, New York, and Boston, are almost connected into one mega-city on the East coast, connected by ordinary roads that don't roll, but the cars that do.
The point of the story is about a revolt by the "working men" who believe that they should be in charge, and one man in particular who decides to call a strike and try to take over the roads. The story is interesting because it is not so much about science and technology and futurism, but instead about labor and management and psychology of men. And it illustrates how a few malcontents can really screw things up when they think "they should be in charge" of things.
The reality is, of course, that for every person "in charge" or on top of the pyramid, there has to be two or three or four below him, and a corresponding number below that. For every Mr. Burns, there has to be a Smithers, for Batman, a Robin. You ask yourself, what is in it for them? To be second-string to be big guy - or even further below the food chain. Do they find satisfaction in reflected glory? Or do they realize they are not cut out for the top job?
Now, you can take this one of two ways - as an excuse for failure or an excuse for not even trying, but also as a realization that no matter how hard you try, odds are, you are not going to climb this "hierarchy" (make creepy triangle sign with hands) very far. But you can climb higher than you are, if you try. And even a modest success can be worthwhile, if it means you live a happy, interesting, loving, healthy, and comfortable life.
Dream no small dreams, it is said. But then again, don't be disappointed when your dreams don't quite work out as you thought they would. Odds, are, where you end up might be a different place, but a pleasant place, nevertheless.