However, there are millions of people in the US, and billions around the world, who work their guts out all their lives, for absolute crap - if they're lucky! Should they be content with their station in life, since they didn't show enough initiative and drive to get out of their poverty?

This is kind of a trick question. Initiative and drive are often paired with discontent with one's situation.

For most people in the world, all the initiative in the world won't help you unless you live under a political and economic system that allows you to do something with it, and to keep the results of your efforts. This is the main problem right now.

In any case, the lack of initiative and drive does not give a poor person a license to loot those who do have initiative and drive, which some people see as the solution.