Down the Up Staircase by Paul Krugman
Krugman examines the problem of saying that "equal opportunity" ensures social mobility upward:
James Surowiecki makes an important point: if you want a society in which everyone has a decent life, you need to construct a society in which everyone has a decent life not a society in which everyone has a small but equal chance of living the lifestyle of the rich and famous.
Not that were anywhere close to the second condition, anyway the most important factor in whether you can become rich is whether you chose the right parents: Most people are going to end up with socioeconomic status close to where they started. But even if that werent true, those moving up the ladder would be matched by an equal number moving down. Since anyone could find himself or herself downwardly mobile, social mobility arguably actually strengthens the case for a strong safety net.
I think you want to read Surowiecki in the context of people like Eric Cantor, who first chose to celebrate Labor Day by congratulating people who start businesses forgetting about the workers then, more recently, tried to get his fellow Republicans to understand that most people work for other people, and that employees vote too. The point is that even in the best of worlds, only a few people will live out Horatio Alger stories; the quality of our society depends on what happens to everyone else.
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