One of the major obstacles to change is that the individual's success is at least as much defined by social construct as direct success with reality. We are social creatures and obviously acceptance by others is one key motivator and measure of success. Further, the distribution of money has as much to do with social norms as natural contribution. This is particularly true when more than 90% of Americans are employees of some kind. The price of equities like stocks and homes can rapidly move up or down, illustrating how volatile markets can be; by constrast, salaries within organizations tend to move very slowly, more illustrative of the glacial speed of bureaucracy than market dynamics.
Consequently, little attention is paid to the efficacy of social constructs themselves; most people are so busy trying to succeed within school or work that they pay little attention to the power of schools to actually transform perception or change minds, or the ability of corporations to create new products, new markets, and value.
One of the challenges of the coming decades will be to transform the role of the individual from one focused on success within a social construct into focus on success of creating and changing social constructs themselves. Just as progress in the last century followed from increasing the portion of work force considered knowledge workers, so will progress in this century follow from increasing the portion of the work force considered entrepreneurs. This suggests that our children will succeed not by putting more energy into conforming to social constructs like existing bureaucracies and corporations but, rather, conforming those social constructs to their own potential.