Increasingly, though, organizational life is becoming about a world in which the higher-ups play "heads, I win; tails, you lose".

Economics and the market economy, as instantiated, is about a number of things other than the usual platitudes of Pareto efficiency, wealth creation, and "freedom".

I'd realized quite some time back that there's a fundamental relationship between economic and political power, a point driven home by Citizen's United and Lawrence Lessig's work. The inability of Libertarians to understand (or admit) this is the central weakness of their philosophy (not helped much by the exploitation of the American Libertarian and Tea Party movements by the Koch brothers: http://en.wikipedia.org/wiki/Political_activities_of_the_Koc...).

Economics and business are also very much about risk management, reduction, and offset. Business legal structures (literally: LLCs -- limited liability corporations, among other forms) exist to reduce the risks of investors. Which can be a positive, but also a harm to society at large. Niall Ferguson, as much as I find him generally personally repulsive, hammers home this point in his Ascent of Money (see especially "Safe as Houses").

The shift of retirement plans from defined benefit to defined contribution is a handy way of shifting risks from fund managers (generally: employers) to employees. The fact that it's also leading to a general gross underfunding of retirement planning isn't unrelated. The story of the oil and energy industry (themselves really the core economic engines of the past century-plus of growth) are largely a continuous story of violation of free-market assumptions through monopoly, collusion, cartel, government ownership, military and diplomatic interventions, and commodity-markets manipulation (Standard Oil, As-Is agreement, Seven Sisters, OPEC, Saudi/Iranian/Venezualan/Mexican oil companies and others, broadly most 20th century wars but particularly WWI, WWII, Vietnam, Gulf I & II, Arab-Israeli conflicts, Britan's coup against Iranian Mohammad Mosaddegh (and all that's emerged from that)). Read or watch Daniel Yergin's The Prize.

The same risk transfers are seen within organizations -- the front line generally takes risks, management sees rewards (though tenure at top spots in firms has also become increasingly brief).

The economy is also as much about wealth concentration as it is of wealth creation, and moreso during decline. Especially in the absence of a progressive taxation system (or even a fair national lottery). John Michael Greer expands on this nicely:
http://thearchdruidreport.blogspot.com/2011/12/what-peak-oil...

And while I agree with your observation that life as a cog in the corporate machine is increasingly less rewarding (again: see the early economists, including Smith's observations on labor wages and Ricardo's Law of Rent for the mechanics behind this), it's a bit less of a vast conspiracy (though there are conspirers) and more of an inevitable Greek tragedy. Not that you might not be able to wage your own Horatio Alger victory over the short or perhaps even longer term, but the fundamental issue is reduced real growth rates within the economy as a whole, very likely caused by increasing constraints on energy flows, availability, and costs.

And that is a subject largely ignored by orthodox neoclassical economics, but increasingly the focus of heterodox economics. I'm finding thermoeconomics (a/k/a biophysical economics) and ecological economics rather more powerful in explaining past, recent, and likely future economic events than the neoclassical models.
http://en.wikipedia.org/wiki/Thermoeconomics
http://en.wikipedia.org/wiki/Ecological_economics