Relative vs. Absolute

In a free market economy, businesses that do not succeed go bankrupt. The relative success of businesses is a situation much more reminiscent of a zero-sum game than that of countries competing on a global scale. Or so says Krugman.

If relative success at the nation-level isn't really that important and what really matters is your absolute success, then it is possible for each involved party to improve, even though some will grow faster than others. So what would happen if everyone woke up tomorrow and every country in the world were 30x richer than the US? To follow Krugman's logic, this would ostensibly be good for the US; trade and cooperation with other countries would raise the US's level of prosperity, causing the US to be better off than it is today, even if it is the poorest country in the world.

This is tradeoff between relative and absolute success is also prevalent in animal behavior. Dominance hierarchies are perfect examples of relative success being chosen over absolute success. A hiena in a pack which can kill large prey is able to aquire food for itself, and is consequently better off than it would have been by itself. But at the same time, that one hiena might be the lowest notch on the hiena social totem pole.

If the argument for absolute over relative success holds for nations, does it hold for individuals? Would you really rather make $10,000 and be the poorest person in your country than make $5,000 and be one of the richest? If we were measuring in terms of 'happiness' then you might say yes, but if we measure in dollars it's not so clear. Does this mentality hold true across levels of hierarchy? And if so, what units are best to clarify the relationship?