The notion of self interest is altered if we think that the biggest human motivation is gathering more personal power rather than struggling towards constant repetition of joyful moments. Current popular understanding of self-interest goes hand in hand with the classically liberal notion of the right to "pursue happiness". That's the idea libertarians use to justify their maximum allowance of freedom of action for individuals. The pursuit towards something psychically warm and cuddly such as happiness seems so right and wholesome for a human being to undertake that denying it seems cruel and out of the question.
Let's look deeper into the supposed utopia proposed with increasing frequency by ideologues like Ron Paul and youthful college educated people around the world who view themselves as having what it takes to become successful capitalists themselves (regardless of the fact that social mobility is constrained in United States as well as in most countries by a small number of oligarch families gaming the system). I don't have any country in mind in this discussion and will use clean abstract concepts ( haha "clean abstract") for simplicity.
For a moment let's forget all the various assumptions and constructs that are needed for libertarian theoretical defense to work at all such as:
1) Free will or what's left of it after a century of Freud, Nietzsche, Marx and now brain scanning experiments
2) Rationality or some common thought process pretending to be rationality in a diverse population with individuals of vastly differing educational backgrounds and consciousness levels
3) Equality before the law as well as rule of law itself for a contractual society to function (laughable fictions in most societies on the planet right now since the most powerful individuals constantly evolve and change the concept of the rule of law through force and brilliant law technologists)
4) Reality. This is a big one in that applying a "perfect" libertarian construct to say, United States is like applying "perfect" proportional representation democratic construct to Afghanistan. Of course the ideologues insist it can work if the whole world united in this purpose and gradually moved towards this workers paradise
My focus however is on self-interest as the driving mechanism in a libertarian society. There is still lack of consensus on what is true human motivation but it increasingly looks that it is a mixture of power seeking as well as pleasure seeking with power being a better explanatory human goal. Many of us have seen the famous quote by Adam Smith,
"It is not from the benevolence of the butcher, the brewer, or the baker that we expect our dinner, but from their regard to their own interest"
At this point many automatically think that being self interested is just wanting to be more happy and that the most important thing to aid our self interest is money. Since desire to make more money is accepted, pursuit of self interest is thus seen as harmless and even sturdy enough to build a radically different socioeconomic system. As mentioned above, there are other takes on what life is all about besides just seeking money fueled happiness. Let's take Nietzsche for example,
"Life itself is essentially appropriation, injury, overpowering of the strange and weaker, suppression, severity, imposition of one's own forms . . "
Since happiness can undertake many forms, the individual thus has a strong case to argue for the right to personally negotiate governance with others and reduce as many regulations on modes/fruits of pursuit as possible. Libertarian ideology then seems the most attractive as individuals become their own utility calculating contractual lawmakers. The result is that the legislative branch in a libertarian society finds itself with little to do. By definition, making laws is creation of uniform regulation on human behavior. This type of government sponsored uniformity becomes redundant (since each citizen is now consenting to enter into contractual regulation of his or her own choice) at best and "coercive oppression" (or any number of silly names given at the GOP protests in recent months) at worst. The libertarian society would then rightfully prevent uniformity from arising and applying to all (unless perhaps dealing with matters that cause grievous harm to others and corporate externalities).
However, if we think of real human motivation as pursuit of influence over their environment (and other human beings within it), allowing humans the maximum playing room begins to take on a more sinister dimension.
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This thriving overlapping regulatory complexity with greatly decentralized nodules of influence (assuming the invisible hand goes against all history and human nature so far and prevents monopoly formation) is a double edged sword. Free market is relatively efficient at distribution of capital (at least on sub-national local level when legal conditions are favorable) and the regulatory contractual patchwork is often better able to adapt to pressures of time and social flux. One thing the invisible hand is less good at is redistribution of justice (giving people what they think they deserve).
At the end of the day in the modern world, justice (in all its current forms) is mostly in the monopolistic hands of the legislative branch. The legislative branch makes it uniform and standard for a time. In this branch, all individual free market actors ( the people) have a say about what uniform sort of justice is right for a particular society. There is of course, indirect influence from larger clusters of power and bigger free market actors (ranging from small businesses to billionaires to churches to transnational corporations) that cannot totally be avoided.Their influence is generally somewhat counterbalanced through sheer numbers of lesser powered individuals and their allies in the powerful agent of the legislative.
A new form of feudalism arises. Whatever people "deserve" in this society is whatever they can wrestle from others through raw financial power (acquired by individuals with personal physiologies that thrive in free market conditions or those who were born into wealth or both). The new creators of standards and norms are thus illegitimate (nobody voted for them unless it is stock owners voting for new company leadership) and they are constrained by nobody but market conditions. Even market conditions can be shaped with strong enough players and enough money. In a legal legislative vacuum, even informed consumers and workers have little bargaining power against the abuses of various cartels, guilds, and land barons (whatever new name they would go under informally or formally). Less powerful individuals would strategically be forced to dedicate substantial amounts of time to collective bargaining. Emergence of powerful unions for service industry is difficult to speculate on but without government protection new forms of protection will have to be devised and vigilantly implemented ( 1> this in turn creates inefficiencies/other abuses as union leaders are as interested in power as CEOs and use up substantial amounts of productive resources on court battles and organization 2> union power receded in part due to rise in service industry and in part because the legislative addressed their concerns through legal regulation)
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This discussion had a medium sized country in mind. If a libertarian country is smaller, one can easily see the whole of society dominated by one or two international corporate actors with the wealth flowing out of the country. A dystopian cyberpunk future in the mold of William Gibson is essentially a libertarian one. The unhealthy corporate influence in America and its corrosive effect on government is due precisely because the strong in the legislative are splintered against each other while the strong in the private sector are gaining through attrition. Having a poorly functioning legislative battling the executive does not stop excesses of power. It just creates dysfunctional weak government. The excesses continue in the private world that permeates the public. Parliamentary government with proportional representation (with constitutional protection) is thus a much better guarantor of decentralization of power within society.
The 21st century cannot afford a disjointed slow self cannibalizing government concocted by 18th century aristocrat intellectuals. Something so out of date is in no position to face a fast paced world or promote freer development of vast majority of individuals against the designs of domestic and foreign elites. It does us disservice to think of power as just residing in government that we should be free from. Better separation of powers would be the strong in private and public spheres balancing each other in a healthy dialogue with the weak being the middlemen between the two.
So emerges perhaps the biggest argument against libertarian designs, that:
1) in a free market world there is insufficient separation of powers and mechanisms to keep them separated
2) this is dangerous in that human motivation is not just about getting happy through making more money (and making trickle down economics work in deranged minds of some propagandists)
3) only democracy through some sort of proportional representation creates enough of a split and balance between power elites by creating a strong legislative branch that can check the feudalistic desires of many oligarchs
The biggest dangers affecting many "civilized" and "developed" nations are thus not too much government but a government that is too weak to stand up against private financial interests. Proportional representation democracy is not perfect of course but it seems like a step forward than backward at the moment for most of the population of any given country.