Libertarians agree that government is the root cause of ills of the human society. They also tend to agree that government should be either abolished outright or at the very least drastically reduced in size and scope. Hence, the "what should not be" part of the libertarian thinking is clear-cut and obvious. The "what should be" part is likewise clear — a self-governing society based upon private property rights. What is NOT clear or easy is the "how do we get there" part.
The "how do we get there" problem is primarily twofold. First, tens of millions of people are directly dependent on government for their livelihoods. These include retirees drawing on social security, assorted "public servants," education workers, police, employees of corporations primarily or partially working on government contracts, etc. These people are fully pro-government, although they differ on details; "law and order" types favor public funding for jails and more cops on the beat, while "liberal" types want more spending on education and welfare. Second, even those Americans who are not directly dependent on public spending are used to the status quo and see little need to change it in a fundamental way. Instead, they prefer tweaking on the edges, perhaps lowering a tax here or introducing some marginal legislation there. In addition, this group may feel that while public education in its current form is dysfunctional or, at the very least, imperfect, it can be improved through accountability programs such as No Child Left Behind and/or more public spending.
The first group will not give up their entitlements willingly or easily. Instead, they will fight tooth and nail for what is "rightfully" theirs. Witness the resistance put up by the teachers’ unions against school vouchers proposals. Many libertarians argue that public financing of public schools will offer only marginal improvements over the status quo — as the adage goes, he who pays the fiddler calls the tune. Nevertheless, even such a mild and limited challenge to the government monopoly invokes fierce resistance.
Since human beings are naturally wary of the unknown, the second group is unlikely to support radical upheaval of the existing system. In addition, they may feel that one day they too will have to rely on Social Security, Medicare, and other entitlements for their livelihoods. They may also place their faith in government protection services such as police and the military. Let’s put it bluntly — most people in the United States lead generally good lives, at least in the material sense. Their level of material well-being is the highest in history. Many genuinely believe that this well-being is due to the government, at least partially. As the French say, "le mieux est l’ennemi du bien," i.e. the best is the enemy of good. Why risk your current comfortable life by choosing an uncertain alternative? Or, as Herman said in Pushkin’s Queen of Spades about gambling, I cannot risk the essential by trying to acquire the superfluous.
All this reasoning brings us to an inevitable conclusion — a transition to libertarianism would represent nothing short of a revolution and, in order to embrace libertarianism, the society must feel that the status quo is untenable. In Lenin’s words, a "revolutionary situation" must exist. According to Lenin’s theory of revolutionary situation (“those on top can’t, those on bottom wouldn’t”) three conditions must be present for a revolution to be successful: (1) profound crisis of powers that be ("the tops cannot govern"); and no, possible Democrat victory in 2008 isn’t that (2) unusual hardships suffered by the working people — make it middle class ("the bottoms wouldn’t put up with it anymore") and (3) a sharp spike in social unrest and political involvement by the masses. Needless to say, these conditions are not there. Only desperate people create revolutions and the American middle class isn’t desperate (at least not yet). Before you dismiss Lenin’s theories outright, please bear in mind that he instigated and carried out a successful revolution — he was not an ivory tower theoretician.
Will a revolutionary situation rife for a libertarian revolution ever arise? I don’t have all the answers, but maybe you do! A confluence of aging population, Social security and Medicare crises, ballooning public debt, and a host of other factors may one day make the status quo untenable. Whether it will lead to an emergence of a libertarian society or something else entirely is impossible to predict. What seems obvious is that it will take a long time to develop. So, the question arises — why even bother? Why do people such as Rothbard and Lew Rockwell devoted their lives to the libertarian cause? Why do we even bother reading LRC?
Let’s turn back to Lenin. The revolutionary situation is necessary but not sufficient for the success of a revolution. Also needed is a small but dedicated, cohesive, and well-organized cadre of professional revolutionaries (for Lenin, it was the communist party — the "vanguard of the working class"). Similarly, a libertarian revolution will require a large nucleus of intellectuals and educators who will show the libertarian way out of the "perfect crisis." Absent that nucleus, the libertarian revolution is unlikely to succeed.
(Disclaimer: Lenin worked for a profoundly wrong cause, but it doesn’t mean that everything he did was stupid or useless or unworthy of emulation!)