That’s certainly one way that things might go.
But it’s also possible that something quite different could happen. A generation accustomed to carving out its own private spheres of freedom no matter the external circumstances might ultimately be one that lacks the revolutionary impulse that Gillespie and Welch assume is the natural outgrowth of a “hyper-individualized” culture. This is especially true when it comes to things like military policy and the drug war, where the worst effects of our government’s actions are borne primarily by those in society’s lower echelons: so long as no one takes serious steps toward instituting a draft or arresting a third of our high school students for drug use, you won’t find many people agitating for revolt. And it’s not that easy to start a revolution when you can’t pull away from the X-Box.
The first thing to note is that there are many libertarianisms; and while they often go together, they don’t necessarily. Chuck Baldwin, the Constitution Party candidate and Truther, is broadly a political libertarian, but he is certainly not a cultural libertarian. Cultural libertarianism, like its political sister, risks the same sort of reductionism: as political libertarianism often teeters uncomfortably close to anarchism, so cultural libertarianism leans towards libertinism (which, incidentally, is often confused with libertarianism, and thus leads to irrational hatred of libertarians from many conservative circles, even though they broadly agree on politics). Yet libertinism is a much easier trap to fall into than anarchism. Anarchy requires societal change, while libertinism only requires personal change.
Getting back to Schwenkler, the issue here is involved with the “liberating” force of technology, where we can quite literally enter different, almost entirely free worlds whose limits are dictated by your bandwith. What defines a “libertarian” moment — and more pertinently (and philosophically), is the perception of freedom more important than the actuality of freedom?
Taking this to its natural dystopic end, it implies a world of pink goo and Our Savior Ted. This doesn’t make the concern any less pertinent, though. For what if real political doesn’t result in a person’s sense of freedom or liberty? Conversely, suppose a society of technofiends feels more free in a world of WoW 5 and Call of Duty 12 that bans political parties. Who cares if there’s a federal curfew if no one wants to go out anyways? In fact, taking Schwenkler one step further, you might almost say that cultural libertarianism is hindering the cause of political liberty (or that a virtual liberty is hindering the cause of ‘actual’ liberty — whatever these incomplete terms mean).
Should libertarians be striving towards this latter world, or the former? Viscerally, striving towards a perception of liberty seems wrong, but I can’t quite figure out how to refute it.