A student just asked Steve why so many libertarians are pessimistic about the direction of the world, given that he just gave a whole lecture on how the world's getting better. His answer was that political activists tend to overestimate their ability to change the world and are thus disappointed when things don't change. Steve also asserted, and I agree, that the world is currently headed toward more liberty rather than less (even accounting for the war and Patriot Act). Over the medium run and long run, we are much better off.
My own view is that a substantial subset of libertarians are "contrarians." Whatever the "mainstream" view of a topic is, they take the opposite, somehow justifying the way in which their heterodox view of the topic is the "real" libertarian position. I will provide examples if requested. I find this "Libertarian Contrarianism" to be both trememdously annoying and horrifically bad strategy, not to mention frequently wrong about what is and is not "libertarian." I keep meaning to write a long essay on it, but just never seem to find the time.