There is a classic problem here which is discussed in this http://en.wikipedia.org/wiki/The_Grand_Inquisitor (I win today’s esoteric prize?). “The multitude then is guided through the Church by the few who are strong enough to take on the burden of freedom.”
Most people can’t deal with freewill and prefer to push a button over and over again. That bothers us (the enlightened middle classes) so we try to find ways of ‘liberating’ people but in that process. The systems we use to liberate people then slowly turn into institutions and… oops, we are the bad guys. Basically freedom is not the ‘easy’ option because it requires thought and individual responsibility (as you mention Dave). Of course if the education system can’t encourage individuals to deal with these challenges then what can?