I would say, paradigm shifts are always based on innovation. That can be technological, organizational or in the way we comprehend knowledge. The changes with every innovation are not always positive, but the bottom-line is clear: Innovation provides us with opportunities that haven't been there (think of communication, transportation, capital markets and the scientific knowledge) and it's usually the masses who profit from it the most at the end.
This is why I believe, it won't be a will or desire that will give everyone the most possible degree of freedom, but it is innovation. Will and desire can always and "only" be driving factors for innovational activities (they don't necessarily have to be, usually this is driven by the sheer need or a problem) or the cultural way of integrating a new innovation into the daily life.
Optimizing society to trigger innovations is therefore a key factor for freedom. Unfortunately as the past 200 years have shown, that idea not always follows the path of individualism and freedom.
At the end, the two dimensions of individualism and freedom and innovation and progress have to be kept in balance. I believe true and good leadership should be measured by the degree to which this balance can be kept stable.
Something completely unrelated:
I have seen that you haven't used your votes for witness yet and also haven't set a proxy for your votes. Currently I am working on a project for Steemit called @witness-qr, that aims to collect witness votes by users like you. The plan is to create a transparent rating system for the Steem witnesses and then vote for the most capable ones. I wanted to ask you if you could set witness-qr as proxy. Right now I am still working on the details for the project, but if you like I can give you the (draft of) the whitepaper to read. Thanks a lot!!