Hello Narkissos - As a previous poster said, your topics never fail to make a person think; your topics are invariably thought-provoking.
As for me, I associate freedom with folly, madness, if you will. This idea has its symbolic representation in the idea of the trickster, or of the Fool.
The trickster is usually associated with Native American [i.e., "Indian"] lore, and, of course, the Fool has a long "pedigree" in European literature and folklore. For me, the two figures of the Fool and the trickster represent - in Jungian terms - the archetype of freedom. Throughout native American and European legends, these two figures represent correctives to social control.
I am sure that you have heard of Erasmus' In Praise of Folly, his encomium to madness. And, of course, the Fool appears in the Tarot deck.
There is a book entitled An Open Life, in which are featured a series of conversations between Joseph Campbell and Michael Toms. In the chapter, "Myth as Metaphor," Campbell, in response to a question of Toms concerning the role of the Fool, remarks - "And there's a very special property in the trickster; he always breaks in, just as the unconscious does, to trip up the rational situation. He's both a fool and someone who's beyond the system, And the trickster hero represents all those possibilities of life that your mind hasn't decided it wants to deal with...the fool or trickster represents another whole range of possibilities...
The Fool really became an instructor of kings because he was careless of the king's opinion, careless of the king's power; and the king allowed this because he got wisdom from this uncontrolled source, The Fool is the breakthrough of the absolute into the field of controlled social orders [...]
And at the end of the Tarot cards is the Fool, the one who's gone through all the stages that are represented in that series of cards, and now can wander through the world, careless and fearful of nothing."
In my opinion, the king that Campbell mentions in the above example could be interpreted both literally - that is to say, an specific royal monarchial personage - and figuratively, as a sort of synecdoch, a trope in which the part replaces the whole, In other words, the "king" represents "King Reason." For me, the archetype of the trickster/fool is pure potentiality. And it there, in the realm of potetialities and possibilities, that one finds freedom. It is a realm other than the daily, rational one.
Maybe I have been reading too much of Campbell and Hesse. Maybe I should switch to...I don't know...maybe Sade?
