In my reading of the early free will debate it became apparent that our modern notion of ‘free’ is quite different from that of the Greek philosophers.
For us the freedom of a ‘free will’ implies an unbounded capacity, the absence of limitations, the ability to pick and choose according to our own desires.
But for earlier thinkers, those who laid the foundations of the ‘free will’ concept, to be free meant to be rational, wise, and virtuous. Free did mean the absence of limitations, but only the kinds of limitations that stop us from acting and being as we ought. The apparent paradox is that wise and virtuous people have no freedom in the modern sense: an honest person is not free to tell a lie. We might even say that virtuous people are ‘enslaved’ by virtue, and the wise have no choice but to act according to wisdom.
The ancient understanding of freedom was built around a normative sense of human potential and human virtue, just as a doctor’s understanding of health is built around a study of the correct functioning of the human organism. ‘Free’ was defined in that context, not in a modern context of existential doubt and an overarching relativism.
Freedom for them was like the free movement of a joint. In a state of health your shoulder should be free to move within its proper range. If you dislocate your shoulder you may be able to extend it beyond its proper range, but this would not be considered ‘free movement’.
Ultimately, this ancient idea of freedom is grounded in an equally deep understanding of what is good for us, such that being free means having an unrestricted opportunity to pursue and enjoy these goods.
It certainly casts a different light on our contemporary sense of freedom and individual autonomy, which is less about the content of our choices and more about our sense of power and sufficiency in the face of obstacles and limitations. The modern idea of freedom and autonomy puts an emphasis on overcoming and avoiding obstacles at a cost to our understanding of wisdom and virtue. It’s why so many people apparently choose to have Sinatra’s “My Way” sung at their funerals. In the end we take comfort not from diligently pursuing something greater than ourselves, but from what is essentially an egoists self-justification set to an uplifting melody.
I think on some level we know that virtue is a kind of limitation, which is probably why we fear it. Not only is virtue difficult to achieve, but it means giving up attitudes and actions that, for most of us, are the substance of our lives. To be free of our attachments and desires is indeed an intimidating thought.