I took a class in college called "social constructionism," that ironically ended up being one of my best experiences there. The theme of the class was that the way we relate to what is normal, real, or essential, is determined by social framing and custom. I say "ironically" because the intention of the professor and the take-away for most of the students was that everything is subjective and relative, and people can't be held responsible by any particular standard.
We watched some of the videos probably everyone with a liberal-arts education has seen - the Stanford Prison Experiment, a security camera showing an unsuspecting subject walk into a crowded elevator to find everyone else facing in one direction away from the door, and other similar footage. We spoke about Einstein's theory of relativity (without any scientific understanding of its content), nature and its laws, scientific classification, and gender and gender roles, among other things.
It struck a chord. Subjectivity and social convention really play a central role in the way we relate to everything in our lives. But for me, I felt that if so much is up for grabs, so much is relative to the framework you abide by, then I'd better choose my framework carefully. I felt relativism was the beginning of free-will, not the end. For example, if my perception of a prison gaurd will automatically influence me to behave in a certain way in that role, I have to decide carefully what that role means to me. If advertising can get me to think something is cool, I have to decide how I will relate to advertising.
Rabbenu Yona, a contemporary of Maimonides, wrote in his famous exposition on repentance, The Gates of Teshuva, that free will is among the higher qualities people can reach in spiritual growth. A puzzling statement, considering that free-will is a basic axiom of all Jewish thought. How can there be reward and punishment for average people if free-will is a special higher quality?
The answer is free-will is also relative. You can be an average person that mostly follows what is socially constructed, except for a small area that is left ambiguous for you to determine for yourself, or you can be a social constructionist and challenge the frames your society has set up.
The way the Torah describes free will is much more than choosing between good and evil. It says "See, I have placed before you life and good, death and evil... Choose life." (Devarim 30, 15-16). Normally we think of "life" as something that just happens to us, not something we choose, and a good life is no more "life" than a bad life. But as usual, the Torah boldy teaches something we would not intuit otherwise. If free-will is about choosing life over death, how could anyone make a bad choice?
Hashem empowered you to choose to be pulled after your natural instincts and social influences, or choose life, base your life on a reality that you have chosen rather than a convention that has happened upon you. That's how its possible to live by the Torah. With free-will, you align your subjective world with a Torah framework. And because Torah "precedes the world" and goes beyond any local paradigms, there's no pulling yourself up by your own bootstraps, and there are levels upon levels, as infinite as anything.