Theologically speaking, freedom and free will have particular connotations in Orthodox thinking that they don’t have in secular culture. Modern Western culture, influenced by the Enlightenment, sees true human freedom as the ability of an individual to shake off the shackles which society imposes on the individual’s thinking. Freedom in popular thinking is defined more as the individual choosing to do whatever that person wants to do. Government, society, law, all become oppressors of the individual as do tradition, culture, social or religious norms. Freedom means freeing oneself from the expectations of others.
Theologically though freedom has more to do with the path we choose in life and the consequences of those decisions. God places before each individual life and all its choices. There is a path that leads to humans being more godlike, and there is a path which leads away from God. We are free to choose the path we will follow, but the paths have very different consequences for ourselves and for all of humanity.
One path, which does follow human choice also means we become more attuned to ourselves as individuals, isolated and alienated from all others. On this path, we lose our belonging to humanity as a whole, we lose our sense of being a relational, interdependent being. We choose our way into a confinement, a slavery to self which ends up being guided by sin. This path seems like the greatest personal freedom but it also involves ever increasingly becoming a slave to self, to sin, to death.

The other path also requires choice, and sometimes is a difficult path, but in it we choose to maintain our relationship with God and with others. It is a path of love which leads to self denial – for the good of the other. We sometimes may feel we are giving up personal freedoms to follow a path of another – of God. But it also is the path which enables us to become most godlike. It involves free choice, but the choice is to limit one’s self interest. It means not making self preservation the greatest good, but to choose to make love for others to be the greatest good.
If we follow the first path we do end up being slaves to self, sin, death and Satan. It may maximize our sense of being freed from the constraint of others. We choose our way to that end. But it does separate us from others and from God, and thus is death. But God who is love willingly provides redemption for those who find themselves in that dead end. No matter how far down that path one may walk, God provides the way out. But, we have to choose to accept God’s offer.
St. Basil the Great writes:
“…let him hear the whole truth of the matter: that every human soul has bowed down under the evil yoke of slavery imposed by the common enemy of all and, being deprived of the very freedom which it received from the Creator, has been led captive through sin. Every captive has need of ransoms for his freedom. Now, neither a brother can ransom his brother, nor can anyone ransom himself, because he who is ransoming must be much better than he who has been overcome and is now a slave. But, actually, no man has the power with respect to God to make atonement for a sinner, since he himself is liable for sin. ‘All have sinned have need of the glory of God. They are justified freely by his grace through the redemption which is in Christ Jesus’ our Lord.‘” (The Fathers of the Church: St. Basil Exegetic Homilies, p. 317)
God’s love for us never ends, even when we choose our way to slavery to sin and death. We will find in that enslavement that we are not free to grow in godliness or to attain eternal life. God provides us a way out of that enslavement to sin and death. We cannot free ourselves of it, but God offers us life if we choose our way back to Him.