Are you free if you are only doing things which are expected of you? No you're not.
To be free you must choose to do things that people do not require you to do. If you are making no such choices, you are not free.
A psychologist had this to say about the importance of choice:
"Behaviour in pursuit of an unrecognised goal, does not feel like a choice" (Larry Crabb).
If you're only doing things because your boss, your teacher, your wife (etc) expects it of you, you are not free; you're a slave.
So does this mean we are trapped by our circumstances? Not at all. The slave who chooses to do things for their master (and or others) that they do not have to do, is freer than the master whose decisions seem forced on him.
When Jesus said, "Anyone who chooses to do the will of God will find out whether my teaching comes from God or whether I speak on my own;" he was referring to the freedom that one discovers when they freely serve others. There's a joy in it that cannot be had in any other way.
"It is for freedom that Christ has set us free." (Gal 5:1)
Jesus came to set us free; to bring the kind of freedom which comes not only from choosing, but choosing that which most satisfies our hearts. (There is no point in having a strong will if you choose that which does not satisfy. Jesus came to make our wills strong and our hearts free.)
Should we do what our boss says or what our teacher says? Yes, if you don't have to go against your conscience. But don't stop there. Do things for them that you do not have to do and you will begin to experience the joy of freedom. Trust Jesus. Only he can set you free.