There are two ways to break a window. Either, you can shatter it with a single blow or, you can make a thousand tiny cracks in it. In the end the result is the same. Obedience is similar. Most often, however, we break obedience in those little ways. The large dramatic ones are more rare.
I recognize this all the time in myself and in others. Instead of conforming our will to the will of our superior, our spouse, our boss, or God we often try to duck under it or get around it. There are so many ways to do this that it would just be silly to list them. Plus, I think we all have plenty of personal experience with how we habitually break obedience. But, sometimes we break it without even realizing. An example is when we try to figure out how we can spin a command to align it to my own wants, desires, and needs. But, the virtue of obedience is not to conform the command to me. Rather, it is to conform myself to the command given.
St. Thomas Aquinas has the coolest understanding of obedience that I've come across. It comes from a deep understanding of human nature and a similarly deep understanding of human interactions. He tells us that it is not for the one commanded to pass judgment on the wisdom of the command given. Rather, the one commanded should strive to promptly fulfill the command. However, the one commanded is must determine the time and the place to fulfill the command. Of course, this assumes that the command given is not intrinsically evil.
There is a lot packed into this understanding of obedience. I won't bore you with a complete breakdown. Hopefully, you can see how he beautifully balances human freedom with obedience. What is not clear in this brief statement is the relationship of obedience to God's providence. This is a point that is often forgotten this days. Even in religious life there is a deficit in our understanding of who God's providence interacts with the will of the superior. In my own Order this unity of Divine Providence with the will of the superior was expressed in the formula for written commands. The command would say something like, "it is our will and the will of the Holy Spirit that you ..." Maybe this formula should be restored to help us remember how God fits into things when we receive a command that we don't particularly like. It may helps us remember that we are not to pass judgement on the wisdom of the command given.
There are essentially two reasons why we don't question the wisdom of the command given by the superior. First, we assume the good. Our constant principle for interpreting the actions and words of others must be the principle of charity. We must assume that the one giving the commands is doing his best for everyone concerned. The second reason is because the superior stands in the place of God when he is giving a command. He may not know it. You may not see it. But, God is the master of everything. We can trust that God will work for the good through the commands of someone he has placed over you. This is a scary thought. This means that God has chosen some slob to be the instrument of his will in your life. Well, yeah. But, to some degree we're all slobs. This is, again, why we obey through charity. We assume the good. It sounds naive but it's the right thing to do and its the right way to act. Trust God, trust your superiors, and trust yourself.