"The blessing – that you shall listen to the commandments …" (Devarim 11:27). The main blessing is not the external reward that one receives from Hashem but is the listening itself. Fortunate is the person who knows how to feel this, for then his life is like the Garden of Eden. When we make an appraisal of our lives, we will find that most people are not satisfied. Sometimes people think that it is because they are missing this or that, and they aim to obtain it so that they will finally be satisfied. Wonder of wonders – we always find ourselves lacking something, and we always have to toil to obtain it. It is like the edge of the sky in the eyes of a baby. The closer you get to it, the more it seems to be escaping us.
The blessing is to identify the source of blessing, and to realize that we are not at all looking in the right direction. It is easier than we realize to find satisfaction. It is actually in our hands, in what we possess – it is, "that you shall listen."
It is reminiscent of the sorcerer in the story of Ashmedai (Gittin 68a). He searches for his treasure at the edge of the universe and does not realize that he is standing on it. That is what all of us do. We work so hard looking for our treasure, turn our hair white, and ruin our posture so that maybe we will find some satisfaction and happiness. Much of that work is for nothing. You already have the blessing – a daf of gemara, a perek of mishna, Chumash with Rashi. It is not that hard and does not require great exertion.
"The spirit will not be filled" – there is a parable of a simple city dweller who married a princess. If he brings her everything he can find, it will not be important to her, for she is a princess (Kohelet Rabba 6:1). The soul demands its nourishment. Instead, we give it food that it cannot digest because our soul is from above.
The job of the month of Elul is to fulfill the pasuk: "If a shofar will be sounded in the city, will the people not tremble?" (Amos 3:6). In other words, we need to shake the heart out of its complacency. Sometimes one is so sure of himself that he has no doubts about his decisions. Elul is there to loosen the nails we have placed around our path, which convinces us that we are always right and our motivations are always complete. Elul awakens doubt. In that way it is an introduction to the Ten Days of Repentance. It is interesting that the introduction is three times as long as the period of repentance itself. If a person does not realize he can be wrong, he does not realize he can sin, and then there can be no repentance. If we remove the wall of self-reliance, we will see the ugly truth … and we will realize for what we need to repent.