By HaRav Mordechai Greenberg
Rosh HaYeshiva, Kerem B'Yavneh
"Judges and officers you shall appoint in all your cities." (Devarim 16:18) The simple meaning of this verse is the obligation to appoint judges to rule between man and his friend and to teach G-d's laws and His Torah. However, there is an additional meaning that the Mussar masters talk much about. A person is commanded to be a judge of his own matters and to review himself at all times with discernment; thus, a person judges himself. It is not for naught that this parsha is always read at the beginning of the month of Elul, because the time of judgment is approaching, and therefore a person must place himself before the seat of judgment, before G-d does so on the Day of Judgment. The very fact that a person judges himself and appoints himself a judge is the beginning of the teshuva process.
However, every criticism causes a person discomfort. "My sin is before me always" (Tehillim 51:5) places the person before himself in a negative light. It leads to an attempt to escape and puts the person into depression. Therefore, Teshuva is always viewed as something burdensome, depressing and not natural.
In truth, though, Rav Kook zt"l writes in Orot HaTeshuva (15:9):
The upset thought, which comes through the connection to the depths of teshuva, is the source of joy. The basic nature of teshuva is the contemplation of the greatness of the supreme perfection of Divine spirituality. Through this, the sins stand out very much. "You have set our iniquities before Yourself, our immaturity before the light of your countenance." (Tehillim 90:8) And since we sense, as the sensation of sin is any case comes from the Divine shining on the soul, this idea itself fills with infinite joy and greatness. The delight of happiness increasingly strengthens simultaneous with the submission of the heart, which stands at the level of teshuva.
It is through closeness to G-d a person's sins are highlighted more. The sins depress the person, but the closeness to G-d leads to happiness.
"Teshuva does not come to make life bitter, but rather to make it pleasant." (ibid 16:7) Even though the person is still caught in the mud and does not know how to escape it, nonetheless, the very aspiration to free oneself from sin leads to a sense of satisfaction. Rav Kook further writes:
At the time that [a person] thinks all about the burning thought of full regret for all of his sins, at the time that his soul dotes with love for the beauty of sanctity and perfection, longs for her Lover, Creator ... even though he ponders much how to extricate himself from the mud of the sins, even thought it is not at all clear to him how to repair the entire past, even though the ways of action are not at all paved before him, and they are full of stumbling rocks - however, the desire to be good - this is the spirit of G-d's Gan Eden, which blows in the soul and fills it with unlimited satisfaction, so that even the fire of Gehenom of deep suffering, also turns into a river of pleasure.
In a letter that Rav Kook wrote in the month of Elul to one of his disciple, he writes:
I would like to encourage the diligent, may there be many like them in Israel, and to remind you the basic ideas of the means of preparation that we should be involved in, for our true perfection at the year's end, and to prepare ourselves for the light of the holy days ... the Day of Remembrance (Rosh Hashana), the days of Teshuva, and the holy day Yom Kippur, and the days of happiness, the Festival of Succot and Simchat Torah that are coming upon us for good, G-d willing.
The preparations of the month of Elul come not only to impart trepidation and fear, but instead, from the fear of closeness to G-d to reach joy; from the days of Elul, the days of Teshuva, to reach the peak - Simchat Torah. The Chasidim say that all the days of Elul, Rosh Hashana, Yom Kippur, and Chag Succot are only a preparation for "Ata Hor'eta" of Simchat Torah night.