Question: How should one properly do teshuvah during Elul as we approach the Days of Awe, the Yamim Nora’im?
Answer: The Rambam (Hilchot Talmud Torah 7:13) states, “Even though a sage is permitted to excommunicate a person who offended him, it is not admirable for a sage to react in such a manner. Rather, he should avoid listening to the words of the am ha’aretz, the ignoramus. Let him not pay heed to them, as King Solomon counseled (Ecclesiastes 7:21), ‘Moreover, pay no attention to everything men say lest you hear your own servant disparaging you.’ Such was the way of the pious of the early generations. They would hear others disgracing them and would not answer; and further, they would forgive those who disgraced them and pardon them…. However, this only applies if they were disgraced in private…but a sage who was disgraced in public may not forgive his honor, as it is the honor of the Torah….”
It would take volumes to answer your question comprehensively. Of course, a thorough study of Rambam’s Hilchot Teshuvah is a good place to start.
One thought comes across as a sure key to unlock the door to the gates of repentance: During the month of Elul, we should try to do everything “lifnim mishurat ha’din – above and beyond the requirements of the law.”
Indeed, we find in the Talmud (Berachot 7a) that this trait is greatly valued by Hashem: “R. Yochanan said in the name of R. Yose: How do we know that the Holy One, Blessed be He, says prayers? Because it is written (Isaiah 56:7), ‘I will bring them to My holy mountain and I will gladden them in My house of prayer.’ It does not say the house of ‘their prayer,’ but beit tefillati, lit., ‘the house of My prayer.’ Therefore, we see that the Holy One, Blessed be He, says prayers.’”
The Gemara asks, “What does He pray? R. Zutra b. Tobi said in the name of Rab, ‘May it be My will that My mercy suppress My anger and that My mercy prevails over My other attributes, so that I deal with My children according to the attribute of mercy and, on their behalf, go lifnim mishurat ha’din – stopping short of the limit of strict justice – namely, [acting] mercifully, beyond the letter of the law [in forgiving them their transgressions].’”
The Gemara (infra) tells of a related incident that occurred to the sage R. Yishmael b. Elisha (who was also a Kohen Gadol), who stated as follows: “I once entered the innermost part [of the Sanctuary, the Kodesh HaKodashim,] to offer incense and saw the L-rd of Hosts [lit., the crown of G-d] seated upon a high and exalted throne. He said to me, ‘Yishmael, My son, bless Me.’ I replied, ‘May it be Your will that Your mercy suppress Your anger and that Your mercy prevail over Your other attributes so that You may deal with Your children according to the attribute of mercy and judge them with a mercy that is beyond the requirements of the law.’ And He nodded to me with His head.”
Rashi explains that this nod signified G-d’s assent to R. Yishmael’s words, similar to our answering “Amen” to a blessing.
What we see from this Gemara is the greatness of our relationship with G-d and the unique potential afforded every Jew in his quest for expanding that relationship. The revealing yearning of G-d to solidify His closeness by requesting a blessing from a mere mortal – whether a Kohen Gadol or a scholar, or even both, but nonetheless a mortal of flesh and blood – is a sign of His love for us and, as such, should serve as a sign of the boundless opportunities for closeness with Him as well.
Indeed, we find an open Biblical reference to the heights of closeness to G-d in parshat Shoftim (Deuteronomy 18:14-15): “Ki ha’goyim ha’eleh asher atah yoresh otam el me’onnenim v’el kosmim yishmau ve’atah lo chen natan lecha Hashem Elokecha – For these nations that you are possessing, they hearkened to astrologers and diviners; but as for you, not so has Hashem, your G-d, given for you. Navi mi’kirbecha me’achecha kamoni yakim lecha Hashem, Elokecha, eilav tishma’un – A prophet from your midst, from your brethren, like me, shall Hashem, your G-d, establish for you; to him shall you hearken.”