Elul Ideas

The Sages ordained the blowing the shofar [after morning prayers] from the first of the month [of Elul], as was the case in the desert. That is, if the leaders of the generation seclude themselves from the first of Elul in order to improve (m’shaper) their deeds, like Moses in the desert, then they will ascend and join with the people of their generation. But if not – if they are in the exile of the evil inclination – then, the nation must work for itself.
The High Holiday cantors are the generals of the army, and they should wear armor. If not, however, they cannot be relied upon, and each person must fend for himself.
Tzafnah Paneach, p. 25d

[The days] from Rosh Chodesh Elul until after Yom Kippur, are days of Divine favor [and acceptance.] Even though throughout the entire year the Holy One, blessed is He, accepts the repentance of those who return to Him wholeheartedly, nevertheless, these days are unexcelled and most suitable for repentance, because they are days of mercy and favor. On Rosh Chodesh Elul, Moshe went up Mount Sinai to receive the Second Tablets; he remained there for forty days, and came down on the tenth day of Tishrei when the atonement was completed. From then on these days have been designated as days of Divine favor [and acceptance,] and the tenth day of Tishrei as Yom Kippur [Day of Atonement]. In most communities it is the custom to fast on the day before Rosh Chodesh Elul and to recite the prayers of Yom Kippur Katan [minor Yom Kippur], in order to be spiritually prepared for repentance. If Rosh Chodesh occurs on Shabbos, Yom Kippur Katan is held on the preceding Thursday. The Ari (Rabbi Yitzchak Luria), of blessed memory, wrote, "If he did not lie in ambush but Hashem made it happen, then I will provide …" (Exodus 21:13) The initials of the words [ina le'yado vesamti lecha] form the acronym Elul, to indicate that this month is a favorable time for repentance to be accepted for the sins committed during the entire year. It also alludes to the fact that sins done inadvertently also require repentance during this month. The interpreters of allusions also commented: It is written (Deuteronomy 30:6) "And Hashem your God will circumcise your heart and the heart of your children;" the initials of the words [es levavecho ve'es levav] form the acronym Elul. Also, the initials of Ani ledodi vedodi li, ["I am my Beloved's and my Beloved is mine,"] [Song of Songs 6:3] form the acronym Elul. Also, the initials of Ish lerei'eihu umatanos la'evyonim ["One to another and gifts to the poor"] (Esther 9:22) form the acronym Elul. These acronyms are an allusion to three things: Repentance, Prayer and Charity which must be practiced zealously during this month. "Hashem will circumcise etc." alludes to repentance, "I am my Beloved's etc." alludes to prayer, for prayer is the song of love. "One to another and gifts to the poor," alludes to charity.

Even though the sounding of the shofar on Rosh HaShanah is a decree, it contains an allusion. It is as if [the shofar's call] is saying:
Wake up you sleepy ones from your sleep and you who slumber, arise. Inspect your deeds, repent, remember your Creator. Those who forget the truth in the vanities of time and throughout the entire year, devote their energies to vanity and emptiness which will not benefit or save: Look to your souls. Improve your ways and your deeds and let every one of you abandon his evil path and thoughts.
Accordingly, throughout the entire year, a person should always look at himself as equally balanced between merit and sin and the world as equally balanced between merit and sin. If he performs one sin, he tips his balance and that of the entire world to the side of guilt and brings destruction upon himself.
[On the other hand,] if he performs one mitzvah, he tips his balance and that of the entire world to the side of merit and brings deliverance and salvation to himself and others. This is implied by [Proverbs 10:25] "A righteous man is the foundation of the world," i.e., he who acted righteously, tipped the balance of the entire world to merit and saved it.
For these reasons, it is customary for all of Israel to give profusely to charity, perform many good deeds, and be occupied with mitzvot from Rosh HaShanah until Yom Kippur to a greater extent than during the remainder of the year.
During these ten days, the custom is for everyone to rise [while it is still] night and pray in the synagogues with heart-rending words of supplication until daybreak.