Shalom,
Today marks Rosh Chodesh Elul (the 1st day of the month of Elul) which means only 1 month till Rosh Hashana (New Year) and the Ten Days of Awe/Trembling...
http://www.torah.org/learning/yomtov/roshhashanah/vol1no35.html
The Month of Elul: Customs
By Rabbi Yehudah Prero
As we mentioned in the last post, the month of Elul is a month set aside for preparing ourselves for the upcoming High Holidays, Rosh HaShana and Yom Kippur. Because of the tone set for this month, there are various customs which we have adopted. These customs, as we will see, have to do with repentance and the upcoming new year.
The Recitation of Selichot - Penitential Prayers
We find that the author of the Shulchan Aruch began the section dealing with the High Holidays (Orech Chayim 581) with the following: "We have a custom to rise before dawn to say penitential prayers and supplications starting from Rosh Chodesh (the beginning of the month of) Elul and continuing until Yom Kippur."
The Rama commented on the above and said that this is not the custom of B'nai Ashkenaz (although it is the custom of Sefardi Jews). Ashkenazi Jews begin saying Selichot the Sunday before Rosh HaShana. However, if Rosh HaShana falls out on either Monday or Tuesday (as it does this year), we start saying Selichot from the Sunday of the week preceding Rosh HaShana.
Why is there a custom to say Selichot, and why begin with Rosh Chodesh? The Mishna B'rura writes that Moshe went up to Mt. Sinai on Rosh Chodesh Elul to receive the second set to Luchos, the tablets upon which the 10 Commandments were inscribed. Moshe then spent the next 40 days on the mountain, returning to the nation on Yom Kippur. The fact that the nation of Israel received this second set demonstrated that G-d had once again found the nation worthy of receiving them, after they had sinned and worshipped the Golden Calf when Moshe went to receive the first set of Tablets. Because Hashem showed favor to the Jewish people then, it is considered a favored time, and one in which our prayers are readily listened to and answered by Hashem. We therefore say Selichot during this time, asking Hashem for forgiveness and to find favor with us, so we can start the new year positively.
Both the Mishna B'rura and the Aruch HaShulchan mention a verse in Shir HaShirim (The Song of Songs) which our sages say alludes to Elul. The first letters of the verse "Ani L'dodi V'dodi Li," "I am to me beloved and my beloved is to me," spell out Elul (Alef, Lamed, Vav, Lamed). The Aruch HaShulchan explains the connection between this verse in Elul as "Now is the time that all my thoughts should be directed towards my Beloved (G-d), and when I do that, my Beloved is also to me, that he helps, assists, and cares for me." The Mishna B'rura explains that this verse also alludes to the time Moshe went up to Mt. Sinai (as mentioned above). This is because the numerical values of the last letter of each word in the verse("Ani L'dodi V'Dodi Li"), when added up, equal 40, the amount of days Moshe spent on the mountain, and the time between Rosh Chodesh Elul and Yom Kippur (Yud[=10]+Yud[=10]+Yud[=10]+Yud[=10] = 40). The verse is alluding to the fact that during these 40 days, repentance is accepted, so that one's heart can be closer to his Beloved (G-d) through repentance, and then one's Beloved (G-d) is closer to the person to accept his repentance out of love. We therefore should take advantage of this time to become closer to Hashem and to repent, which is why we say Selichot.
Blowing the Shofar
The Rama mentioned above also comments that the Ashkenazi Jews have the custom to blow the Shofar daily from the beginning of Elul until Rosh HaShana. The Aruch HaShulchan explains that the sounding of the Shofar is a "virtue" associated with repentance. The sound of the Shofar (as we will see in an upcoming post) inspires repentance, and therefore we sound the Shofar during the month of Elul to arouse ourselves so that we repent. The Aruch HaShulchan also quotes the Pirkei D'Rabi Elazar as to why we sound the Shofar. We mentioned above that Elul coincides with the time period when Moshe returned to Mt. Sinai. The reason the nation of Israel worshipped the Golden Calf the first time Moshe went up to the mountain is (succinctly) because they mistakenly calculated the 40 day period they knew Moshe was going to spend on the mountain. When Moshe did not come down at the appointed time, they "created" a new "leader," the Golden Calf, which became an object of worship. When Moshe went up to the mountain the second time, a Shofar was sounded throughout the encampment, so everyone would know exactly from when to begin counting the 40 days until Moshe's return with the second Tablets. The sounding of the Shofar, therefore, prevented the nation from sinning again. Just as the Shofar was sounded back then during Elul to prevent the people from sinning, so too is the Shofar sounded nowadays during Elul.
Saying the Psalm "L'Dovid" - Psalm 27
The Mishna B'rura writes that we begin saying Psalm 27 with the start of Elul, and continue until Shemini Atzeres. (There are varying customs as to when during prayers it is said, and at which prayers it is said.) The Medrash writes that the first verse of this Psalm "Of David: Hashem is my light and my salvation, whom shall I fear?" alludes to the High Holidays: Hashem is my light on Rosh HaShana, and is my salvation on Yom Kippur. Because of this allusion, we say the psalm in the period before the High Holidays, the month of Elul.
The Mahril writes that once we enter the month of Elul, anytime a person writes a letter to someone, it is incumbent upon the writer to somehow allude to the fact at the beginning of the letter that he wishes and hopes that the person have a good year. Others write that expressing these wishes can be done at the end of the letter as well. The standard blessing is "K'siva V'chasima Tova," literally "A good writing and sealing," meaning that the person should be written, so to speak, in the Book of Life, the Book of Good, and be sealed in that book as well.
Rabbi Richman and Yitzak Rueven discuss this on the latest Temple Talk radio show...