By: Rabbi Chaim Yeshaya Freeman
There are different customs regarding when to begin reciting Selichos. The custom among Sephardim is to begin on Rosh Chodesh Elul. The custom among Ashkenazim, however, is to begin on the Motzei Shabbos before Rosh Hashana. The Sephardic custom is based on the idea that we should begin preparing for Rosh Hashana thirty days in advance, similar to the preparation we find before other Yomim Tovim. But what is the reason for the Ashkenazic custom of beginning Selichos only a few days before Rosh Hashana?
The first explanation is found in the Levush (O.C 581:1). He writes that the custom was to fast throughout the Aseres Yemei Teshuva. However, there are four days during this period on which one cannot fast: the two days of Rosh Hashana, Shabbos, and Erev Yom Kippur. Therefore, we begin saying Selichos four days before Rosh Hashana to designate these days as days of fasting and teshuva.
A second explanation is offered by the Eliyah Rabba (O.C 581:8). The Torah's description of the Rosh Hashana offering contains a hint that a person should view himself as though he is bringing himself as an offering before Hashem. Just as an animal designated as a korban requires examination before being brought, we need time to examine ourselves and prepare before appearing before Hashem. The four days of Selichos therefore correspond to the four days of examination required for a korban.
The third approach is found in the Ran (Rosh Hashana 16a). The Gemara explains that Rosh Hashana was established as the Day of Judgment because Adam Harishon was created on that day and was judged after he sinned. The creation of the world began on the twenty-fifth of Elul, while Adam Harishon was created on the first of Tishrei.
Accordingly, the Ran explains that we begin Selichos at least five days before Rosh Hashana because Rosh Hashana takes us back to the very beginning of mankind. Before entering the Day of Judgment, we prepare ourselves by reflecting on the purpose for which Hashem created us and examining whether we are living up to that purpose. Selichos is part of that preparation, helping us correct our ways and return to the mission with which we were created.
The Demesek Eliezer questions why our custom is to begin only four days before Rosh Hashana. He answers that we are actually beginning five days before the second day of Rosh Hashana.
A fourth explanation is found in the Leket Yosher (O.C 118:1). He writes that we need three days of preparation before appearing before the Shechinah, similar to the three days of preparation before Matan Torah. However, these three days must begin after Shabbos, when we are besimcha. Therefore, when Rosh Hashana falls on Tuesday or earlier in the week, we begin Selichos on the previous Motzei Shabbos.
Perhaps we can add another dimension to this idea. The simcha of Shabbos itself can enhance our teshuva. There are two ways to understand this. First, simcha can enable a person to do teshuva from a place of love rather than fear. When a person feels connected to Hashem, his desire to return to Him becomes an expression of that love.
There is also a deeper message in the simcha of Shabbos. Shabbos reminds us that Hashem desires a relationship with us. We are given a day in which we step away from our weekday concerns and dedicate ourselves to Hashem. The happiness of Shabbos comes from recognizing that we are Hashem's people and that He wants us to come closer to Him.
Perhaps this is why Selichos begins specifically after Shabbos. We do not enter the days of teshuva from a place of sadness or despair. We begin from a place of simcha, with the awareness that Hashem wants us to return to Him. The teshuva of these days is not merely about recognizing where we have gone wrong. It is about recognizing that we have a Father who is waiting for us to come home.
Taken from the Kollel Avreichim Hollywood