Our Sages taught that the month of Elul is hinted in the verse, “Ani Le’Dodi Ve’Dodi Li” (“I am to my beloved and my beloved is to me”). “Dodi” refers to Hashem while “Li” refers to the Jewish nation. During the month of Elul, we experience fulfillment of this verse as we are to Hashem and Hashem is to us, which means that there is an extra closeness between Hashem and the Jewish nation during this month.
It is a widely-accepted notion that during the month of Elul, every Jew should be focused on repentance and coming closer to the service of Hashem. Although this is entirely true, we must not forget that Hashem is also bringing Himself closer to us during the month of Elul and during this month when the attribute of mercy is rampant, He is quicker to forgive and accept those who return to Him. Indeed, the Midrash on the above verse states, “Hashem says to the Jewish nation, ‘You are my portion’ and the Jewish nation says to Hashem, ‘Hashem is my portion.’” Indeed, Maran Ha’Chida writes (in his Chomat Anach, Shir Ha’Shirim, Chapter 6): “One must awaken himself towards repentance and this is hinted in the verse ‘I am to my beloved.’ When one does so, then ‘My beloved is to me,’ meaning Hashem will assist him in doing so, as one who comes to purify himself receives Heavenly assistance, especially during this month when there is an abundance of Heavenly mercy.”
A parable to illustrate this point is that once, a bitter fight erupted between two friends. When one friend wishes to appease the other, if he knows that the friend is the type that is hard to forgive, this will make it ever-harder to ask for forgiveness for the individual is concerned that he will be rejected. However, if he knows that the friend also wishes to make amends and is easy to forgive, it is then much easier to approach the friend, ask for forgiveness, and reinstate the previous friendship.
The same applies here. There are those that see the month of Elul as a burden, for we must search deeply into the depths of our souls in order to unearth our iniquities and then arouse ourselves to perform Teshuva. However, precisely the opposite is true in that this month is the time for maximum closeness and love with Hashem. We should be so happy that we are this fortunate that Hashem is willing to accept us as His children.
This is why Hashem says, “Return to me and I shall return to you.” Our Sages taught, “Hashem told the Jewish nation, ‘My children, open up for me even the size of a needle’s head and I will open for you the size of a banquet hall!’” We must accept upon ourselves to repent fully. Nevertheless, we are all aware how far we are from being complete in our service of Hashem. How then can we perform Teshuva? It is for this reason that Hashem asks us to open up for him even a tiny bit, like a needle’s head, as long as that opening remains open forever, in which case there is then hope that Hashem will return us to Him and restore our relationship to the level it was once on.
Hagaon Harav Shalom Schwadron zt”l (famed Maggid of Jerusalem) recounted that once, when he was a young man, his rabbi, Hagaon Harav Leib Chasman zt”l, beckoned him over and suggested that he accepted a new resolution in honor of Rosh Hashanah. His rabbi warned him though that he should make sure that the resolution should be something very small that he felt he would be able to keep forever. Rav Schwadron returned the next day and told his rabbi that he had decided on a small resolution he was certain he would be able to keep. His rabbi told him, “If so, cut that resolution in half and take upon only half of it!”
Sometimes, one understands that one must repent and wishes to accept some sort of resolution upon himself forever. However, not everyone estimates their character and tendencies correctly and then makes the mistake of taking on a “respectable” resolution in order for one to have what to show before Hashem. This is a grave error, for one must know one’s own shortcomings and only accept resolutions that one is certain one can maintain, for any resolutions that are not kept cause tremendous bad. However, smaller, more achievable resolutions have the advantage that one can stick to them and then grow higher and higher every year until one merits completing one’s ultimate Tikkun.