The central message of Elul and the Ten Days of Repentance is that He is on our side
There are those who approach the Aseres Yemei Teshuvah (the Ten Days of Repentance) as accountants — i.e., as if our principal task is to bring our Divine balance sheet into the black, with our zechuyos (merits) outweighing our avonos (sins), and thereby secure a favorable judgment for the year to come. And indeed, they can find support for that approach in the minhag (custom) brought in halachah to take on certain extra stringencies during this period — such as refraining from non-Jewish bread.
Even a superficial reading of the Rambam (Hilchos Teshuvah 3:1) reinforces such a bookkeeping approach: "Every person has zechuyos and avonos. One whose zechuyos are greater than his avonos is a tzaddik...
In his sefer Teshuvah (Mosaica Press), Rabbi Immanuel Bernstein points to a very different approach to the entirety of Elul, culminating in the Ten Days of Repentance. His starting point is a comparison of two comments by Rashi. At the conclusion of Moshe Rabbeinu's second period of forty days on the Mountain on 29 Av, Rashi writes, "On this day the Holy One, Blessed be He, was reconciled with Israel and told Moshe, 'Carve out for yourself two tablets'" (Rashi to Devarim 9:18).
At the end of the third period of forty days, however, Rashi adds a crucial word: "On that day, the Holy One, Blessed be He, was reconciled with Israel b'simchah, and said to Moshe, 'I have forgiven in accord with your words' " (Ibid). The difference lies in one word — with joy. The goal of forty days from Rosh Chodesh Elul to Yom Kippur is not the avoidance of punishment, but rather the creation of a vibrant, pulsating relationship with Hashem at a time when Hashem draws near to make Himself uniquely accessible to us.
In one of the maamarim of Rav Dovid Cohen, Rosh Yeshivas Chevron, on Rosh Hashanah, I found a hint to the same idea. After beginning with a discussion of the special potential inherent in the days of Elul up until Yom Kippur, Rav Cohen offers a lengthy disquisition on the nature of tefillah (prayer). The connection between the opening paragraph of the maamar and what follows is unclear. Surely, what is incumbent upon us in tefillah applies throughout the entire year.
Rav Cohen defines the primary goal of prayer as the creation of a recognition of absolute dependence upon HaKadosh Baruch Hu, a feeling that without Hashem's help we can achieve nothing. As the Ramchal explains in Derech Hashem, this recognition in Shacharis protects us from over-involvement in worldly affairs:
"[As much as it is necessary for the soul to descend into this world,] it is crucial that the soul not descend further than is appropriate. For the more it gets caught up in matters of this world, the more it distances itself from the ultimate Light. Now, the Creator has prepared an antidote for this concern, namely that first a person should draw close and stand before Him, and ask of Him all his needs, and cast upon Him his lot. This will be the beginning point of all his earthly involvement, so that when he then goes about his endeavors... he will not become overly enmeshed in physicality and earthliness, having preceded them by ascribing all to G-d."
By stressing prayer, as he does, while discussing the forty days from Rosh Chodesh Elul, the Chevron Rosh Yeshivah suggests that the purpose of those days is creating a more intense relationship with Hashem. And the primary means for doing so is through tefillah, literally speaking to Hashem.
That also helps to explain the universal custom of reciting Selichos prior to Rosh Hashanah and through Erev Yom Kippur. Rabbi Bernstein asks: What is the point of asking Hashem to forgive us? Either we have done teshuvah, and we will be forgiven, or we have not, and no amount of imploring will help. He notes further that there is very little in the Selichos that is directly connected to teshuvah, whether in the form of the enumeration of our sins or in expressions of regret and a determination to not repeat our sins.
But the answer to this conundrum is that Selichos are a form of tefillah, and as such are part of developing a relationship with Hashem. And the strength of that relationship is the key to all that follows.
IN SHORT, the first task of forty-day period culminating in Yom Kippur is an entire shift in perspective — the development of a G-d consciousness.
Eventually, there will come a time for the pointillist approach to teshuvah — an assessment of our greatest temptations, of the habits that make us most vulnerable to those temptations, and the development of kabbalos (resolutions) designed to short-circuit those bad habits. We can hardly expect to develop a vibrant, ongoing relationship with Hashem if we are mired in sin.
But that is a secondary step. First must come the entire paradigm shift in thinking. The mashal of the besotted lover — Ani l'dodi v'dodi li — is meant to be taken very seriously. Just as thoughts of the beloved are never far from the consciousness of the besotted lover, so must Hashem be at the forefront of our thoughts. (See Hilchos Teshuvah 10:3.)
That involves, inter alia, trying to imagine a world in which Hashem's reign has been fully realized. So much of the Rosh Hashanah davening points us in that direction. "Uv'chein, tein pachdecha — And so too, Hashem, our G-d, instill Your awe upon all Your works..." "Uv'chein, tein kavod — And so too, O Hashem, grant honor to Your people, praise to those who revere You..." "Uv'chein tzaddikim yiru v'yismachu — And so the righteous will see and be glad...." These are words to be savored and thought about.
And thoughts about a world in which Hashem's presence is manifest lead to others: What would each of us be like if we really lived with an awareness of Hashem's presence, and took seriously the injunction to be kedoshim (holy people) worthy to living in proximity to Him? Chazal tell us that a person would never sin unless the spirit of foolishness entered into him. That means that he somehow "forgot" that Hashem is always present.
It is not enough to recognize that Hashem is always present; the central message of Elul and the Ten Days of Repentance is that He is on our team. He has come down from His throne to make it easier for us to form a relationship with Him.
Both Rav Cohen and Rabbi Bernstein offer hints as to how we can take advantage of the opportunity. In his discussion of tefillah, Rav Cohen cites the opinion of Reb Chaim Brisker that one has not fulfilled his mitzvah of tefillah if he did not have in mind that his davening takes place standing in the presence of the King of Kings. It matters not that other Acharonim argue with Reb Chaim's psak: No one contests that it is the optimal way to daven.
And it is indeed a paradigm shift. From that one recognition, everything else follows — the way we stand; our focus on the words; and, yes, our eagerness to avail ourselves of the opportunity to cast our needs upon Hashem.
The paradigm shift with respect to mitzvos is to view them as gifts from Hashem to allow us to connect to him. The word mitzvah itself is from a root indicating joinder or connection. The negative of that view of mitzvos is an approach to mitzvos as an arbitrary set of obligations, a sort of checklist to be gotten through, so we can get on with what we really want to do.
May we all succeed in flipping our perspective to attain the teshuvah described by the Rambam — the kind of teshuvah capable changing us overnight from distant from Hashem to Jews cleaving to the Shechinah (Rambam, Hilchos Teshuvah 7:7).