Our parsha starts with several prayers and confessions that we are commanded to say upon the performance of certain mitzvot. One of these is called Viduy Ma’aser, the Confession of the Tithes. In the seven-year Shemittah cycle, every third year we are commanded to go up to the Holy Temple in Jerusalem and “confess” in front of Hashem that we have indeed delivered all our tithes to the Leviim and distributed all our charity to the poor. We then pray to G-d: “Hashkifah M’Meon Kodshecha – Gaze from your holy abode … and bless Your people Israel…”
In Bereshit 18:16 where the Heavenly Angels “gazed” towards the city of Sodom before destroying it, Rashi writes quoting a Midrash: “Any ‘gazing’ that is mentioned in Scripture is for bad, i.e., indicates the detriment of that which is being gazed upon, except for, “Gaze from your holy abode” (Quoted above), for so great is the power of gifts to the poor, that it transforms the Divine attribute of anger into mercy.”
The Divrei Shaul points out a few difficulties with this Midrash that Rashi quotes. Firstly, why is it that the Hebrew word for gazing – Hashkafah – has a negative connotation? After all, you can “gaze” at a beautiful sunset or the shining stars in the sky. So what is it about the word hashkafah that, in Biblical Hebrew, is so negative and to the detriment of that which is being gazed upon?
Secondly, if indeed Hashkafah is to the detriment of the person being looked upon, what is it about tithing and charity that, as the above Midrash indicates, is able to transform that anger and negativity into love and compassion?
To answer these two questions let’s pose a third question (a very Jewish thing to do!). Rabbi Simcha Zissel raises the following contradiction:
In the Shulchan Aruch is written that one should launder his clothing and take a haircut on the day before Rosh HaShanah as a preparation for the holiday. This is based on a Midrash quoted by the Tur which states: “It is common custom for a person awaiting trial to wear dark clothing (i.e. reflecting his state of fear and uncertainty as his very life hangs in the balance), for he does not know if he will be found innocent or guilty. The Jewish people, however, wear white clothing, take haircuts, and eat, drink, and rejoice on Rosh HaShanah, for they know that G-d will perform a miracle for them and judge them with a favorable judgment.”
This seems to contradict which it states in the Gemara: “The ministering angels asked G-d: Why aren’t the Jewish people reciting Hallel (songs of praise) in front of you on Rosh HaShanah and Yom HaKippurim? To which Hashem responded: Is it conceivable that the King is sitting on his Throne of Judgment and the Books of Life and Death are opened in front of him, and the Jewish people are singing Hallel?”
Herein lies the great paradox of the Day of Judgment: Are we supposed to be joyous and eat drink and be merry on Rosh HaShanah, confident that Hashem will find us innocent and will bless us with another good year, or should we be nervous and full of trepidation on this day when the Books of Life and Death are open in front of G-d and we don’t know what awaits us in the coming year? What is the right approach?
Rabbi Simcha Zissel answers that there is no contradiction because there are actually two judgments occurring simultaneously on Rosh HaShanah: the judgment of the yachid (individual) and the judgment of the tzibbur (community). The collective community of the Jewish people is guaranteed a good judgment, for G-d needs us to carry on His mission and to be a light unto the nations. It is the individual who has no such guarantee who has to fear his judgment on Rosh HaShanah.
Rabbi Simcha Zissel adds that the best defense strategy an individual can use in order to guarantee a good judgment for himself for the coming year is to transform himself into a tzibbur. This can be accomplished by taking time out to think about and focus on the needs and challenges of the people around him, mainly his family, as well as friends, co-workers, or even total strangers within the greater Jewish community, and to do whatever he can to help those in need. By becoming “indispensable” to as many people as he can, he is no longer viewed by Hashem as a mere individual but rather as an entire community, since he no longer lives only for himself, but the entire tzibbur needs him. By being needed for others explains Rabbi Simcha Zissel, he will be guaranteed a good judgment on Rosh HaShanah.
We can now return to our original questions. The reason why Hashkafah is always negative is because any time that G-d gazes at a person and judges him as an individual, he is bound to emerge with a guilty verdict, for who can stand up to such intense scrutiny?! However, when a person is careful to give all the required gifts and tithes to the Leviim and the poor – with the understanding that his bountiful crop was given to him by Hashem not just for himself but to share with those in the community who are less fortunate – he transforms himself into a tzibbur and now has the power to transform the Divine attribute of anger into mercy and to be guaranteed the favorable judgment of a tzibbur.
It is for this reason, explains the Divrei Shaul, that the prayer recited upon delivering the tithes (mentioned above) ends with the request: “…and bless Your people Israel”, for it is only as part of the greater community of the Jewish people that the individual is guaranteed blessing from G-d for the coming year.
May we all be able to become needed and indispensable members of the Jewish community, guaranteeing us a favorable judgment this coming Rosh HaShanah.
 See Devarim 26:12-15.
 Devarim 26:15.
 Rosh Hashana 32b.
 Chochma U’Mussar Vol 1, p.20.