Excerpted and Translated from the the Teachings of Rabbi Gershon Steinberg ztz"l
L'ilui Neshamat HaGaon HaTzaddik R' Gershon Avigdor Ben Chaim ztz"l
"May we be at the head."
On Rosh Hashana we say "May we be at the head". In Hebrew, the word for "at the head" is "La'Rosh", which is spelled with the Hebrew letters Lamed, Reish, Aleph, Shin. These are the Roshei Teivot (the initial letters) of the words "La'asot Ratzon Avinu Shebashamayim" (in English: "to do the will of our Father in Heaven").
Why should the Shofar confuse the Satan?
There are those who ask, the Torah was already given 3327 years ago, and every year we blow the Shofar. Therefore, the Satan is already accustomed to the Shofar blasts, so why should that confuse him? The Admor from Satmar explains, that every year there is a decline of the generations, and if so, the Holy One Blessed Be He requests less of us. If so, the Redemption will come, and that is what the Satan is afraid of. Also, there are those who say that the reason that we ask that question is because we don't see Mashiach, but the Satan is an angel and he sees how Mashiach is prepared to come, and because of that he is frightened.
Why do we sing on Yom Kippur "Ashamnu Bagadnu?"
The Tiferet Yisrael at the end of the Tractate of Taanit says, why do we sing on Yom Kippur "Ashamnu Bagadnu..." (in English: "We have been guilty, We have betrayed...")? This is to remind us that sins are able to become Mitzvot if we do Teshuvah (Repentance) out of love. There are those that say that the Satan wants to interfere with the prayers of Israel, but when he comes to the Bait HaKnesset (the synagogue) and sees all kinds of songs and Piyutim (Liturgical Poems) that the congregation of Israel are singing, he thinks that these are not prayers but we are only partying.
Why do we wash our clothing and take haircuts in honor of the Day of Judgment?
In the Shulchan Aruch it is written that we need to show that we trust that the Holy One Blessed Be He will bring our Judgment to light, and therefore we wash our clothing and take haircuts to honor the Day of Judgment.
"Erase in Your Great Mercy the Records of Our Guiltiness."
The words of this phrase in Hebrew are: "Machok B'rachamecha Harabim Shitrai Chovotainu". The first lettters of these words are Mem, Bait, Hey, Shin, and Chet, and those letters together spell the Hebrew word "B'simcha" (in English: "With Happiness"). The trait of Happiness is effective for tearing up an evil decree against us.
Why do we stop blowing the Shofar on Erev Rosh Hashana?
We stop blowing the Shofar on Erev Rosh Hashana (the day before Rosh Hashana). The Magen Avraham wrote two reasons for this: 1) to make a separation between the permissible, optional Shofar blasts during Elul and the mandatory Shofar blasts on Rosh Hashana, and 2) to confuse the Satan so he will think that Rosh Hashana has already passed. The Taz gave a reason, that it is in order to separate between the Shofar blasts that were ordained by the Rabbis and the Shofar blasts of Rosh Hashana, which were ordained by the Torah. The Gr"a in his explanation of the book of Yonah writes that it's possible the reason is that if the Shofar will be blown for 30 days straight, people will become accustomed to the sound of the Shofar and it will no longer arouse them. This is similar to what was found about Titus (in Gittin 26b), that the insect (that was inside his head) after 30 days got used to the sound of the hammer and began again to drill into the brain of Titus. It is written in the Mishna B'rura (section 581 paragraph 24) that even when Rosh Hashana falls on Shabbat, we don't blow the Shofar on Erev Rosh Hashana even though the reason that we need to separate between the the optional and mandatory Shofar blasts no longer holds (since we don't blow on Shabbos anyway). The reason we still don't blow the Shofar on Erev Rosh Hashana in this case is that on Shabbos we say "In memory of the Shofar blast", and it is as if we really did sound the Shofar on Shabbos, especially since in the Temple they did blow the Shofar on Shabbos.
Simanim Tovim (Good Signs)
On Rosh Hashana we eat fruits and vegetables for a Siman Tov (good sign). In the Tractate of Horiot (page 6) it is written that Abaye said that we should be accustomed to see the Simanim (Signs), and in the Tractate of Kritot (page 14) Abaye said that we should be accustomed to eat the Simanim. If someone is worried to eat one of the Simanim, such as Rubia (black-eyed beans) which might be suspected to have insects in it, or if he doesn''t like one of the Simanim, it's possible to bring them to the table and just to look at them, and to say the "Yehi Ratzon" (in English: "May it be the will [of our Father in Heaven]...").
"May it be the will [of our Father in Heaven] that our merits will increase."
When we eat the Rimon (in English: the Pomegranate) we say "May it be the will [of our Father in Heaven] that our merits will increase". It has been asked, how can we stand immediately before the judgment and say that our merits will increase? How is it possible in a short time that we will have lots of merits? The explanation is that when someone who does Teshuvah (repentance) out of love, his intentional sins are changed into merits, and also his bad thoughts are changed into good thoughts. Therefore, we are requesting from Hashem to give us a heart to arouse ourselves to do Teshuva (repentance) out of love, and then we will have lots of merits, and that is why we say "so that our merits will increase".
Be careful to avoid anger.
One must be very careful not be be in a state of anger on these days, because that is the opposite of the Simanim Tovim (Good Signs). (from the Mishna B'rura)
Events that happened on Rosh Hashana.
On Rosh Hashana Yosef came out of prison, and on Rosh Hashana the slavery ended in Egypt, and on Rosh Hashana Sara, Rachel, and Chana were appointed (to have children).
"There is no forgetfulness before Your Glorious Throne."
Someone came to a Tzaddik (a Righteous Man) and said that he suffers from forgetfulness. The Tzaddik answered it is written "there is no forgetfulness before Your Glorious Throne". Repentance is great because it reaches until the Throne of Glory, so the closer you get to Hashem, the less forgetfullness you will have.
"Today the world was conceived."
It is written: "Today the world was conceived". The explanation is that on Rosh Hashana Adam HaRishon, the first man, was formed, because the world itself was created on the 25th of Elul. And why isn't it written "Today was when the world was conceived [in the past]"? It is because the world was only conceived today -- every year the creation is renewed.
"Today the world was conceived."
The explanation is that on this day Adam HaRishon was formed, because on the 25th of Elul the world was created. It has been asked, if so, why don't we say that today Man was formed? The explanation is that just as a woman who has conceived doesn't know what the future child will be -- righteous or wicked, strong or weak, also on Rosh Hashana we still don't know what will be the judgment.
"The remembrance of all the forgotten things comes before You."
It is written: "The remembrance of all the forgotten things comes before You." Those Mitzvot that a man does and he doesn't think about the fact that he's done a Mitzvah and he forgets about it, those very Mitzvot are cherished by Hashem because the person didn't regard himself with pride and conceit.
"Remember us for Life...for Your Sake, Oh Living Elokim."
We request spiritual life, and that's why we sake "for Your Sake, Elokim", that our lives should be for the Glory of Hashem.
Why is the Day of Judgment before Yom Kippur (the Day of Atonement)?
It is asked, "Why is the Day of Judgment before Yom Kippur?" Wouldn't it have been more suitable to clean ourselves of sin on Yom Kippur, and afterwards to come to the Day of Judgment already cleansed? The explanation is, that on Yom Kippur we need to do Teshuva (to Repent) and the Day of Judgment and the 10 Days of Teshuva (Repentance) we arouse the heart to repentance, and Yom Kippur atones.
The Hebrew Letters of the Word Teshuva (Repentance):
The Hebrew letters of the word Teshuva are: Tav, Shin, Vuv, Bait, and Hey. These letters are the initial letters of verses from the Tanach as follows:
Tav - "Tamim Tihyeh Im Hashem Elokecha." (Devorim 18:13). In English: "You shall be wholehearted with Hashem Elokecha."
Shin - "Shiviti Hashem L'negdi Tamid." (Tehillim 16:8) In English: "I have placed Hashem before me always."
Vuv - "V'ahavta L'rayecha Camocha." (Vayikra 19:18) In English: "You shall love your fellow as yourself."
Bait - "B'chol Derachecha Dayaihu." (Mishlei 3:6) In English: "In all your ways, know Him (i.e., know Hashem)."
Hey - "Hetznaya Lechet Im Elokecha." (Micha 6:8) In English: "Walk modestly with Elokecha."
The Ten Reasons for the Sounding of the Shofar:
The Tzaddik R' Avraham Bardaki would quickly learn the ten reasons given by Rabbeinu Saadia Gaon for why we blow the Shofar on Rosh Hashana. Briefly these are:
1) It is because today is the beginning of the creation and the coronation of the Holy One Blessed Be He.
2) Today is the first day of the Ten Days of Teshuva, so it's to remind us that the time of repentance has arrrived.
3) It is to remind us of our standing at Mount Sinai, since the Shofar was sounded at that time.
4) It is to remind us of the words of our Prophets, which are compared to the sounds of the Shofar.
5) It is to remind us of the destruction of the Temple, when our enemies were blowing Shofar blasts to announce their victory.
6) It is to remind us about the Great Day of Judgment in the Future to Come.
7) It's to recollect the Akeidat Yitzchak, the binding of Yitzchak.
8) It's because the Shofar's sound causes us to tremble and to become awakened.
9) It's to remind us about the ingathering of the lost ones of Israel.
10) It's to remind us of Techiat HaMaitim, the resuscitation of the dead.
"May I sit in the House of Hashem all the days of my life" (Tehillim 27:4)
The Torah Reading on the First Day of Rosh Hashana: "VaHashem Pakad Et Sara". 5 men are called up to the Torah. Maftir: The Torah Portion of Pinchas "Uvachodesh HaSh'vii".Haftora: "Vayehi Ish Achad Min HaRamatayim"
The Torah Reading on the Second Day of Rosh Hashana: The Torah Portion about the Akeida. 5 men are called up to the Torah. Maftir: The Torah Portion of Pinchas "Uvachodesh HaSh'vii".Haftora: "Ko Amar Hashem Matza Chain Bamidbar".
May the old year and its curses end; May the new year and its blessings begin.
May you be written and sealed for a Good Year.
Roshei Teivot for 5776:
The new year is 5776, and in Hebrew the letters representing that year are Tav Shin Ayin Vuv.
These letters form the Roshei Teivot (initial lettters) of the phrase "T'hay Sh'nat Oz V'Chedva".(In English: "May This Be a Year of Strength and Pleasure".) These letters also form the Roshei Teivot (initial letters) of the phrase "T'hay Sh'nat Osher V'Kavod". (In English: "May This Be a Year of Wealth and Honor".)