Someone asked Reb Yisrael Salanter zt'l, "Why do you make Elul into a bear?"
He replied, "You’re right; Elul isn't a bear. Elul is more frightening than a bear. Dovid wasn't afraid of a bear, as it states (Shmuel 1, 17:36) עבדך הכה הדוב גם הארי את גם, 'Your slave has slain even the lion and the bear...'
He wasn't afraid of a bear, but he was afraid of the days of judgment. He said (Tehillim 119:120) יראתי וממשפטיך בשרי מפחדך סמר, 'My flesh bristles from fear of You, and I fear Your judgments.'"
So, Elul isn't a bear. It is far more frightening. The gematriya of וממשפטיך בשרי מפחדך סמר (2090) יראתי is the exact same gematriya as (2090) רבא הושענא ,נעילה ,כפור יום ,השנה ראש ,אלול.
It states (Amos 3:6-8) לא ועם בעיר שופר יתקע אם יראה לא מי שאג אריה ...יחרדו, 'Will a shofar be sounded in the city and the people not tremble? ... A lion has roared; who will not fear?' אריה is roshei teivos for יום ,השנה ראש אלול רבא הושענא ,כיפור, days of teshuvah, representing the fear that we have in these days.
Mochiach can be translated as someone who rebukes others, and it can be translated as "proof." He explained to them that he meant that his life is proof that everything is from Hashem."
Tzaddikim have said, "Even fish in the sea tremble on Shabbos Mevorchim Elul."
Rebbe Yissacher Dov of Belz zy'a would cover himself with blankets from the fifteenth of Av. He explained, "It states in sefarim that even fish tremble at this time of year. Fish don’t know what Elul is all about. Those who learn sefarim and understand what Elul is all about should certainly be afraid."
It is repeated that every year, in Yerushalayim, when the chazan would bench rosh chodesh Elul, women in the ezres nashim would faint from fright. People would shout, "Water! Water!"
In the Rebbe Dovid Biderman zt’l court, the atmosphere of erev Shabbos Mevorchim Elul resembled Erev Yom Kippur. The gabaim would ask each other for mechilah, just like on Erev Yom Kippur.
The Magen Avraham (end of siman א"תקצ) writes, "The Sefer Chasidim (ג"תשס) asks, every day Hakadosh Baruch Hu judges the world, so what is the difference between Rosh Hashanah and the rest of the year? It is because on Rosh Hashanah, the judgment is for what will be in many years, like the seven years of the famine."
Pharaoh dreamt on Rosh Hashanah that there would be a famine for seven years. That Rosh Hashanah was a decree for seven years. This aspect of Rosh Hashanah increases our fear because the decrees that will be determined on Rosh Hashanah can affect our lives for many years afterward.
The Beis Aharon traveled someplace before Rosh Hashanah. He told his gabbai, "Prepare the horses [to travel back]. My hair burns from the pachad of Rosh Hashanah."
The Ben Ish Chai (Vayikra) zt'l tells over that a person once came to a city and told everyone that he was "The Mochiach of Prague." Everyone understood that he was hired in Prague to give mussar drashos and to arouse people to teshuvah, so they invited him to speak in their beis medresh.
As he stood before the community, he told them he wasn’t a baal mussar and didn’t have experience giving drashos in public. When he said that he is the mochiach of Prague, he meant that his life is mochiach, proves that Hashem runs the world. He said, "I was from the wealthiest people in Prague, but I lost all my money. Now I'm a bitter and poor man. I also have many problems. My life is proof that wealth is in Hashem's hands. Hashem gives, and Hashem takes, and everything is in His hands."
We tell this story now to remind us that things can change in either direction. The wealthy can become poor, and the poor can become rich. We don't know the future that will be determined on Rosh Hashanah.
A shofar is narrow on one side and wide at the other end. This hints that there are tight, narrow, difficult moments in life, represented by the narrow end of the shofar (המצר מן), and there are good, happy moments in life, represented by the wide end of the shofar (במרחב ענני). Things can change, and we don't know the future. This is part of our fear on these days of judgment.
אריה (which represents Elul and the days of judgment) has the letters that spell ראיה, "to see." We see what happens to people over the year, and this fills our hearts with fear.
Hashem gave us Elul to help sweeten the judgment that everything should be good for us in the coming year. And together with our fear is immense joy. As Reb Mordechai Slonimer zt'l said, "It isn't a band of robbers who will be judging us on Rosh Hashanah. It is our Father in heaven!" We trust that
