At the beginning of the Parasha, the pasuk says, (21:10) אויביך על למלמחה תצא כי, "When you will go out to war against your foes." Which war is the pasuk referring to? The Imrei Elimelech of Grodzisk zt'l says this refers to the war of Rosh Hashanah. The Satan prosecutes us on Rosh Hashanah, and we battle him with our tefillos, shofar, and teshuvah. But notice that the pasuk states כי למלחמה תצא, "When you will go out to war." This means the war hasn't begun yet. We are still going out to the battlefield but aren't there yet. The battle didn't start yet. Imrei Elimelech explains that the pasuk refers to Elul. That is when we go out to the war before the war begins. That is the month that we prepare for the great war that will begin on Rosh Hashanah.
He writes, "This pasuk refers to Rosh Hashanah, the day of judgment when people stand before Hashem in judgment. But certainly, on Rosh Hashanah, the day of war, one can't say תצא כי, that he goes out to the war because he is already in the midst of the battle. Rather, the pasuk refers to going out to war before the day of judgment, when we prepare for the war with teshuvah, tefillah, and tzedakah. If we prepare, we will win and be found worthy in the judgment. As the Torah promises בידך אלקיך 'ה ונתנו, Hashem will give us success on the day of judgment [if we prepare for Rosh Hashanah during Elul]."
The final words of the Imrei Elimelech are very important to remember. The days of Judgment are frightening times. Our future is decreed on these days. The Magan Avraham writes that sometimes the decree of what will be for the upcoming several years is determined on Rosh Hashanah. Who isn’t afraid of the great judgment? But if we prepare for these awesome days in Elul (with tefillah, teshuvah, and tzedakah), we can be confident that we will certainly be granted a favorable judgment.
The Dubno Magid's Mashal
The Dubno Magid tells a mashal to illustrate the importance of preparing ourselves for Rosh Hashanah during the month of Elul:
A poor person desperately needed a loan. He came to a wealthy person's home and knocked at the door, nervously thinking about what he would say. He hoped he could convince the wealthy person to lend him money. The secretary answered the door and said that the wealthy person was busy and couldn’t see him then.
The wealthy person had a beautiful garden surrounding his home, so as he waited, the poor man paced around the grounds. An hour later, he returned to the wealthy man's door. Once again, the secretary told him that the wealthy man wasn't available.
The poor fellow nervously paced the grounds some more, waiting for the wealthy man to call him in. When he saw that he wasn't being called in, he tried the door again, but the response was the same. He didn't have time to meet with him.
Finally, the wealthy opened the door and came out of his house. He was going to daven minchah. The poor man rushed over to him and asked for a loan. The wealthy man responded, "Certainly," and he gave him a check for the full amount he needed.
After minchah, another person approached the wealthy person in the beis medresh and asked for a loan. "I am not able to give a loan now," the wealthy man responded.
"But you just gave a large loan to a poor person. Why can you help him and not me?"
The wealthy man replied, "I saw that the poor man really needed the money. He was so worried that he didn't leave my estate all morning. But you happened to meet me at Minchah, so you figured that you might as well ask for a loan. I don't lend money so easily..."
The Dubno Magid explained that this is the concept of Elul. When we daven and prepare ourselves during Elul for the judgment, we show that we are truly worried about it, which will help us receive a favorable judgment.
