It is brought in Halichos Shlomo that R' Shlomo Zalman Auerbach, ztz"l, would often note that the name Elul indicates the work of this season. The month names are from Bavel, so one needs to look to Aramaic to know the origin of the word. In parshas Sh'lach, Moshe sends men to "spy out the land" (BaMidbar 13:2) and the targum of "v'yasuru" (they shall spy) is "vi'allalun"; so Elul actually means to spy and make a clandestine (secretive) investigation.
What was Moshe Rabeinu's intent in sending the spies? Certainly not to see whether or not the land was conquerable; of course it could be conquered, HaShem had promised it! The point of sending in the spies was to find out how best to mount an attack. Find the weak points, get some early successes, establish a foothold, and then proceed to the rest of the land. That's our job in Elul, to spend time spying on ourselves. Where are the weak points in the fortresses of the yeitzer hara? In what areas do we need to be more guarded, because the yeitzer hara is too entrenched for a simple frontal attack? (Our yeitzer hara loves when we make frontal attacks, because we feel like we tried and failed; so we give up.) The preparation we do this month can change our Rosh HaShana and the entire ensuing year. After a month of gathering intelligence we will be like generals meeting with the King; confident that even though we have a difficult campaign, we will have the information and support we need to be victorious.
What was Moshe Rabeinu's intent in sending the spies? Certainly not to see whether or not the land was conquerable; of course it could be conquered, HaShem had promised it! The point of sending in the spies was to find out how best to mount an attack. Find the weak points, get some early successes, establish a foothold, and then proceed to the rest of the land. That's our job in Elul, to spend time spying on ourselves. Where are the weak points in the fortresses of the yeitzer hara? In what areas do we need to be more guarded, because the yeitzer hara is too entrenched for a simple frontal attack? (Our yeitzer hara loves when we make frontal attacks, because we feel like we tried and failed; so we give up.) The preparation we do this month can change our Rosh HaShana and the entire ensuing year. After a month of gathering intelligence we will be like generals meeting with the King; confident that even though we have a difficult campaign, we will have the information and support we need to be victorious.
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