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We read Parshas Shoftim in the beginning of Elul because the first step to Tshuva is to put guards at our hotspots. "Shoftim V'Shotrim Tetein Lecha B'Chol She'arecha"; place judges and policemen at all your gates. These gates allude to the gates of your body; your eyes, ears, mouth, etc., says the Bnei Yisaschar. The gemara says the eyes see and the heart desires. This is the mechanics of Aveira. We need to watch both what goes into our mouth and what comes out of it. Once we have honest judges guarding these flashpoints from evil we are on the road to tshuvah.
If we do stumble we must have a mechanism for punishing ourselves whether it is in the form of promising to give money to tzedoka or withholding something that we enjoy for every time we slip. This effective idea was popular among the Talmidim of Rav Moshe Kordevero says the Bnei Yisaschar.
http://revach.net/moadim/elultishrei/ElulParshas-Shoftim-Bnei-Yisaschar-Shoftim-And-Personal-Bodyguards/822
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