The Arizal brings a proof from the Gemara that the best time to do teshuvah and eradicate our sins is in the thirty days prior to Rosh Hashanah, in the month of Elul. In Berachos (61a), Rabbi Yochanan says, “Achorei ari ve’lo achorei ishah — Go after a lion and not after a woman.” It is better to walk behind a lion and risk being devoured, than to walk behind a woman and chance sinning. If one is devoured by a lion, he will lose his share in This World, but if he sins with a woman, he will lose his share in the World to Come.
The Arizal (brought down in Otzar Chemdas Yamim, Chapter 7) says the mazal, zodiac sign, for the month of Av is an ari, a lion (Leo). The mazal for the month of Elul is a besulah, an unmarried woman (Virgo). The mazal for the month of Tishrei is moznayim, a scale (Libra). The Gemara is instructing us: Go — meaning do teshuvah — after the lion, in the month of Elul, which follows Av, whose mazal is a lion; this is preferable to doing teshuvah after the woman, meaning waiting until after the month of Elul to repent. For that would leave us sorely unprepared for our Heavenly trial on Rosh Hashanah, during the month of Tishrei, when Hashem takes out His scale, the moznaim.
Rabbi Chanina ben Dosa says in Pirkei Avos (3:11), “Kol she’yiras cheto kodemes le’chochmaso chochmaso miskayames, ve’chol she’chochmaso kodemes le’yiras cheto ein chochmaso miskayames — Anyone whose fear of sin precedes his wisdom, his wisdom will endure. And anyone whose wisdom precedes his fear of sin, his wisdom will not endure.”
My father once interpreted this mishnah as an exhortation to prepare and do teshuvah in Elul, well before Rosh Hashanah. The Gemara (Shabbos 117b) refers to blowing the shofar as a “chochmah ve’einah melachah — a skill, rather than hard and Biblically forbidden work,” which should be permitted even on Shabbos (although it is not).
Now let’s reread the mishnah: “Kol she’yiras cheto kodemes le’chochmaso” — Anyone whose fear of sin, and hence his teshuvah, comes before the blowing of the shofar, which is a chochmah; “chochmaso miskayames” — his chochmah endures, and the blowing of the shofar helps change the decree.
“Ve’chol she’chochmaso kodemes le’yiras cheto” — But anyone whose blowing of the shofar is performed before he does teshuvah, for he has not prepared for Rosh Hashanah in advance; “ein chochmaso miskayames” — the shofar blowing will not have any effect.
Do teshuvah now; avoid the holiday rush.
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