Whenever I'm asked if the Jewish holidays are coming early or late this year, I promptly answer that they'll be coming on time. And that's partially true. Rosh Hashanah will always arrive on the first day of the Jewish month of Tishrei just as Hanukkah will always begin on the 25th of Kislev.
In Pirkei Avot, the rabbis wrote, “Mitzvah goreret mitzvah, averah goreret averah,” one mitzvah (commandment/good deed) leads to another mitzvah, and one transgression leads to another transgression.
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Although we may think time moves in a linear fashion, Jewish holidays insert themselves in unexpected moments and places, seemingly out-of-sync with our expectations.