Like many Jews of a certain era, I was reared on stories of the trepidations of the Yamim Noraim – how entire towns in Europe would be terrroized, how people would walk around in apprehension of the approaching Yom Hadin, how every Jew would spend copious amounts of time reckoning with his or her flaws and foibles, how the Baalei Mussar pounded into their adherents the anguish awaiting the unrepentant sinner and his community. I do not doubt the veracity of those accounts but I can state that I do not see it anymore. It is not only that times have changed.
Rosh Hashana and Yom Kippur in different ways are both construed as festive days – Rosh Hashana as indicated by Nechemia (8:10) and Yom Kippur as the happiest day of the year (Masechet Taanit 26b). Rav Kook’s primary thesis in Orot Hateshuvah was that repentance is supposed to be joyous, not just the outcome of forgiveness but the entire process of repentance. For sure, this was a new idea, and dissented from the more doleful approach of the Baalei Musar. To Rav Kook’s mind, the teshuvah of joy spoke more closely to the hearts of a modern generation. If repentance is not joyful, something is wrong. How so?