Knowledge is Power - G-dly Knowledge is Super Power.
The Rebbe asked the student to look out the window and tell him what he saw.
“I see a child falling and getting up again, falling and getting up again.”
The Rebbe told his Chassid. “The point is not so much that the child falls, because that is natural. The lesson is to see the child stand up one more time, each time he falls.”
“On Yom Kippur, and for that matter every day which is a miniature day of judgment, our hope and prayer is that G-d grant us the ability, to stand up just one more time, every day. Every time we do so and we take another step, we strengthen our muscle and habit to fall less often, and to stay standing for a longer period of time.”
In the book of Nechemia it tells us, the entire congregation who returned back to Israel after the destruction of the first Temple 587 BCE made Sukkot/huts together with Ezra the scribe 458 BCE. They sat in them, and there was an inordinate amount of joy, not seen from the times of Joshua - 1500BCE!
So, for over one thousand years that sukkot was being celebrated, as attested by the prophet, this intensity and degree of festivity and joy was never celebrated before!! How does that figure?
On the path of serving G-d there are those that never break the law, (almost never) and there are those who are learning from their mistakes and constantly re-evaluating and improving their thoughts, speech, and actions. Which of the two has greater value in the eyes of G-d?
The one who always goes along the path of the righteous, never veering off far from the right road has been constantly progressing. The one who has stumbled and failed along the way, has detoured, been delayed, bruised and bumped.
Our sages tell us, “in the place of a returnee, even a great righteous man cannot stand.”
The person who lost to his instincts and temptations tasted the superficiality of a narcissistic lifestyle. Tasted failure and experienced the epiphany of knowing the difference between living a worthwhile life and just living to push time along. This realization and the strength to overcome the old habits makes this person way more understanding, way more stronger, and with way more depth and breadth of knowledge than the person who never failed.
The generation of Joshua was those, of the righteous. They entered into the covenant with G-d on the plains of Moav, and they were motivated by the experience of their own eyes which saw G-dliness, to observe all that was written in the Torah. When they entered the land of Israel, they were on a very high spiritual level.
The returnees back to Jerusalem was after the destruction of the Temple and the pursuant harsh exile of Babylon which was brought upon them as the prophet Jeremiah had warned so many times, because of their failures and rebellion against G-d.
When they finally repented realizing the folly of their ways and returned back to Jerusalem to rebuild the second Temple, their joy was far more richer and deeper because, of all the terrible occurrences that was now behind them, than the generation of Joshua could have ever realized or appreciated.
They saw the bad and were now using all of it as a spring board to start anew all over again. They experienced deep darkness and appreciated the value of light like never before.
That is why they celebrated the Holiday of Sukkot now and at this time with a “tremendous great happiness and joy” in the most powerful and passionate way EVER.
The Holiday of Sukkot comes after the repentance and introspection of Rosh Hashanah and Yom Kippur. That is why the Torah/Bible tells us THREE times to be happy on this holiday. The happiness that is available after one has failed and rehabilitated themselves is by far the greatest, way more than any of the other holidays.
Rabbi Sar Shalom of Belz once said. “I am not able to explain fully the deep understanding for the dancing on Simchat Torah. But one thing, one must know. Any prayers that are not able to ascend (to G-d) throughout the year, will go up on this day, through dancing (and Joy of this Holiday).
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