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Yom Kippur and Sukkot are connected in many ways.  The most simple and obvious connection is the fact that Sukkot follows Yom Kippur. This makes it the holiday on which each Jew takes a few days to celebrate after a month and ten days of utter seriousness, when he or she literally prayed for his or her life.  However, there is also a much deeper connection between these to holidays.

This year, Rabbi Blackstein took the time to illustrate the connection between Sukkot and Yom Kippur through a very significant question.  Kohelet seems to be a very sad and scolding megillah, so why is it read on the happy and joyous occasion of Sukkot?  Wouldn’t Yom Kippur seem like a more appropriate time to read it?  In fact, in his opening comment on Kohelet, Rashi says that the definition of “Divrei,” the first word in Kohelet, is “Divrai Tochacha,” words of rebuke! Would it not make more sense to read it on a day when we are constantly reminded to do Teshuva and follow the right path?  I personally brought along a Sefer Kohelet to shul on Yom Kippur to read, as it gave me a better understanding of what the seriousness of the day had to teach me. 

Obviously, there is some connection between Sukkot and Kohelet, as all holidays have connections to their readings.  Perhaps the connection here is that even though Sukkot is a time of Joy, it also has to be elevated into days of understanding what Yom Kippur was about and why you just did Teshuva.  These are days when we have just been pardoned for our sins, but now we must strive to become better people. 

In his Chumash class last year, Rabbi Jachter raised a question as to why the Torah gives two sets of borders for Eretz Yisrael. The noticeably larger one is from the Nile to the Euphrates, while the smaller one is just from Shevet Dan to Be’er Sheva.  The Jewish people received the smaller Nachalah just for being Jews and accepting Hashem’s Torah, but why must Hashem include another border and what is its significance? The answer is that we, as good Torah Jews, should always be striving for the better. Only once we have reached our higher goals and reached complete purity will we attain that extra Nachalah that Hashem described for us.

If we make a mistake we should not jump to conclusions of “he did it, it definitely was not me” but rather “I made a mistake how can I correct it”.  I’m not sure how many Rabbis who have finished Shas have said, “That’s it, I’m done with learning because I am complete”.  As we see, not even Moshe was complete (he was not given eretz yisrael because even he sinned) but yet, we say every day in Yigdal, “Lo Kam Biyisrael Kimoshe Od.”  We should all set the highest expectations for ourselves.  How we go about reaching those expectations are our own business.  

Walt Disney once said, “If you can dream it, you can do it and it’s kinda fun to do the impossible.”  Indeed, many people may look at their current situation in life and say, “It’s an unfixable and impossible situation to be in and I cannot do anything about it.”  However, this is the message that Kohelet is trying to relay to you.  You’ve just capped off another year on a clean slate.  Now, don’t take Sukkot to be only a time of endless happiness, but take some time to reevaluate yourself.  This is the time to set your goals for the year and to change what you want to change because if you want to do or change something, you, and only you has the power to do so for yourself.  I wish everyone a happy Sukkot and hope that as we read the cryptic Sefer Kohelet it is a little more meaningful and enjoyable to each and every one of us as we strive for our goals.