Yom Kippur is the climax of the Yamim HaNoraim (more accurately translated as "The Awesome Days" than the traditional "The High Holy Days"). These are days that the mere mention of them is sufficient to awaken one's fear and trembling of Divine judgment. 

 

The mention of E-L-U-L awakens fear of judgment: Rosh Hashana is the day of judgment, and on Yom Kippur the verdict is sealed. This is the sentiment which is felt by most G-d fearing people.

 

However, the Mishna in Taanit describes the experience of Yom HaKippurim in a completely opposite way:

 

"Rabban Shimon ben Gamliel said: Israel never had such good days as the fifteenth of Av and Yom HaKippurim. On these days, the maidens of Jerusalem went out in borrowed white dresses in order to not embarrass those who did not have (appropriate) clothing… and they would go out and dance in the vineyards."

 

The Gemara explains the intense joy of Yom HaKippurim: "This is understood: Yom HaKippurim, since on this day there is forgiveness and pardon, and this was the day on which the Second Tablets were given."

 

This raises a great question. The Torah says: "And this will be an eternal statute for you: on the seventh month on the tenth of the month you shall afflict your souls… And you will afflict yourselves on the ninth of the month in the evening. From evening to evening you shall desist from doing work on your Sabbatical." So we must ask: how did we make this transition from this (affliction) to Yom Kippur being the most joyful day of the year? 

A similar question arises regarding Succot, where "joy" is a central motif of the holiday, and about which it is said "and you will rejoice in your holiday… and you will be only joyful." And additionally: 

 

1. The Torah commands us: "And you shall take on the first day the fruit of a glorious tree, the blades of a date tree, the branch of an intertwined tree and the willows of the stream, and you will rejoice before HaShem your Lord seven days." 

 

 

2. And in the prayers we call it "the time of our rejoicing."

 

 

3. Another expression of rejoicing which is unique to the holiday of Succot is "Simchat Beit HaShoevah", about which the Mishnah says: "Anyone who has not seen Simchat Beit HaShoevah has not seen rejoicing in his days." 

 

 

4. And the holiday concludes with "Simchat Torah" which is a day full of rejoicing.

 

The Midrash explains the special joy of Succot as the result of Yom HaKippurim:

 

"And you will rejoice in your holiday (Devarim 16:14): You will find three mentions of rejoicing written about the holiday, and they are: 'And you will rejoice in your holiday' 'And you will be only joyful' 'And you will rejoice before HaShem seven days' (Yavikra 23:40). However, regarding Pesach the subject of rejoicing is not written even once, and why? Because on Pesach the harvest is judged, and one does not know if this year will be a plentiful one or not, and therefore rejoicing is not written regarding Pesach. But regarding the Chag (as Succot if referred to), since the people came out with a favorable judgment on Yom HaKippurim, as it is written: 'Since on this day will atone for (all of) you' (Vayikra 16:30), and furthermore, the grain and the fruit of the trees are already inside (harvested), therefore simcha (rejoicing) is written three times…" 

However, specifically on Succot there is a restriction, more difficult than on other holidays. True, on Pesach it is forbidden to eat chametz, but as the years go by and the abundance increases, this prohibition is becoming less and less restrictive, and today nearly every imaginable type of food is available with high-level Kashrut for Pesach.

 

But on Succot we are required to leave our home and live in a temporary home, which doesn't even protect us from the rain.

If it is so important for the Torah that we will rejoice, why does it not allow us to remain in the situation where we can rejoice in comfort?

How can we reconcile simcha on one hand with the difficulty of achieving this joy when one leaves his home – his fortress?
Let us explain the special joy of Yom Kippur, and from this we will understand the special simcha of Succot. 

The Gemara (Shabbat 11a) discusses the law of ta'anit chalom (a fast after a bad dream):
"And Rabbah bar Machsia said in the name of Rav Hama bar Giora: Rav said: A ta'anit chalom is effective (against a bad dream) just like fire burns dry leaves. Rav Chisda said: on the same day (after the dream), and Rav Yosef said: even on Shabbat."

One who has had a bad dream, which shocks or disturbs him, from the din (letter of the law) he must designate that day as a fast day, even if the dream was on Shabbat.

And the question arises: is it not forbidden to fast on Shabbat?

HaRav Kook writes in Ein Aya"h that one thing which gives a person greater pleasure than eating and drinking is maintaining his spiritual (emotional) balance, whereas a bad dream symbolizes a negative shift in his mental balance, to the direction of base desires. Even more than a person is interested in eating, he desires to cleanse and repair himself. Therefore, in a situation like this, the pleasure is not in eating and drinking but rather in fasting, which restores a person's soul to its equilibrium. 

Similarly, on Yom HaKippurim: indeed fasting is an affliction, but the Gemara says that what interests a person at this point in time is not physical food, but the purity of his soul.

A person's happiness comes not only from eating and drinking, but principally from the spiritual significance of his deeds.
Each holiday builds a level in one's soul, but only Yom Kippur atones for us and purifies us, and this is the height of simcha. So if the price for this is "affliction", this is a price worth paying to gain this great benefit.
According to this we can offer another explanation (one of many) regarding the special simcha of Succot. A man searches for the significance of his deeds, and generally, most of his deeds carry no inherent significance, they are not Mitzvot in themselves, but they are means to ends. However, on Succot, when a Jew is in a Succah, every action which on a regular day is defined as a mundane action - for example sleeping, eating, and conversing – receives the status of a Mitzvah when it is done in the Succah. Therefore it has significance, and this significance is what infuses a man's deeds with joy. 
Viktor Frankl, the famous Jewish psychologist, wrote the book "Man's Search For Meaning" where he explains that what gives man strength and resilience is the significance of his life, and not the fun or difficulty which accompany his life. "He who has a 'why' can bear any 'how'."

The significance of Yom HaKippurim, and the significance of every action in the Succah are what bring joy to these days.

On this Shabbat we will read "Shirat Ha'azinu" and we must look at what kind of shirah there is in this song, for the song contains words of severe rebuke. Apparently, the answer is in the end of the parsha "And (He) will atone His Land (and) His nation." When the nation knows that the ultimate purpose of all its trials and tribulations is to atone for the nation and the Land, that these were not purposeless sufferings but atonement which has significance, then even harsh situations can take on the quality of a 'song'.

The message which emanates from this is that one who seeks happiness should not set his sights upon that which is fun, agreeable or pleasurable and attempt to escape from every difficulty. But rather, one must search for emotional balance, for spiritual tranquility and purity, and principally for the significance of his life – this is the path to a full and joyful life.

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