Finding Joy in All the Right Places
Sukkot, Z'man Simchateynu, the Time of Rejoicing comes on the heels of the most serious and solemn days of the Jewish year. Individuals, together with their community, have prayed, and fasted and atoned and now it is time to rejoice.
But how do we rejoice in a time of adversity? This year, celebrating Sukkot in the midst of a pandemic poses new challenges. Luckily, we aren't the first to experience adversity and our texts have a lot to say about the role of joy and happiness and how we can attain it.

Rejoicing Together
There is a special power of happiness which comes from rejoicing with another, or causing another to rejoice. In light of the following sources we might call it the sacred side of joy.
During Moses's conversation with God at the burning bush, Moses tells God that he would like God to pick someone else to go to Egypt to demand that Pharaoh free the Children of Israel. God is angry with Moses and tells him that his brother, Aaron, will accompany him.
(יב) וְעַתָּ֖ה לֵ֑ךְ וְאָנֹכִי֙ אֶֽהְיֶ֣ה עִם־פִּ֔יךָ וְהוֹרֵיתִ֖יךָ אֲשֶׁ֥ר תְּדַבֵּֽר׃ (יג) וַיֹּ֖אמֶר בִּ֣י אֲדֹנָ֑י שְֽׁלַֽח־נָ֖א בְּיַד־תִּשְׁלָֽח׃ (יד) וַיִּֽחַר־אַ֨ף יְהוָ֜ה בְּמֹשֶׁ֗ה וַיֹּ֙אמֶר֙ הֲלֹ֨א אַהֲרֹ֤ן אָחִ֙יךָ֙ הַלֵּוִ֔י יָדַ֕עְתִּי כִּֽי־דַבֵּ֥ר יְדַבֵּ֖ר ה֑וּא וְגַ֤ם הִנֵּה־הוּא֙ יֹצֵ֣א לִקְרָאתֶ֔ךָ וְרָאֲךָ֖ וְשָׂמַ֥ח בְּלִבּֽוֹ׃
(12) Now go, and I will be with you as you speak and will instruct you what to say.” (13) But he said, “Please, O Lord, make someone else Your agent.” (14) The LORD became angry with Moses, and He said, “There is your brother Aaron the Levite. He, I know, speaks readily. Even now he is setting out to meet you, and he will be happy to see you.
Emotions are not often mentioned in the Torah. Why does it say that Aaron will be happy to see Moses? What are we to learn from this? A midrash in Yalkut Shimoni illustrates the importance of being happy for others and rejoicing with them.
(ח)...אמר ר' שמעון בן יוחאי הלב ששמח בגדולת אחיו ילבש אורים ותומים שנאמר ונתת אל חשן המשפט את האורים ואת התמים והיו על לב אהרן כיון שאמר לו הקב"ה כך קיבל עליו לילך. מיד נגלה הקב"ה על אהרן אמר לו צא לקראת משה אחיך כדי שידע שאתה שמח בדבר זה לכך נאמר לקראת משה המדברה. אילו היה אהרן יודע (כתוב ברמז קמ"ב):
...R’ Shimon bar Yochai said: let the heart which rejoiced at the elevation of its brother wear the urim v’tumim, as it says “You shall place the Urim and the Tummim into the breastplate of judgment so that they will be over Aaron’s heart…” (Shemot 28:30) Once the Holy One said this to Moshe, he accepted it and went. Immediately the Holy One revealed Himself to Aaron and said to him: go out to meet your brother Moshe in order that he know you are happy with this situation. This is why it says “Go toward Moses, to the desert.” (Shemot 4:27)

Lifting the Spirits of Others
The Talmud stresses the importance of lifting the spirits of others in the following text.
Jester Designed by Wannapik
ר' ברוקא חוזאה הוה שכיח בשוקא דבי לפט הוה שכיח אליהו גביה א"ל איכא בהאי שוקא בר עלמא דאתי... אדהכי והכי אתו הנך תרי אתי א"ל הנך נמי בני עלמא דאתי נינהו אזל לגבייהו אמר להו מאי עובדייכו אמרו ליה אינשי בדוחי אנן מבדחינן עציבי אי נמי כי חזינן בי תרי דאית להו תיגרא בהדייהו טרחינן ועבדינן להו שלמא:
§ Rabbi Beroka Ḥoza’a was often found in the market of Bei Lefet, and Elijah the Prophet would often appear to him. Once Rabbi Beroka said to Elijah: Of all the people who come here, is there anyone in this market worthy of the World-to-Come? ...In the meantime, two brothers came to the marketplace. Elijah said to Rabbi Beroka: These two also have a share in the World-to-Come. Rabbi Beroka went over to the men and said to them: What is your occupation? They said to him: We are jesters, and we cheer up the depressed. Alternatively, when we see two people who have a quarrel between them, we strive to make peace. It is said that for this behavior one enjoys the profits of his actions in this world, and yet his reward is not diminished in the World-to-Come.

Seeking God
Seeking God is its own source of endless joy, because there is always more to pursue.
Beginning with a verse from Psalms, the 18th century Torah commentary by David Solomon Eibeschutz, Arvei Nachal, explains why those who seek God find happiness.
(ג) הִֽ֭תְהַלְלוּ בְּשֵׁ֣ם קָדְשׁ֑וֹ יִ֝שְׂמַ֗ח לֵ֤ב ׀ מְבַקְשֵׁ֬י יהוה׃
(3) Exult in His holy name; let all who seek the LORD rejoice.
(יב) תחת אשר לא עבדת את ה' אלהיך בשמחה ובטוב לבב מרוב כל כו'. יבואר על נכון עם דברי הבעל העקרים (מאמר ב פרק ט"ו) וז"ל בקצרה: שיש אל החכם שמחה במה שהוא מרגיש שיש בו משלימות החכמה כו', ושמחה זו עם היותה בעל תכלית בהכרח, כיון שהשגת האדם הוא שהוא בעל תכלית, מ"מ תיתוסף תמיד, לפי שכל מבקש איזה דבר, אם הדבר המבוקש הוא בעל תכלית יכלה הכוסף והשמחה כשישיגנו, אבל אם הדבר הנכסף והמבוקש בבל תכלית אי אפשר שיכלה הכוסף ולא שתפסק ההשגה, ולזה תתמיד השמחה תמיד, ולזה אמר הכתוב (תהילים קה, ג) ישמח לב מבקשי ה', כי להיות הש"י ושלימותו בבל תכלית, כל מבקש ה' אע"פ שישיג מה שישיג לעולם תשאר התשוקה ותתמיד השמחה ותתוסף תמיד כשתתוסף ההשגה.
(12) "Because you would not serve the LORD your God in joy and gladness over the abundance of everything," (Devarim 28:47) This can be properly explained through the words of the Ikarim (2:15), which briefly explained are as follows. The wise have joy in that they feel the have achieved some of the wholeness of wisdom...and though this joy of necessity has some end limitation, since it is the product of human comprehension which is itself limited, nevertheless it grows continually. This is because anyone who seeks something which is of a limited nature, once they achieve it their desire and joy will cease. However, if that which one desires and seeks has no fundamental limit, then the desire and the comprehension will never cease. This is why the joy of the wise is continual and unceasing, as it is written "...let all who seek the LORD rejoice." (Psalms 105:3) In that God and his perfection are limitless all those who seek God, though they will grasp what they do, nonetheless will be left ever desiring. The joy will never cease, increasing as one comprehends ever more.

Rejoicing, Even When it Hurts
Life often presents difficulties and bumps in the road. What is the value of being happy even during the tough times? How does one actually accomplish this?
The great Hassidic teacher, Rebbe Nachman of Breslov, turned rejoicing into a mitzvah in the well-known teaching that is often sung in the sukkah.
מִצְוָה גְּדוֹלָה לִהְיוֹת בְּשִׂמְחָה תָּמִיד, וּלְהִתְגַּבֵּר לְהַרְחִיק הָעַצְבוּת וְהַמָּרָה שְׁחֹרָה בְּכָל כֹּחוֹ.
It is a great mitzvah to always be happy, and to make every effort to determinedly keep depression and gloom at bay.
Rebbe Nachman continued by acknowledging that life is full of gloom and depression. For that very reason, he said that a person must put effort into being happy and bringing happiness into the world.
וְהַכְּלָל, שֶׁצָּרִיךְ לְהַתְגַּבֵּר מְאֹד בְּכָל הַכֹּחוֹת, לִהְיוֹת אַךְ שָׂמֵחַ תָּמִיד. כִּי טֶבַע הָאָדָם – לִמְשֹׁךְ עַצְמוֹ לְמָרָה שְׁחֹרָה וְעַצְבוּת מֵחֲמַת פִּגְעֵי וּמִקְרֵי הַזְּמַן, וְכָל אָדָם מָלֵא יִסּוּרִים, עַל־כֵּן צָרִיךְ לְהַכְרִיחַ אֶת עַצְמוֹ בְּכֹחַ גָּדוֹל לִהְיוֹת בְּשִׂמְחָה תָּמִיד וּלְשַׂמֵּחַ אֶת עַצְמוֹ בְּכָל אֲשֶׁר יוּכַל, וַאֲפִלּוּ בְּמִלֵּי דִּשְׁטוּתָא. אַף שֶׁגַּם לֵב נִשְׁבָּר הוּא טוֹב מְאֹד, עִם כָּל זֶה הוּא רַק בְּאֵיזוֹ שָׁעָה, וְרָאוּי לִקְבֹּעַ לוֹ אֵיזֶה שָׁעָה בַּיּוֹם לְשַׁבֵּר לִבּוֹ וּלְפָרֵשׁ שִׂיחָתוֹ לְפָנָיו יִתְבָּרַךְ, כַּמּוּבָא אֶצְלֵנוּ, אֲבָל כָּל הַיּוֹם כֻּלּוֹ צָרִיךְ לִהְיוֹת בְּשִׂמְחָה. כִּי מִלֵּב נִשְׁבָּר בְּקַל יְכוֹלִין לָבוֹא לְמָרָה שְׁחֹרָה, יוֹתֵר מֵאֲשֶׁר יְכוֹלִין לִכָּשֵׁל עַל־יְדֵי שִׂמְחָה, חַס וְשָׁלוֹם, לָבוֹא לְאֵיזֶה הוֹלֵלוּת, חַס וְשָׁלוֹם, כִּי זֶה קָרוֹב יוֹתֵר לָבוֹא מִלֵּב נִשְׁבָּר לְמָרָה שְׁחֹרָה. עַל־כֵּן צָרִיךְ שֶׁיִּהְיֶה בְּשִׂמְחָה תָּמִיד, רַק בְּשָׁעָה מְיֻחֶדֶת יִהְיֶה לוֹ לֵב נִשְׁבָּר:
2. The rule is that a person has to be very determined and put all his strength into being nothing but happy at all times. For human nature is to draw itself to gloom and depression on account of life’s vicissitudes and misfortunes. And every human being is filled with suffering. Therefore, a person has to exercise great effort in forcing himself to be happy at all times, and to bring himself to joy in any way he can—even with silliness. And though contrition, too, is very good, nevertheless, that is only for a brief period. It is right to set aside for oneself some time in the day for feeling remorse and speaking one’s piece in the presence of the Blessed One, as is brought in our works. But the entire [rest] of the day one needs to be happy. For contrition more easily leads to depression, than erring through joy, God forbid, leads to some sort of frivolity, God forbid. For this is the more likely: that contrition will lead to gloom. One should therefore always be happy, and only at the designated time have a broken heart.

      Putting it all Together