The Torah commands us to be happy on Sukkot. In our prayers we call it the “time of our joy”. But aren’t there many elements of Sukkot that make it feel like a period of sober endeavour?
The answer is not totally transparent. Really, every day in the Jewish year is a day fitting for joy and today suitable for thoughtful introspection.
We are always enjoined to connect with Hashem, whatever the date. The difference appears to be the vehicle one uses. On the high holy days, despite the solemnity are festivals, we are enjoined to have festive meals, wear festive clothes.
On Sukkot, despite the joy, we engage in contemplative activities. The festive meals are eaten in a fragile temporary structure reflecting our own mortality. The Lulav and Etrog, fragrant and pleasing to the eye, are taken but signposting the need to accommodate the diversity of human nature. On this Shabbat, which is the happiest Shabbat in the whole year, we read the Haphtarah of Gog and Magog, which speaks at the end of days and read the one of most sobering books of the Bible, the Megillah of Ecclesiastes.
My understanding is that every day contains elements of joy as well as contemplative introspection. Some days we use the vehicle of joy to connect with Hashem; others of contemplative introspection.
Hashem has given us the festival of Sukkot so we can engage with him; using joy fettered with an element of reflection. Rosh Hashanah and Yom Kippur are the festivals provided to connect to Him using pensiveness ameliorated by happiness. Who needs Sigmund Freud?