One of the most fascinating and interesting Halachot that we have on Sukkot is the law of Mitztaer. A person that doesn’t feel comfortable sitting in the Sukkah because it’s raining, it’s too cold or too hot, or there are bugs and mosquitoes is exempt from sitting in the Sukkah. Even more than this, they are not allowed to sit in the sukkah, and if they do, they are called a nitwit.
We don’t find this Halacha in other festivals. A person can’t say that eating matzot on Pesach is ruining their Chag. The Gemara even tells us a story of a Rabbi that drank four cups of wine on Pesach, and had a headache until Shavuot.
Let’s leave this question to the side and address a second question that will ultimately answer the first question: If this is really “Zman Simchateinu”, the season of our rejoicing, is it not a contradiction to eat outside, sleep outside and sit outside, without feeling comfortable in our normal place? We are almost going out on a small gallut. Like a son who asked his father, "Why don’t we say Mah Nishtana on Sukkot?" The father responded that we are used to gallut, so we don’t ask. If it’s like gallut, how can we say it’s the season of our rejoicing?
The answer is that Sukkot teaches us the essence of real joy. Joy doesn’t come from great buildings of brick or stone. It doesn’t come from what we shut out. Joy comes from a roof open to heaven, a door open for guests, and a heart open to thanksgiving. Just like Ben Zoma said that he who is happy is one rejoices in what he has. On Sukkot we sit in huts made of only leaves and exposed to the weather, and yet we rejoice on the internal connection to simcha that is not dependent on material things.
This also explains the first question. HaShem wants us to connect to true joy and not to superficial joy. This is why HaShem tells us to leave all the materialism behind and remember how He protected our forefathers in the desert and showed His love to them by wrapping them with the seven clouds of glory. But, if we are suffering in the Sukkah, then it will be difficult for us to connect to this true Simcha.
The Mitzvah is to remember that how we felt comfortable in the seven clouds of glory, but we can't if we ourselves don’t feel comfortable.The point is that we should be happy, even without materialism, but not to simply remove the materialism and to still suffer.
Have a joyous and hopefully dry Sukkot.
Rabbi Tal