This fact should seemingly arouse our curiosity, for during the holiday of Sukkot a person lives outside his home in a temporary wooden hut, without the luxurious trappings and comforts that he is used to in his home. It would seem much more appropriate that the commandment to be happy would be given concerning the holiday of Passover when a person is sitting in his home like a free man, at his shining and beautiful table with all his festive dishes laid out in front of him.
But let us look deeper. It is a terrible mistake for a person to think that his happiness depends on the pleasures that he acquires over his lifetime. Most people feel that the more wealth and comfort that they accumulate in This World, the happier they will be.
But the truth is exactly the opposite: happiness is a quality of the soul, and it never comes from the ephemeral pleasures of the body. To the contrary, the more a person pursues physical pleasures and tries to fulfill them, the more cravings he has for them and the further away he is from true happiness.
A person’s happiness depends on how close he is to what his soul demands — closeness to the Creator of the world, the source of all happiness. A person who believes and knows that G-d is omnipotent and loves him, also knows that it is the way of a lover to benefit his beloved as much as possible, particularly when the goal of creation itself is to benefit the creations.
Nevertheless, G-d gave to each person his portion and didn’t give him more than that because this is exactly what he needs to fulfill his purpose in the world. It wouldn’t be good for him to receive the tools appropriate for someone else. Even if they seem attractive, they would only be harmful for him.
One who realizes the vacuousness and ephemeralness of This World, feels true joy and hardly gives its pleasures a second thought. He is even repulsed by its empty pleasures and has no interest in them. It can be compared to a person who participated in a competition containing many obstacles and pitfalls to prevent him from finding the way out. How happy is he when he identifies the exit after avoiding all the obstacles and pitfalls.
Our sages describe This World as a corridor leading to the World to Come which is compared to the palace. Whoever spends all his time making sure he is comfortable in the corridor is a fool. Soon he will have to leave it, and will have to face the damage he caused himself by arriving unprepared to the palace because he wasted the time he was supposed to prepare himself by making himself comfortable in the corridor.
This helps us understand another reason why we are commanded to be happy on the holiday. Sukkot is also the time of the ingathering of crops. Why do we have to be commanded to be happy when we gather in our crops after tending them the whole year? Aren’t we naturally happy even without a command?
The reason is because the opposite is true. When a person is satisfied with his material state in This World, he is at greatest risk for not experiencing true happiness. Any happiness that one feels from materialism is false, and actually distances a person from true happiness.
Therefore the Torah commands us specifically on the holiday when we gather in our crops “You shall be happy on your holiday!” Be happy on the holiday with your spiritual achievements and not with your material and physical affairs which don’t fill your soul or give it any intrinsic happiness.
This is what is meant by feeling happiness on the holiday, and being happy with the commandment of sukkah that envelops our entire body and uplifts us to the heavens.
May we merit to always achieve “you shall be only happy.”