All the festivals in the Jewish calendar are joyous occasions. However, only one is actually described as ‘the time of our joy’ - Sukkos. Why is Sukkos associated with happiness more than any other time of year? To answer this question we must first understand why we celebrate Sukkos at all. In fact this is not as straightforward as it seems, because Sukkos is unlike Pesach and Shavuot in one significant way. On both of these two festivals major events occurred; on Pesach the Jews left Egypt and on Shavuot the Torah was given, whereas there was no single event that happened at the time of year that we celebrate Sukkos. Rather Sukkos is a remembrance of how the Jews lived in huts throughout the forty years that they were in the desert which is why we build sukkos and dwell in them for the duration of the festival. This begs the question - why is this cause for such major festivity?! Moreover, the focus of a festival is normally on Hashem’s greatness such as His power and His kindness - this is not immediately apparent in the fact that the Jewish people dwelled in huts in the desert.
To solve these problems we must first try to imagine what living in a desert must be like. The desert is an extremely inhospitable place - it is unbearably hot in the daytime and freezing in the night. There are often very strong winds which cause devastating sandstorms, and there are dangerous animals such as snakes and scorpions. With this in mind it is hard to understand how simple wooden huts could offer the Jews even the scantest protection from this hostile environment. Indeed this is the key to a genuine understanding of what Sukkot commemorates. The huts did indeed offer almost no protection of the Jews in the desert - so why were they not swiftly obliterated by the perils of the desert? The answer is that Hashem protected them - their physical shelter was a mere façade, ultimately it was very clear to them that their survival in the desert was beyond the laws of nature. We too build huts for the week of Sukkos - The halacho requires that they must be made in a temporary manner with a weak roof which does not fully shelter from the sun and rain. This is to remind us of the fact that all the security that we enjoy throughout the year in our strong homes with sturdy roofs is also really a façade. It is only Hashem that can offer true protection.
It is this awareness that we are constantly being looked after that is the cause of the joy of Sukkos. But why is this joy considered more significant to that of the other holidays to the extent that only Sukkos is called ‘the time of our joy’? It seems that there are two basic types of joy. There is the joy of a one-off event and there is the joy of a more constant kind Pesach and Shavuot represent major events that were cause of great happiness. However, the impact of such events, no matter how momentous, inevitably wears out. Whereas Sukkos represents a happiness of an ongoing kind - there was no particular event that symbolised Sukkos, rather it is a remembrance of how Hashem provided the Jews with long-lasting, consistent protection - this teaches us that He is also constantly doing the same for us. The happiness that comes from Hashem’s constant overseeing is not dependent upon any external events, rather it simply requires an internal recognition that whatever happens is under Hashem’s benevolent supervision.
A key to attaining such an awareness is realizing that whatever a person has is exactly what he needs. This is expressed in the Avos: “Who is rich? He who is happy with his portion.” Each person is allotted a ‘portion’ in life - this entails exactly what is best for him in his situation in life. And this portion is perfectly measured to enable him to achieve his fullest potential. With this recognition one is saved from the feeling that life would be so much better if he had more money, a bigger house, or a nicer car. The very fact that we do not have more, shows that Hashem has deemed that it is better for us that way. We often think that if only we were millionaires then everything in life would be rosy.
Sukkos teaches us that Hashem is constantly overseeing us and providing us with exactly what we need to live a successful life. If we can internalize this idea then we can be begin to understand how wonderful true happiness is.