I recently heard the following Torah thought, from a local UWS rabbi, to answer the question of why the Sukkot holiday directly follows Rosh Hahsana and Yom Kippur. He quoted a Midrashic source that explains that since there exists the possibility that the Jewish nation was judged unfavorably and deserving of Galut (exile), we take the initiative and place ourselves into exile by leaving our homes and dwelling in the Sukkah, to avoid the real thing.
Let’s analyze this. What is the outcome of exile, besides the obvious physical displacement? There is disorientation, resulting from being cut off from everything that is routine, comfortable, and safe. We are forced to reevaluate, to start over. The self imposed exile that follows the judgment of the High Holidays is an opportunity for us to extract ourselves from the whirlwind of our lives, and reevaluate our goals, relationships, actions, and behaviors. The Sukkah serves as our own personal decompression chamber, from which we can emerge from, and return to our lives, refreshed, reoriented, and re-energized.