Sukkot is a holiday full of contradictions. At the time we celebrate our harvest, we are bidden to leave the comfort of our home and expose ourselves to the elements of nature. Even the two reasons given for sitting in the sukkah are contradictory. According to Rabbi Akiva, the sukkah is meant to replicate the sukkot that the Jews actually resided in as they sojourned in the desert: flimsy huts representing the temporary nature of life on earth. Rabbi Eliezer maintained that our sukkot are meant to represent the "clouds of glory" that guided and directed the Jews as they marched in the desert (Sukkah 11b). He felt that the sukkah represents not weakness, but strength, as the protective hand of G-d is with us.
The four species also seem to have contradictory themes. Here, too, we thank G-d as we celebrate our material blessings. In the midst of Hallel, we shake the lulav as we proclaim "Hodu Lashem, give thanks to G-d, for He is good: His kindness endures forever." However, we also shake the lulav as we cry out, “Anah Hashem hosheah na, please, G-d, save us”. We are no longer thanking G-d and singing to Him, but praying for His help. Hence the two explanations as to why we shake the lulav: “He moves them to and fro to He Whom the four directions are His. He raises and lowers to He Whom the heavens and earth are His”. Thus, we shake at Hodu lashem ki tov. “In the West [Israel], they taught it as follows…He moves to and fro in order to halt harmful winds, he raises and lowers them in order to halt harmful dews" (Sukkah 37b). Thus, we shake at Anah Hashem hosheah na.
The Torah reading for Shabbat Chol Hamoed deals with the aftermath of the sin of the golden calf and the revelation to man of the thirteen attributes of G-d. Moshe asked G-d, "Now, if you are indeed pleased with me, allow me to know your ways" (Shemot 33:13). The Talmud, interpreting Moshe's request, claims that Moshe really wanted to know why the righteous suffer and the wicked prosper. Why is life so unfair? Why the contradiction between action and reaction? G-d answered Moshe, "You cannot see my face... you will see my back" (Shemot 33:20-23). Life is full of contradictions, at least from the finite, human perspective. But looked at from the Divine perspective, with the passage of time, the contradictions fade away. Our job is not to worry about how G-d runs the world, but to emulate His attributes of mercy, kindness, and patience.
While this answer is true from a philosophical perspective, man as an individual must live with inconsistencies and contradictions in the midst of an unfair world. This can be very depressing. Therefore, Kohelet, which is traditionally read on Shabbat Chol Hamoed, begins with the lament of Shlomo Hamelech: “Hevel havalim, vanities of vanities, everything is in vain”.
This depressing message, which appears in various forms throughout Kohelet, contradicts the optimistic and hopeful view of life that is at the centre of Jewish thought. The Talmud tells us that the Sages did not want to include Kohelet in the biblical canon. It was only included due to the last verse, in which Shlomo Hamelech teaches us that “when all is said and done, one must fear G-d and keep His commandments, for this is the essence of man”. We may get upset; life may be harsh and unfair; yet our duty is to continue doing what is right. We will not always understand events as they unfold, but it is axiomatic to our belief system that our mitzvot affect ourselves and those who surround us—even G-d Himself.
Sukkot reflects the reality of life, a life full of contradictions, in which blessings, fear, misfortune and hope often co-exist. May we be blessed to rise above life's contradictions as we strive to see the face of G-d.