The story is told regarding an interesting conversation which occurred between the Greek philosopher Plato and lehavdil elef havdolos, the prophet Yirmiyahu after the destruction of the Bais HaMikdash. Plato met Yirmiyahu at the Temple Mount weeping bitterly over the ruins of the Bais HaMikdash. Plato asked him two questions.
1) How is it befitting for such a preeminent sage in Israel and such intellectual stature, to cry over a building which is really no more than a pile of sticks and stones?
2) The building is already in ruins, what good will your tears do now? Why cry over the past?
Yirmiyahu responded by asking Plato if as a renowned philosopher, he had any perplexing questions. Plato recited a long list of complicated questions, whereupon Yirmiyahu, humbly and quietly, solved them in a few brief sentences. Plato was dumbfounded. He could not believe that any mortal man could be so wise. “All of this profound wisdom I derived from those ‘sticks and stones’ and that is why I’m crying. As for why I’m crying over the past, this I can’t tell you because you will not be able to understand the answer.”
The Mishna (see Avos 6:6) states איזהו חכם, המכיר את מקומו, who is the wise person? One who recognizes his place. When Adam sinned, HaShem presented Adam with a one word question, אַיֶּכָּה, where are you? The Medrash (Bamidbar Rabbah 19:9) states that just like HaShem brought Adam into Gan Eden and then banished him and lamented over Adam with the word אַיֶּכָּה, He also brought the Jewish People into Eretz Yisroel and banished them, subsequently lamenting their exile with the word אֵיכָה , how (could she dwell alone)?
The Jewish People were exiled because they forfeited their wisdom, as it is said (Yeshaya 5:13) לָכֵן גָּלָה עַמִּי מִבְּלִי דָעַת, therefore, my people is being exiled because of ignorance. The Bais HaMikdash represented the seat of wisdom in this world, and the destruction and exile symbolized the loss of wisdom for the Jewish People. It is no coincidence that following the month of Av, the month of destruction, we enter into the month of Elul, a time of renewal and introspection. The word חכם, wise person, is the same gematria as the words אלול, לולב and חיים, life. Teshuva, repentance, comes from דעת, knowledge. It is for this reason that we ask HaShem for knowledge in the fourth blessing of Shemone Esrei, and we immediately follow this supplication with the request that we be allowed to repent. Only one who has knowledge and wisdom can repent properly. Once one has fully repented can he be restored to his original place of wisdom. Sukkos and its accompanying mitzvos represent the Bais HaMikdash, the seat of wisdom. HaShem should allow us to use the forty days of Elul through Yom Kippur for true repentance and wisdom, and forty represents knowledge and repentance, as it is said (Yeshaya 6:10) וּלְבָבוֹ יָבִין וָשָׁב וְרָפָא לוֹ, and understand with its heart, so that it will repent and be healed, and the Baal HaTurim (Devarim 8:4) writes that the word לְבָבוֹ equals in gematria 40.