Two Approaches To Koheles

Rav Eizak Sher, Rosh Yeshiva of Chevron (Leket Sichos Mussar) brings two distinct approaches from two of the great mussar giants, Rav Itzeleh Peterberger and the Alter of Slabadka as to why on Sukkos, a holiday of great joy, the sad and depressing book of Koheles is read.  Rav Itzeleh said that we are strengthening our commitments from Yom Kippur that indeed this world is empty and meaningless and it’s ruchnious that counts.  The Alter said there is an element of great joy in the Megillah for we learn that from hevel havalim one can make holiness.  (Each one’s answer followed their approach to mussar as Rav Itzeleh was from the old school of the mussar movement which put more of a focus on the negative of man but the Alter was from the new school that focused on the greatness of man.)

Rav Dovid Solevetchik says along the lines of the first approach but he also throws in a picture of the simchas beis hashoevah in Volozhin.