Megilat Kohelet is one of the most difficult books in Tanach: it jumps back and forth between conflicting assumptions, it lacks any obvious narrative or thematic structure, and its statements sometimes seem at odds with what most people would consider standard Rabbinic theology. People didn’t discover these problems today, of course; the Mishnah in Masechet Yadayim questions whether Kohelet was canonized as part of the Bible or not. Moreover, Masechet Shabbat 30b reports in the name of Rav that the Sages wanted to hide Kohelet because of its contradictions; they decided against it because its beginning and end are words of Torah - and as Rashi explains, that means that surely there must be other words of Torah in the middle. Still, the fact that they even considered this tells us that Kohelet was as mysterious to them as it is to us. We read Kohelet on Shabbat chol hamoed of Sukkot - or, in a year like this where there is no Shabbat during chol hamoed, on the first day of Sukkot in Israel, or on Shmini Atzeret outside of Israel. But going through all twelve chapters quickly in shul is not the best way to internalize the many messages of this intriguing book. For that reason, Scott was extremely gratified to welcome Dr. Erica Brown back to the podcast. Erica is the author of Kohelet and the Search for Meaning, and they discussed some of the many questions that are raised by Kohelet. It’s a wide ranging and fascinating conversation that invokes Shlomo HaMelech, the Byrds, C.S. Lewis, William Blake, George Carlin, Sesame Street, and more. It will give you a new appreciation for Kohelet not only as a sacred text, but as a book that speaks directly to the deepest concerns of human beings living in the 21st century. Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108). Check out the Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse. Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com