With the nearing of any of the major points on the Jewish calendar, we begin to learn and analyze the customs and practices associated with that event. As Sukkot is approaching, it is only appropriate that we take a deep look at the Mitzvot, Minhagim, and Tefillot of the Chag, not just taking note of what they are, but also why we do them. We look to see how our actions on Sukkot parallel the deeper meaning, message, and theme of the Chag.
With that in mind, a quick glance at the reason why Ashkenazic Jews read Kohelet on Shabbat Chol HaMoed has the potential to leave any curious learner puzzled. The Magen Avraham (490:8) writes that “[on Sukkot] we read Kohelet because they are days of joy and it states in Kohelet (2:2) ‘what does it [joy] accomplish?’” The Magen Avraham tells us that on Sukkot, such a happy Chag, we must read Kohelet, for it addresses, analyzes, and even bashes that very same state which is the theme of the day. How does Shlomo HaMelech’s philosophical work, which at its core challenges the benefits of joy, line up with the overall theme of happiness on Sukkot? Why do we publicize this seemingly negative view of Simchah on Yom Simchateinu, a day of happiness? It appears that the message of Kohelet contradicts the very message of Sukkot!
The Peri Megadim suggests that perhaps, the answer to this difficulty lies in the specific type of happiness about which Shlomo HaMelech warns future generations. Happiness which stems from places of impurity lies dangerously close in nature to frivolity and is therefore something to be avoided. Ultimate, true, and pure happiness comes from devotion to the Mitzvot and the fulfillment of the Ratzon Hashem. This is the Simchah for which Sukkot is named; this form of Simchah is the theme of the Chag. The Peri Megadim explains that there is no contradiction in the reading of Kohelet on Sukkot, since it is necessary at a time when we are so focused on Simchah to remind ourselves of exactly what kind of joy we should experience and strive to achieve. We must realize that we rejoice before Hashem for seven days not with frivolous Simchah consisting of just eating and drinking, but rather with the pure joy of observing the Mitzvot. We must push ourselves to keep in mind, even at a time in which we focus on our own personal satisfaction that we are devoted to a higher cause, and that is why we are happy in the first place.