This was the sin of R Akiva’s students. “The Torah’s ways are pleasant.” (Mishlei 3, 17) If there was a slight lack of interpersonal propriety on the students’ part, then that means that they were failing to fulfill the Torah. They may have been outstanding scholars, but what good was their erudition if they lacked the fundamental ability to connect what they learned to their lives?
Perhaps this is why Hashem wants us to count every day from Pesach to Shavuot. If the Torah was merely one of the sciences, then it would be sufficient to include it in our lives on a semi-regular basis, but Torah is more than a science. The Toras Chaim is a Divine Instruction Manual for every day of our lives. Hashem wants us to grow in our ability to serve Him daily so He instructed us to practice incorporating Divine Service into our daily routines. There are no days off; if you skip a day, you’re missing the point. A Jew serves Hashem every day of his life without exception.
This is the lesson of the vav. Vav is a letter that connotes connection. The vav hachibbur means ‘and’ because it connects two distinct phrases. Additionally, the word vav means ‘hook’. A hook connects two disparate objects. The avodah of Iyar lies in learning how to approach every day trying to apply what we know about Hashem’s will to our lives. A Jew must learn to understand that he not only must learn the Torah (which is perhaps what we will do in Sivan after matan Torah), but also must connect the Torah to our daily lives. Judaism is not just for the shul, it’s for every aspect of every day.
Let’s sum it up by explaining why Yissachar is aligned with Iyar. You see, Yissachar is not the only Torah tribe, we also have Levi, whose primary job is to study and teach the Torah, but Yissachar has a unique responsibility. As the Rashi we quoted earlier taught, Yissachar was the one who provided practical halachic decisions for the Jewish people. Yissachar was the one who enabled Klal Yisrael to connect the Torah to everyday life. They turned the Torah into a Toras Chaim. The reason Yissachar is placed in the month before matan Torah is because his middah (of understanding and feeling that Torah is not just to study, but also to fulfill) is a prerequisite to being worthy of receiving the Torah. As we quoted earlier from the Sifri, when Hashem heard that the nations were not willing to fulfill the Torah, He backed off and found a different nation to whom He could give it. May we merit growing in our ability to feel that every day of our lives must be based on Torah, and in that way may we become worthy of receiving it next month and making Hashem proud.