Famed late Mashgiach of Yeshivas Bais Moshe Chaim, His shiurim are a staple of the Yeshiva.
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How does one 'make themselves poor' on Rosh Hashanah, as the Gemara in Rosh Hashanah 7b requires? A letter from Rav Wolbe explains that since Rosh Hashanah represents a complete renewal of creation, we must recognize that nothing we have belongs to us by right. Approaching Hashem as truly poor people - asking for everything anew based solely on His chesed - paradoxically creates the zechus and devekus that leads to true spiritual wealth.
Why does Rosh Hashanah come before Yom Kippur when it seems logical to receive forgiveness before judgment? The shiur explains that Rosh Hashanah's acceptance of divine sovereignty creates a new identity that gives us standing to request kapara on Yom Kippur. We're no longer asking God to ignore our sins but to treat past actions as truly past since we've become different people.
Why doesn't the Torah explicitly mention Olam Haba if it's our ultimate goal? The Maharal's answer: Torah's purpose is to perfect this world, not the already-perfect World to Come. This means our mitzvos must create real meaning and connection now, not just earn future reward like meaningless busywork.
