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How does one 'make themselves poor' on Rosh Hashanah, as the Gemara (גמרא) 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 (ה׳) as truly poor people - asking for everything anew based solely on His chesed (חסד) - paradoxically creates the zechus and devekus that leads to true spiritual wealth.
This shiur presents a profound approach to Rosh Hashanah based on a letter written by Rav Shlomo Wolbe while he was hospitalized in America. The letter draws from a Gemara (גמרא) in Rosh Hashanah 7b which states that 'any year that is poor at its beginning will be rich at its end.' Rashi (רש"י) explains this refers to the Jewish people making themselves 'poor' on Rosh Hashanah by speaking with beseeching and prayer, like a poor person who has nothing and begs for everything. Rav Wolbe asks a fundamental question: how does one 'make themselves poor' and what does this mean practically? He explains that Rosh Hashanah is not merely an annual judgment, but represents 'yom t'chilas ma'aseicha' - the beginning of creation itself. It's both a tremendous opportunity for a fresh start and a sobering reality that nothing we currently have can be taken for granted. Whatever parnassah, health, family, or any blessing a person has accumulated cannot be assumed to continue. On Rosh Hashanah, there is a new din (judgment) for everything.
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Rosh Hashanah 7b
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