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What does it mean to "cast your bread upon the waters" (Koheles 11:1)? True chesed (חסד) means investing in people without maintaining control or expecting gratitude, rather than giving with strings attached. When we help others as investors rather than creditors, we empower their growth and earn a genuine share in their success.
Rabbi Zweig begins this pre-Rosh Hashanah shiur by sharing wisdom from the Alter of Slobodka, who taught his students that the primary preparation for Rosh Hashanah should be helping younger students in the yeshiva - emphasizing chesed (חסד) as the main avoda for the Day of Judgment. This sets the stage for analyzing Koheles 11:1: "Cast your bread upon the waters, for after many days you will find it." Rashi (רש"י) explains this verse through the example of Yisro, who showed kindness to Moshe at the well without knowing he would ever see him again, yet ultimately became his father-in-law with descendants who sat on the high court. However, Rabbi Zweig notes that Rashi strangely focuses on what Moshe accomplished rather than what Yisro received, suggesting a deeper meaning than simple reciprocal reward.
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Koheles 11:1
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