Once on a שבת מברכים I asked מורי ורבי הרה"ג ר' שלמה מילר שליט"א at the start of Davening, we ask Hashem,
—that we should not be brought to a נסיון. Yet, during ברכת החודש, we ask for עשירות which often brings with it greater נסיונות than those faced by someone who is not wealthy.
He answered,
We begin ברכת החודש with the words,
The words לטובה ולברכה apply to all the בקשות that follow.
Therefore, when we ask for עשירות, we are not simply asking for wealth. We are asking for עשירות לטובה ולברכה—that the wealth should be a genuine טובה and ברכה, and should not bring with it נסיונות that we cannot handle. We are asking that, together with the עשירות, we also have the ברכה of being שמח בחלקו and of using the wealth properly.
* Years later, I found the Chasam Sofer on the pasuk, “עשר תעשר – בשביל שתתעשר,” citing the Midrash, which adds, “ובשביל שלא תתחסר.” The Chasam Sofer explains this Midrash with the pasuk in Mishlei,
—the blessing of Hashem brings wealth, without any accompanying sadness or harm.
This was precisely R’ Shlomo Miller's insight that he had conveyed to me: עשירות that comes together with ברכת ה׳ is the עשירות we are asking for at ברכת החודש; it does not bring with it the “עצב” or harm.
* Today I came across the ספר פניני שלמה מאת ידידי הרה"ג ר' עזריאל יהודה גשטטנר שליט"א where he quotes Reb Shlomo Miller's חידוש on עשר תעשר & the Chasam Sofer ושמח לבי
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