The following is a brief summary of some of thoughts said over by R' Frand on the parsha this evening. I have attempted to reproduce these vorts to the best of my ability. Any perceived inconsistency is the result of my efforts to transcribe the shiur and should not be attributed to R' Frand.
In Devarim 29:18, the Torah states וְהָיָ֡ה בְּשָׁמְעוֹ֩ אֶת־דִּבְרֵ֨י הָֽאָלָ֜ה הַזֹּ֗את וְהִתְבָּרֵ֨ךְ בִּלְבָב֤וֹ לֵאמֹר֙ שָׁל֣וֹם יִֽהְיֶה־לִּ֔י כִּ֛י בִּשְׁרִר֥וּת לִבִּ֖י אֵלֵ֑ךְ לְמַ֛עַן סְפ֥וֹת הָֽרָוָ֖ה אֶת־הַצְּמֵאָֽה.
R' Frand focused on the end of the pasuk where the brazen person who says that he will do as we wishes has "thereby adding the watered upon the thirsty." R' Frand remarked that the language is difficult to understand (even with that Artscroll translation).
R' Frand quoted Rashi's explanation that the person had previously sinned out of desire - like one who is thirsty. Now, the person sins because he thinks that he can do whatever he wants, and not because of simply being overcome. The person who does so will have his unintentional sins punished in the same way as his intentional acts.
R' Frand then quoted the Gemara in Sanhedrin 66 which states that a person who returns the lost object of an Akum is the subject of the end of this pasuk - that there is no mitzvah to return the object and the person will not be forgiven by Hashem (the beginning of Devarim 29:19). If a person returns the object because he wants to be seen as having a good heart (בִּשְׁרִר֥וּת לִבִּ֖י אֵלֵ֑ךְ), it is a sign that he does mitzvos not because he was commanded to, but because it feels good in his heart.
Rashi on the Gemara ties this back into the language of the pasuk, remarking that the one who is not thirsty is the Akum who does not desire mitzvos. The person who is thirsty and wants to be closer to Hashem should do mitzvos out of a desire to draw closer to Hashem.
R' Frand tied this thought into the Rambam on Shofar who explains that the purpose of the Shofar on Rosh Hashanah is to awaken a person who is involved in worldly pleasures (havalim) to do teshuva. For this reason a person does teshuva during the ten days of repentance by doing mitzvos - between man and Hashem and between man and man and does additional learning and gives charity.
R' Frand asked - what is the connection between the havalim and the Shofar and since when does one do teshuva on Rosh Hashanah? There are no Al Cheit which are struck. So why does the Rambam call this a day of teshuva?
R' Frand answered by quoting R' Moshe Shapiro who says that a person does do teshuva on Rosh Hashanah and it is different than the remainder of the ten days. The other days are the days of teshuva for what a person did over the past year. But on Rosh Hashanah we do teshuva by removing the worldly pleasures and think about what we can do to live a life without the physical pleasures - it is this that the Shofar inspires us to do.
R' Frand closed the vort by noting that all year people may eat bread of an Akum baker (of course under supervision) but during the ten days of teshuva a "Ba'al Nefesh" should be stringent. But what is a Ba'al Nefesh?
R' Frand quoted the Tolner Rebbi, who explains that term means a person who thinks about his nefesh. All year long a person thinks about the body - am I exercising enough? Do I make enough money? But during these days he should think about his nefesh and this is the purpose of the Shofar - to awaken him.
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