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 27:26, the Torah states אָר֗וּר אֲשֶׁ֧ר לֹֽא־יָקִ֛ים אֶת־דִּבְרֵ֥י הַתּוֹרָֽה־הַזֹּ֖את - cursed is the one who does not uphold the words of the Torah. R' Frand asked why does the Torah use the word uphold (Yakim) and not keep (YiKayem)?
R' Frand answered by quoting the Ramban who explains that this refers to someone who says - I will keep the whole Torah, but not this particular mitzva that I don't understand or that I don't agree with. This person is not failing to keep a mitzva because he has a desire or because he his lazy. That would not be a reason that a person should be cursed as he is merely being human. But a person who says that he fundamentally will not follow a particular rule, that is a person who is cursed.
R' Frand next quoted the Chazon Ish who explained that in Klal Yisrael there are Tzaddikim and there are also good men, even if they are not on the level of being a Tzaddik. This second category of people strive to be Tzaddikim, but are held back because of their Yetzer Hara. But there is also a third category of people who are happy with not being perfect and have no desire to grow. As we approach Rosh Hashanah we should want to be in that second category of desiring a year so that we can grow.
R' Frand said a second vort which contrasted the Berachos and Klallos which both the use word וְהִשִּׂיגֻ֑ךָ - and they will come upon you and overtake you. In Devarim 28:2, the Torah writes וּבָ֧אוּ עָלֶ֛יךָ כָּל־הַבְּרָכ֥וֹת הָאֵ֖לֶּה וְהִשִּׂיגֻ֑ךָ - the Berachos will come upon you and overtake you. But in Devarim 28:15, the Torah writes וּבָ֧אוּ עָלֶ֛יךָ כָּל־הַקְּלָל֥וֹת הָאֵ֖לֶּה וְהִשִּׂיגֽוּךָ - the Klallos will do this.
It is understandable why a person would want to avoid the Klallos and thus they will overtake him, but why would someone want to avoid the Berachos?
R' Frand gave a number of answers, some of which I will summarize here. R' Frand quoted R' Shimshon Refael Hirsch who explains that the person whose Berachos will overcome him is a person who does mitzvos because he wants to do mitzvos and not for the sake of a reward. This person will be overcome with Beracha, even though he is not expecting it.
R' Frand also quoted R' Weinberger in Shemen HaTov who writes that it will occur that a person will become wealthy and it will change the person, or a person will be overcome with troubles and it will change his countenance as well. The blessing here is that the person will be overcome with Berachos which will not change him, while the Klallos are that he will be overcome with troubles which will change him too.
Lastly, R' Frand quoted the Degel Machaneh Ephraim which explains that there are times that Hashem will send us a beracha which we do not capitalize on. Maybe because we don't understand that its a blessing or perhaps because our nature is not to jump at potential opportunities which involve change. Hashem says - I will send this beracha and it will overcome you, even if you are trying to avoid it.
R' Frand closed the vort by quoting the pasuk in Tehillim אַ֚ךְ ט֣וֹב וָחֶ֣סֶד יִ֖רְדְּפוּנִי . Why would we need goodness and kindness to pursue us? Because there are times that we don't see that something is a Beracha and therefore we need it to pursue us.
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