The following is a brief summary of some of thoughts said over by R' Frand on Rosh Hashanah 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.
R' Frand began the vort by noting that the Gemara in Rosh Hashanah (33b) states that we learn aspects of Rosh Hashanah from the mother of Sisra. The holiday is called "Yom Teruah" but we don't know what that it is. The Targum calls Teruah - Yevava and the Gemara says we learn Yevava from the mother of Sisra. The pasuk in describing the mother says VaT'Yabev from which we learn that she was crying.
R' Frand quoted the Tosafos in Rosh Hashanah which writes that there is a minhag to blow 100 blasts, although from the Torah one only needs to hear 9 blasts and someone who comes late can fulfil their obligation with hearing 30. But because she cried 100 times, we learn the 100 blasts from her.
But why is she the source of the rule? There are many mothers who were answered on Rosh Hashanah, including Sarah and Chana!
R' Frand answered that this was due to Sisra and his history in battle. He always won (before doing battle with the Jews) and his mother always expected to see his chariot carrying him home...until this time. His mother cried out when what she expected did not happen and R' Frand said that this is the lesson to us - that we should not expect to come out on top simply because we had been judged favorably in the past. R' Frand used the loshon - there is no Chazakah in judgment. Merely because a person has health or wealth, it is not a guaranty, as you never know.
R' Frand quoted the selichos which we say every morning. We say that we are knocking on Hashem's doors like poor people. R' Frand quoted R' Pam who said that we don't know what will be in judgment.
R' Frand also quoted the Satmar Rav who observed that the holiday is "Ba'Keseh" - its the only holiday where the moon is hidden. This natural phenomenon reflects the essence of the day - we don't know.
R' Frand said that every year people ask him after Rosh Hashanah how his holiday was. He always answers - ask me again next Erev Rosh Hashanah, because you just don't know. And if there is one lesson that we can say we learned from 5781 - it's that you just don't know. Look what the world has gone through - there is no one who does not know someone who died in the past year.
[On a personal note, we lost our great Rav - Rabbi Kelemer Z'TL. I would have loved for my son-in-law, aka the Young Rabbinical Scholar, to have met him and talked in learning].
R' Frand then quoted a commercial he had seen in the Wall Street Journal for a cruise which National Geographic is sending people to Antarctica. He said that there is a tag line - The Pandemic Taught us that Our Bucket List has to be Our To Do List. That may be the Wall Street Journal - but the pandemic taught us that we can't take anything for granted.
R' Frand quoted R' Dovid who quoted R' Yisrael Salanter who said that there is a segulah to come out ahead in judgment - it is do for others and to live for others. He said that people in the US, people live for themselves. They "choose" not to have children. He remarked that he reads the obituaries and sees that people have "1 grandchild." This is not living for others.
R' Frand said that there was an article in Mishpacha Magazine which discussed a lack of leadership. R' Frand opined that living for others does not mean that you have to start your own organization. Every town has a chessed organization that needs help and getting involved in an organization like this makes a person more vital.
R' Frand said a vort which I heard previously from R' Mansour about the insert in the davening of Yamin Noraim Shemoneh Esreh - Zochreinu L'Chaim. We ask for life L'Ma'ancha - for Your sake Hashem. R' Frand explained that we are saying - Hashem we are living for You, to be selfless and do for others. And the more that a person does for others, makes him worthy of being matzliach in the judgment. This does not require a person to be the Gadol HaDor - even in one's own family. This makes a person more vital and he can say to Hashem - I am asking for life so that I can do for You.
R' Frand said that IYH we should see the real end of the pandemic and the end of the acts of anti-Semitism and Hashem should bench us to end all of our troubles. Amen.
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