While I can never do justice to any speech I hear, I’m going to try to give a brief summary of what Rabbi Gottlieb said last night before selichos.
He said that as we approach Rosh Hashanah, we’re left with conflicting feelings. On the one hand, we’re looking forward to a new year, a fresh start. On the other hand, what has changed since last year? We all have things that we said we’d work on last year, yet find ourselves in the same predicament; are we going to change this year? While we are supposed to enter Rosh Hashanah with confidence that we will have a good outcome (which is why we shave, get haircuts, and wear nice clothing), it is this insecurity with our actions and their possible effect on our outcome that fuels our kavannah (concentration) in our davening.
Insecurity has had very signifanct results in history. Rabbi Gottlieb mentioned that the reason we blow 100 shofar blasts on Rosh Hashanah is because we are counteracting the one hundred cries of the mother of Sisra. It seems odd that we’d have shofar blasts in correspondence with such an evil person. But the reason is because of the mother’s uncertainty and insecurity. When Sisra went to battle and his mother didn’t hear back from him, she was uncertain if he had had the greatest victory of all time and was celebrating, or, and more depressing for her to think about, perhaps he had suffered a great defeat and even killed in battle. With this insecurity in mind, she let our her 100 cries. (There’s more on that here.)
It was very apropos that 9/11 occurred approximately one week before Rosh Hashanah. This happened about a year after the Intifada in Israel had started, and since it was Elul, many parents chose not to send their children to Israel for the year because they were afraid of all the bombings. In other words, they were insecure with sending their children there. Yet just a few weeks into Elul, the planes smashed into the Twin Towers showing everyone that no one is secure anywhere, and the only way to actually be secure is to place your trust in God. With the towers collapsing, people realized just how insecure they were anywhere.
This insecurity is what drives us and we should take the insecurity to motivate us to daven properly and with full kavanah so that we can merit to be properly secure in our relationship with Hashem to do His will.