The Gemara says that during the Aseres Yimai Teshuvah (Ten Days of Repentance) the gates of prayer are open, and that’s the time to ask for our heart’s desire. Whether we want to succeed in learning Shas (Talmud study) or we want to succeed in business, or we want both, Aseres Yimai Teshuvah is the time. Of course the more we ask, the more we’re going to succeed.
It’s important to understand how our forefathers considered this subject of praying. When Yaakov Avinu was talking to his children about the land of Canaan, he said,
“Asher lakachti m’yad haEmori b’charvi u’b’kashti — The land that I took from the hand of the Emori with my sword and with my bow” (Beraishis 48:22).
It sounds like Yaakov had been carrying on a military campaign, only the Chumash doesn’t speak about it. It could have been that Yaakov didn’t have to take anything by battle, but like one of our former presidents said, “Speak softly and carry a big stick.” So Yaakov took the land by his sword and bow. He didn’t use them, but wherever he went he was well armed. When he needed something, he took it by negotiation, he paid for it, but no one attempted to wrong him because they respected his military preparations.
This could have been the case, but the Gemara says that the word u’b’kashti should be read bakashasi, which means “my request,” “my prayers.” Yaakov Avinu took the land “b’tzilusi u’meusi — by my prayers.” “Charbi zu tefilah, kashti zu bakashasi — ‘My sword’ is prayer, ‘my bow’ is my entreaties.” When we stand before Hashem on Rosh Hashanah, we’re well armed with a lot of intention, and we pray from the bottom of our hearts, that’s how we’re going to win out against all the vicissitudes that may face us in the ensuing year.
Making entreaties means we are persistent. We ask for something, are not hesitant, and repeat our requests. We shouldn’t begrudge the hours that we spent in the synagogue on Rosh Hashanah because those hours, if spent properly, will have effects that we’re going to witness during the entire ensuing year.
Source: Rabbi Avigdor Miller zt”l