Lehallel
Getting it ready…

Torah · 6:27

When Is Chutzpah A Good Thing?

256 views · May 12, 2026

Rabbi Dovid Orlofsky

Ask this shiur

Ask in your own words — the answer is the exact moment this shiur speaks to it.

What’s said in this shiur

The opening of this shiur, in Rabbi Dovid Orlofsky’s own words — taken from the captions, so names and Hebrew terms may be approximate.

Hi, this is Rabbi Wolasky with our question and answer series where in a few minutes we try to give you an answer to a question that might be itching you. I'm itching to get an answer. My brother at his 25th wedding anniversary quoted uh from Eishes Chayil and said, you know, how Eishes Chayil, the good wife, more precious than pearls. He says, how do you get a pearl? He says, a little piece of sand gets into a oyster and it irritates it and it releases the lucra to cover it up because it's irritating them. So, sometimes the things that irritate you help to create great pearls. Right? K'neinim in in Eishes Chayil. So, when I got up to speak, I said, I didn't follow his whole speech, but basically his wife irritated him until he agreed to buy her pearls. So, uh that's not exactly how it works, but anyway, when is chutzpah a good thing? That's real rough. Ki ein anachnu azai ponim k'shei oref lomar l'fanecha Hashem Elokeinu v'Elokei avoseinu tzadikim anachnu v'lo chatanu avosainu anachnu avosainu chatanu. We are not so brazen. One of the things we clap al cheit for is an azus ponim. Chutzpah. Yeah. And uh chutzpah is uh is is a terrible thing. Yeah. Pikei Avos says, azus ponim l'gehenim. And uh it's a it's a very rough thing, chutzpah. So, where, if ever, is there a role for chutzpah? So, um there was this fellow who wanted to get into Reb Moshe Shapiro's Tuesday shiur, but it was really only for married people and he was single. But, he couldn't go to the Thursday shiur which was open to the general public. He wanted to get to one of the mayor's sheer. And he says, "What can I do? It's only for married people." He says, "But I have a special skula to become a ben Torah."

Jump to a moment

  1. 0:00Hi, this is Rabbi Wolasky with our question and answer series where in a few minutes…
  2. 0:32the lucra to cover it up because it's irritating them. So, sometimes the things that irritate…
  3. 1:04lomar l'fanecha Hashem Elokeinu v'Elokei avoseinu tzadikim anachnu v'lo chatanu avosainu anachnu avosainu chatanu. We are…
  4. 1:36chutzpah. So, where, if ever, is there a role for chutzpah? So, um there was this…
  5. 2:39So, every Jew is at a disadvantage because since he's a byshan and ain't byshan lo…
  6. 3:12I mean, obviously, you have to ask your respect, >> [clears throat] >> but you have…
  7. 3:43name you want. You can do whatever you want to me, but you're the only one…
  8. 4:47don't argue with someone who can turn you into a frog, you know what I mean?…
  9. 5:19is a chutzpah. We came here and we built the country and and we kicked out…
  10. 5:50all right if I sit over here? Is this a problem? Can I come in?" And…

Every second of this shiur plays inside Lehallel — a filtered YouTube library of Torah, music and shiurim. No ads, no comments, no autoplay.

More from Rabbi Dovid Orlofsky

Get the week’s best, by email

One email a week — a handful of shiurim and music. No account needed.

Know a family who would use this? Give a Lehallel membership.