About this shiur
Rabbi YY Jacobson discusses his journey with Rabbi Russell at Kesher Nafshi 2026.
A 1h 20m hashkafa shiur by Rabbi YY Jacobson. Like every video on Lehallel, it was judged and approved under the Lehallel law before it ever appeared — no unreviewed result is ever shown.
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Rabbi YY Jacobson has 2,708 approved videos on Lehallel across Chassidus, Daf Yomi, Halacha — every one reviewed against the same written standard before it appears.
Recently approved from the same speaker: “Chassidus Friday - Aug 7: Likkutei Torah Reah Anochi #3” (1:47:42) · “Rabbi YY Jacobson: Chassidus Monday - Aug 3” (1:44:34) · “Don’t Substitute Authentic Connection for Anything - Women's Tu B'av Class 5786” (1:29:53).
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What’s said in this shiur
The opening of this shiur, in Rabbi YY Jacobson’s own words— taken from the captions, so names and Hebrew terms may be approximate.
>> And as he did to me on numerous occasions, he has not seen the questions I'm about to ask him. But we're going to dig deep tonight. >> [snorts] >> We're going to dig deep tonight. So I want to return the favor. I remember sitting on a very cold winter's day in the basement by Rabbi Jacobson's house when we did a a conversation. I thought it was a a conversation. I thought it was a conversation. Turned into a grilling. And Rabbi Jacobson asked me a very interesting question out of the gate. He warned me that uh his wife had recommended he should not ask this question. But uh in his infinite wisdom, he decided guided by the Ein Sof that he would ask me the question. The question was gevaldig. I actually question was gevaldig. I actually appreciated the question because in Keshen Afshi we get real. So the question he had asked me then which I think surprised everyone was uh with a big smile on his face, he said to me "Rabbi Russell," he said, "uh you're considered an important person in the world of Chinuch. Today, people respect you and they you know, they you they follow your advice. So, perhaps you can comment on how it was that you had six kids off the was that you had six kids off the derech. This was his opening question. Live [clears throat] to the world. It went viral. There was 100,000 hits in 3 months of this drasha. So, we get real in Keshen she's someone who turned the favor, my dear friend. >> [laughter] >> I want to know if what your wife had to say about that question. >> tell her. I didn't tell her. I didn't even ask her
Jump to a moment
- 0:32>> And as he did to me on numerous occasions, he has not seen the questions…
- 6:11What should have uh been a very successful life, and it appeared to many I assume…
- 12:23families. If you informed on your mother or your brother or your sister, you were elevated…
- 18:31listening to speeches that are just simply inauthentic. And it's not that the speakers are the…
- 24:48most important consequences was I can't say constantly, that wouldn't be true. But there are moments…
- 30:58supposed to show off your merchandise, right? >> [laughter] >> Everybody comes, they're in a good…
- 37:09have taken upon themselves with mesirus nefesh the task of cracking open their parents. Because you…
- 43:16>> you know I just just to you reminded me of a story that happened to…
- 49:26And this is how so many of us have been trained. A lot of our parents…
- 55:31And it's driving us crazy. So we try to bring them to professionals, whatever that means,…
About Rabbi YY Jacobson on Lehallel
2,955 approved videos from 2010 to 2026, 2,806 of them searchable by their own words. Open all of Rabbi YY Jacobson’s shiurim →
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Key takeaways
- Hashkafa — 1h 20m, by Rabbi YY Jacobson
- Approved by the Lehallel judge before appearing — never an unreviewed result
- Watch free during prelaunch on Lehallel
Watch this now
Don’t just read about it — watch it
My Journey from the Mind to the Heart1:19:39
Chassidus Friday - Aug 7: Likkutei Torah Reah Anochi #31:47:42
Rabbi YY Jacobson: Chassidus Monday - Aug 31:44:34Every video is reviewed against one written standard before it can play.