On the night of his birthday, Zacharia asks Reuven what he'd tell his 20-year-old self. Turning the question around Reuven says he's hearing what  that 18-year-old, hitchhiking across Canada and drawing through the night at a Vancouver diner, been telling him?

The conversation moves from there. Dr. Edith Eger's line about being pushed by pain or pulled by dreams. Why people who feel stuck often can't name what they used to love. Dr. Twerski calling a twelve-step meeting the most spiritual moment of his life. What it means to confess to someone you feel safe with, and whether that's the model for Yom Kippur. A young man at Aleinu who kept offering a hand up that wasn't needed. And a striking Rashi on "Avi v'imi azavuni, v'Hashem ya'asfeini", My father and mother abandoned me, and G-d gathers me."

Reuven shares his hachlatah -  decision for the year he enters his seventh decade: to review each night which middos he expressed that day, and what thinking drove them!

Are  Rosh Hashanah and Yom Kippur and the days in between about becoming worthy? Isn't this what "better through regret" means?

In this post-Rosh Hashanah farbrengen, Reuven and Zacharia wrestle with a radical idea: creation itself doesn't have a reason. Blowing the shofar, which changes everything, makes no sense — it is a gezeiras hakasuv, a decree. Don't explain it, understand it, or find meaning in it — simply accept the no rhyme or reason. Why? This begins our relationship with Hashem. As such if there's no reason for creation, value and worth have no place.

From the first day of Rosh Hashanah on Shabbos, when the shofar isn't blown, to the second day when we do blow it, the conversation explores emunah - faith and belief, oneg - pleasure, anxiety, Chassidus, and the difference between improving yourself and trying to prove yourself.

What would happen if we stopped using Torah, achievement — even spirituality — to establish our value?

Learning Chassidus to become "more frum" ( religious) is actually a subtle scam you're running on yourself. Creation has no reason. G-d doesn't fit the logic. So why are you still trying to "earn by learn" - to claim your value? 

This is "87" -   Paz — the year of pure gold — and what it actually means to stop negotiating for your own worth. A year of "pure gold" — not because of what we accomplish, but because our worth was never ours to manufacture, but to accept.

Rosh Hashanah isn't just the head of the year—it's meant to lead the year. Reuven and Zaharia wrestle with what it means to make a real hachlata: not simply another goal, another page of Gemara, or more words of Tehillim, but a commitment that actually changes the person making it.  

What if davening isn't asking Hashem to change our circumstances, but asking for the power  to change ourselves and our circumstances? And what if the hard work we're avoiding is actually where oneg—our deepest pleasure—is found? 

A Street Farbrengen about Rosh Hashanah, commitment, oneg, personal responsibility, crowning Hashem as King, and the uncomfortable difference between living by habit and choosing who you're going to become.

Be Born.

We talk a lot about bittul—surrendering ourselves to something greater. But somewhere along the way, did we begin confusing bittul with weakness?

Chai Elul celebrates the birthdays of the Baal Shem Tov and the Alter Rebbe. But why birthdays? What does birth itself tell us about the the  essence of what is Chassidus?

Maybe the answer is startlingly simple: Before you're born, your life comes through someone else. After birth, the life is yours.

In this episode of Street Farbrengen, we wrestle with spiritual independence, personal ratzon, the difference between humility and helplessness, and an uncomfortable question: Why is it sometimes easier to say “Hashem wants me to become this” than simply to say “I want to become this”?

From Chai Elul to Rosh Hashanah, from bittul to personal power, we explore a paradox at the heart of Chassidus:

The power isn't yours. But it was given to you as yours.

The Rebbe wasn't interested in creating followers. He wanted leaders.

Maybe it's time to be born.

Is G-d Waiting to Punish You? |

We each carry pictures of G-d in our heads or a sense of "personality."
Is your picture of  G-d keeping score, waiting for you to slip up? Do you need more zechusim, merit and worth, more segulos magic potions, more blessings  to make it safely through another year?

Have  we taken the language of schar v’onesh—reward and punishment—to make G-d into the 'principal standing over us with a yardstick?

In this episode of Street Farbrengen, Reuven and Zacharia dig into the emotional picture of G-d that our contemporary society and experience creates within us.

They explore fear as a religious motivator, consequences versus punishment, our need to control and explain what happens to us, the Chassidic meaning of l’maalah min haseichel, above your mind , and the strange power of the shofar—a ram’s horn upon which, somehow, an entire year turns on.

And underneath it all is one uncomfortable question:

What have I made G-d into?

Throughout Elul  and as Rosh Hashanah approaches, maybe the work isn’t simply becoming more afraid.  Maybe it’s learning to go see G-d.

A farbrengen is not a class. Nor a therapy session. Not a place to walk away with a tidy answer or a checklist of things to fix. 

In this conversation, we dig into what separates a farbrengen from a glorified pep talk — and land on something simpler and harder: vulnerability, brought honestly to the table, with no guaranteed resolution at the end.

Along the way: a Rashi on Psalm 27 and what it reveals about G-d's presence in the most unlikely moments of life; the idea of writing a personal manifesto — and what it costs an entrepreneur, or anyone, to actually name what they're willing to fight for; a story about a yeshiva student saved by nothing more than someone else admitting "I have the same problem"; and a long look at the Rebbe's image of the King in the Field — what it means to find G-d not in the palace, but in the mess, the ordinary, the human.

We also talk about therapy culture, why "healing" itself can become its own addiction, and — yes — an oddly moving experiment with ChatGPT as a journaling mirror. It all circles back to one question: are we allowed to be dreamers? And what does joy look like when it's not a reward for having it together, but the whole point?

This one doesn't resolve neatly. That's kind of the idea.

A podcast about Nike shoes co-founder Phil Knight,  sends Reuven into a full-blown crisis: what if work — even avodas Hashem , G-dly work— is supposed to feel like play? He walks into this farbrengen convinced Yiddishkeit runs on seriousness, guilt, and gritted teeth. Zakaria isn't having it. What follows is a raw back-and-forth about obligation vs. enjoyment, the Chassidim's original name (the Freilach - happy ones ), the king smiling in the Elul field, and whether your neshama/soul  is traumatized just for showing up in a body. Spoiler: the $500 Shabbos meatboard makes an appearance, and nobody comes out unscathed.

 Elul's trademark identity is — I am to my beloved, my beloved is to me. It can slip through  us without much thought. We repeat the formula — - arousal from below, arousal from above — but do we  feel what it means  to be to someone?

This episode gets uncomfortable. Someone can show up to shul daily throughout Elul and still, as the Frierdiker Rebbe puts it, be missing something essential — because the feeling of belonging never showed up alongside the effort. We talk marriage - what convinces a spouse they're loved - the archetypes that quietly move us without our noticing, the King who comes out to the field not to catch us in our mistakes but because that's what home can feel like. We talk  the Wizard of Oz, and whether "coming home" might get closer to teshuva than "becoming worthy" does. 

For anyone whose relationship to Elul has started to feel more like a checklist than a return.

Does believing "everything happens for a reason" make you more powerful — or turn you into a passenger in your own life? This episode cracks open Hashgacha Pratis (Divine Providence) and refuses to let it become spiritual Tylenol. Featuring the famous Rebbe/Rabbi Jonathan Sacks exchange — "one does not find himself in a situation, one places himself in a situation" — we ask the question : are we using Divine Providence to grow, or hiding behind it to stay in bed? Bitachon, free will, tzaddikim, and the birurim nobody signed up for. No easy answers. Just the real conversation.

I was  asked whether desperation is the right way to stand in front of G-d- Hashem — and the answer cracks open everything: why Kaddish praises G-d to the heavens and then says He's beyond all praise, why the Frierdiker Rebbe says humbleness  is reaching higher (not shrinking), and why your grocery store stocks 5,000 items your body never asked for. A conversation on bitachon, bracha, and what happens when we treat G-d like a vending machine.