You know the scene. Darkness falls. A hush settles over the gathered crowd. The rabbi intones: “The hour is nigh! Yom Kippur is upon us! Atone, turn your hearts toward righteousness, for today our fates are sealed. Who will live and who will die, who by fire, who by water, who by wild beasts?”

A pregnant pause. Your future hangs in the balance. Is there any way to tip the scales?

“Now, I’d like to tell you all about our capital campaign. There are pledge cards in the seat pockets in front of you…”

The High Holidays, when synagogues are at their fullest, offer a natural opportunity for annual fundraising appeals. It’s also the time of year when many Jews engage in cheshbon hanefesh, literally “soul-accounting,” meditating on what they’ve invested over the past year—in time, energy and resources—and how they want that to change in the year to come.

On this week’s episode of Not in Heaven, our rabbinic podcasters talk philanthropy. Is tzedakah purely monetary? What makes an effective High Holiday appeal? And while it might be more efficient to fundraise one $20,000 donation than 20 $1,000 donations, what does that mean for cultivating a culture of widespread giving?

As it says in Pirke Avot: “Without flour, there is no Torah. Without Torah, there is no flour.”

So, how do we raise the dough?

Avi Finegold: Yom Kippur is nigh, and that means that the Kol Nidrei appeal is right around the corner as well. This practice, which has a long history, has become an integral part of the Jewish calendar. Organizations are actively seeking donations to support their annual campaigns and raise funds for the year. Today, we take the time to examine this practice and how charity and philanthropy function in our communities and within ourselves. How do we donate?

How do communities manage competing priorities? And how can we all do better? Such a topic is worthy of the 10 Days of Teshuvah, and we hope it inspires you in some small way. I’m Avi Finegold, and along with Yedida Eisenstat and Matthew Leibl, we are Not in Heaven.

Matthew Leibl: How was your Rosh Hashanah, team? Shanah tovah. Happy New Year, friend.

Yedida Eisenstat: How was the energy, the turnout, the child programming?

Matthew Leibl: The child programming, we haven’t done the review yet, but there were like 35 kids and my kids were the worst, obviously, running around like crazy, but everyone else seemed to be occupied. We had 200-plus in the, I guess, the sanctuary room and the singers were fantastic. I still have this very strange feeling. It’s the fourth year we’ve done this.

I look out at this crowd of people and I literally know all of these people. Like I’ve known them all through different reasons. And they’ve all come together. It reminds me kind of that thing in the parashah.

Is it Nitzavim? Like Nitzavim’s around now where it’s like everybody’s standing together, the guy who does this job and the guy who does this job. And I look out in the crowd and I’m sure there’s people who love Israel and there’s people who really don’t love Israel and they’re sitting right near each other. And it’s a real cool cross-section of Winnipeg Jewish people.

And it just makes me very nervous to be up there, very stressful. And I’m thrilled as soon as it’s over, but it went really well. And I did a sermon on how I need to be a better listener. We all need to be better listeners.

Avi Finegold: Yedida, you did great. You were officially working also this year.

Yedida Eisenstat: A little bit, yeah. I gave a drashah and I taught a class later. I’m finding now in my, I guess, middle age, that as I approach hagim, there’s like a theme that emerges in how I’m relating to it. So that happened again and it, maybe like, maybe that used to be true and then I didn’t really get to think about the holidays because of all the crazy, but now I’m returning I think to a phase of life where I get to more spiritually and intellectually engage and it’s really nice to be back.

Matthew Leibl: What was the theme?

Yedida Eisenstat: I have always, I guess, because like I’m a modern person, thought about teshuvah, tefilah and tzedakah as individualistic actions and that like judgment is of Yedida Eisenstat as an individual or like as a familial unit. And so the good things that I go out of my way to do on the 10 days redound to me and my family unit. And I’m thinking a lot more about all of this as communal. Communal prayer, communal tzedakah, which we’re gonna talk about today, and communal introspection and repentance and how we need it and what it would take.

Matthew Leibl: You had a big exhale there. That was—powerful, though.

Yedida Eisenstat: That’s where I’m at. Tell us about yours.

Matthew Leibl: Wait, did you or did you not go to your wife’s Rosh Hashanah to hear her sermon? I know the answer, right?

Avi Finegold: I did not. Well, no, I also got asked a week and a half ago to lead Musaf at the shul. And so I did Musaf on day one and day two. So I couldn’t go to my wife’s shul.

Matthew Leibl: Can I nerd out for just one question?

Avi Finegold: Please.

Matthew Leibl: What’s your favourite part of Rosh Hashanah Musaf?

Avi Finegold: In terms of, like, singing? No.

Matthew Leibl: Is that where the part where the circus clowns enter? What was that?

Avi Finegold: It’s the Kitzvah at the end of Unetanneh Tokef. That’s what I hear her saying. Yeah, of course.

So it’s always, I mean, it’s obviously Unetanneh Tokef, both because it’s so—it’s so majestic in the content and deep. And for 10 years in Montreal, I had the world’s most glorious choir doing the most beautiful Unetanneh Tokef from beginning to end. It’s really—if you’ve never heard the Shaar Hashomayim choir do Unetanneh Tokef from beginning to end.

Matthew Leibl: That’s the Leonard Cohen choir, right?

Avi Finegold: Yeah, it’s on YouTube. You can go hear Unetanneh Tokef, them doing it. It’s like really, it’s transformative. It’s transcendent. It’s every possible superlative I can give.

Yedida Eisenstat: I will. Check this out.

Avi Finegold: The thing that hit me this year actually differently about— You know, Yedida was talking about the teshuvah. And I always say that that’s the only time in the entire service that teshuvah is mentioned on Rosh Hashanah. Rosh Hashanah is not about teshuvah, really. It’s about monarchy. It’s about the birthday of the world.

It’s about recognizing that we’re being judged, but we’re not being judged and therefore we have to apologize. You don’t go and say, I’m sorry, what can I do better when you’re standing trial? You’re like, your deeds are there and it’s the past year’s stuff that’s happening. It’s not about feeling bad for yourself. It’s just about standing in awe of the world that is our courtroom, the universe, and God, and all of that stuff.

If I have to say one thing for Musaf, it’s… Forget about… Those are all, they’re important, but they’re extraneous. It’s amazing how a song from only a thousand years ago has become the central thing of a holiday that is thousands of years old.

Matthew Leibl: Yeah, we do it. We do a very, very cool version. And then it goes into the B’Rosh Hashanah yikateivun, u’vYom Tzom Kippur yeihateimun, like that whole thing. I consider that whole thing to be there.

Avi Finegold: But it’s all part of it.

Matthew Leibl: Yeah, I mean, Leonard Cohen wrote “Who by Fire” about that too. We’ve sometimes looked at the words and sung that. I mean, it’s, yeah, it was what I talked about, like the listening part in my sermon that I was mentioning before, was the whole sound of the shofar followed by the sound of the delicate silence, right? The kol demamah comes after.

Avi Finegold: Silence is the most beautiful sound, but then there’s something else. And they say that that’s what that is. But I’m like, always think about the stillest, smallest sound, that even in the silence, there’s a voice, and then that’s what God is, right? It’s like—that’s my—so every line has imagery in that way in Unetanneh Tokef.

Matthew Leibl: Well said, that was cool.

Avi Finegold: Having covered the tefilah and having spoken about teshuvah, let’s move on to tzedakah, which is the topic that we want to talk about today. It’s the time of the year when many organizations have their annual campaign, often because the standard appeal time was Kol Nidrei, right? Hence the Kol Nidrei appeal, right? That’s the standard term for many people’s annual campaigns in shul, probably because that’s when the most people were in shul at any given time of the year. Look, The CJN is having our annual campaign right now.

You can donate online at thecjn.ca, right? Who by cash, who by cheque, who by money order, who by crypto. So it really gets us thinking about like, what is the nature of charity? What is the nature of tzedakah?

How do we think about what that looks like in terms of why that makes us better people, right? The idea that it changes an evil decree—tzedakah. And is that what we think about when we’re dealing with charity these days? Is that what we’re thinking about when we deal with philanthropy these days?

And what is the nature of all these Jewish communal organizations that are basically set up to think about charity and to think about charitable acts—all kind of govern how we are in today’s day and age as Jews. And so let’s take a moment to think about tzedakah, both in our personal lives and what we think about it in terms of community and how it’s being done. So I guess I’m gonna throw that out there and just ask maybe as a starting point, what do you guys see as your personal tzedakah? Do you say to yourself, I’m of the community and I give so much of my time anyway, so I don’t give as much?

Matthew Leibl: Mine are always the personal causes in my life. A cause that I often donate to a lot is ALS. I had an uncle who had ALS and he died like 14 years ago. And I’ve talked about that actually on Yom Kippur before. And so that’s usually like my big supporting cause, but you’re not talking about that.

You’re talking about Jewish stuff. And so like with Jewish stuff, I’ve never really thought about it because I think you touched on it. I’ve been the one doing the work. Like I started at the synagogue, I was 19. I never even really had a time to donate or think about donating back.

I was always kind of on the end of........

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