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Debbie Stone: Can Prayer Be Taught?

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SUMMARY

This episode is sponsored by Mosaica Press, whose books—including a range of titles on prayer—can be purchased for 18% off with the coupon code 18FORTY.

In this episode of the 18Forty Podcast, we talk to Dr. Debbie Stone, an educator of young people, about how she teaches prayer.

We also speak with David’s dear friend Brad Greenbaum about the experience of prayer in serious times of need—and with Rabbi Yaakov Glasser about how he helps people who are struggling in their spiritual lives. 

In this episode we discuss: 

  • What did Debbie learn about our relationship with prayer in the process of creating a siddur for teenagers?
  • How can educators better accommodate for the discomfort with tefillah often felt by newcomers? 
  • What is the role of “real estate” in prayer? 

Tune in to hear a conversation about all that goes into cultivating a practice of thankfulness within our communities.

Brad Greenbaum interview begins at 14:55. 

Debbie Stone interview begins at 33:55. 

Yaakov Glasser interview begins at 1:20:48.

Dr. Debbie Stone is an educator and lecturer. Dr. Stone serves as the Associate Head for Judaics at the Jewish Leadership Academy in Miami. She received her Doctorate in Education from Yeshiva University’s Azrieli Graduate School. Dr. Stone previously served as the associate director of education for NCSY, and authored the Koren NCSY Siddur, helping students learn and connect to prayer in Judaism.

References:

Three Steps Forward by Menachem Tenenbaum

The Musaf Prayer by Elchanan Adler

DMC: The Amidah by Ira Kosowsky

The Feigenbaum Teen Siddur by Yitzchak Feigenbaum

The Song of Shabbos by Yitzchok Alster

The Art of Tefillah by Shlomo David and Daniel Glanz

The Koren NCSY Siddur by Debbie Stone and Daniel Rose

In Her Place” by Yisroel Besser

Netiv Ha’Avodah 10 by the Maharal of Prague

David Bashevkin: 
Hello, and welcome to the 18Forty Podcast, where each month we explore a different topic balancing modern sensibilities with traditional sensitivities to give you new approaches to timeless Jewish ideas. I’m your host, David Bashevkin, and this month we’re exploring the topic of prayer and really what makes us human.

This episode is sponsored by Mosaica Press. Our friends at Mosaica have a ton of amazing books on prayer, which you can all check out on mosaicapress.com, M-O-S-A-I-C-A-P-R-E-S-S.com, mosaicapress.com. You’ll want to check it out. I want to give a special shout out to my dearest friend, Rabbi Menachem Tenenbaum, a colleague of mine at NCSY who just published a book on prayer with Mosaica. The book is called Three Steps Forward – Unlocking the Shemoneh Esrei and Connection with Hashem based on Rab Yonatán Eibenschutz. Sounds fascinating.

I’ve gotten a manuscript of the entire book. I have the actual book. I haven’t gotten a chance to read it yet. Menachem is a really dear friend, and I’m sure the book is absolutely fantastic. And if you check out Mosaica, they have so many other books on prayer that are worth checking out: The Musaf Prayer by Rabbi Elchanan Adler, Rosh Yeshiva at YU, DMC, Deep Meaningful Conversation by Rabbi Ira Kosowsky, who I actually know as well. They have The Feigenbaum Siddur, they have The Song of Shabbos, The Art of Tefillah, by Rabbi Shlomo David, a ton of great stuff that you want to check out. Thank you to our friends at Mosaica Press for their incredible work. Mosaicapress.com.

This podcast is part of a larger exploration of those big juicy Jewish ideas, so be sure to check out 18Forty.org. That’s 1-8-F-O-R-T-Y.org, where you can also find videos, articles, recommended readings, and weekly emails.

I think a question that every parent and educator asks regarding young kids, and there are always these sessions and parent workshops about it that I’ve seen at least, which is about helping kids learn how to daven. Can tefillah, can prayer be taught? And it’s almost always a question that we ask of younger children, as if adults have already figured this out. I actually think the more that I think about it, and especially through this series, I think it really depends on what aspect of prayer we are talking about. If it is, in fact, true that there are two problems that we have with prayer, there is the easy problem and there is the hard problem. Of course, neither of them are actually easy, but the easy problem is learning the basic words, the flow, how to pronounce, how to say everything, maybe even a little bit of the nusach, the tune with which you daven.

I think the easy problem of prayer can very much be taught. I was taught it in fourth grade. We would get tickets, we would go through meticulously every word of the Halelukahs. We would know them. I can pronounce them really well to this very day. Sometimes you hear people, they’re not really saying the words properly. I learned how to do that, and I think that is, so to speak, the easy problem of prayer, that if you get to it at a sufficiently young age in schools, showing up to shul at a young age and sitting through the parts that you’re able to sit through, that was always a challenge for me. But learning how to do that, I think is the easy problem. Prayer can very much be taught.

I think it is the hard problem of prayer, which is figuring out how the words of prayer can address our most basic, most essential parts of what makes us human, how to access our vulnerabilities when we come before Hakadosh Baruch Hu when we come before God at Shachris, Mincha and Maariv and be able to access that. That, in fact, I believe is really, really challenging to be taught.

What I have found where most people pick that up is either through really great experiential camp programming. I think to this day camp is where people learn how to mourn. It’s where people learn how to have Tisha B’av, and then they grow up and they spend the rest of their lives trying to access that realness, that solemness, that sadness that they were able to feel on that one day. They could spend their whole rest of their life learning to access that.

And unfortunately, I think when it comes to prayer, it’s almost impossible to teach somebody how to look at themselves with that sort of vulnerability. If you haven’t experienced it yourself, if you haven’t been through something or haven’t had the eyes to realize that you have been through something that really highlights your own humanity, then prayer can feel very, I hate to use this word, very ritualistic, which isn’t necessarily a bad thing. I think that there is a dignity and there can be a holiness, and part of the very structure of prayer is built on the premise that we’re not going to have all out wow intention kavanah every single time that we daven. We daven so regularly that we create these moments so when that vulnerability, when that realness, when authenticity of conversation actually rises to the surface, we have the muscle memory to actually allow it to enter.

But I do find that some people, their struggle, their sense of distance with prayer is actually part of a larger issue, which is really the hard problem of prayer, which is a distance from their very sense of self, their very humanity and all of the vulnerability and what wholeness and brokenness and all of that feels. Some people, that comes very naturally to and they embody that ani tefillah, that I am prayer itself, where their entire life and everything that they’ve been through and struggle with is always kind of bubbling right beneath the surface.

There’s this beautiful analogy that Reb Simcha Bunim talks about, Reb Simcha Bunim of Peshischa, who was Reb Tzadok Rebbe’s Rebbe. He was the Rebbe of the Izhbitza before he went to learn in Kotzk. Reb Simcha Bunim of Peshischa, and this always very much moved me, discusses this notion of Ani Tefilah of I am the prayer, I am embodying prayer itself. That sometimes you have fundraisers who maybe they come to your door, maybe they send you an email and they give you this beautiful laminated brochure. What are we collecting for? It’s a building. I’m running a marathon to raise money. They need to explain it to you and thank God they look like they’re doing great and they’re telling you this is what we are raising money for, this is what we need. And then there are other times in a person’s life where you get a knock at the door and you open up the door and you see somebody who’s totally han and their clothes might be tattered.

They look like they just finished crying. Their eyes are red, they don’t have such a fancy brochure, they’re not looking to build a building. When you see a person like that come at your door, you don’t ask them, what are you collecting for? What are you raising money for? Instinctively that they are raising money for themselves. And I think ultimately what Rav Simcha Bunim is saying is in that latter category that is the Ani Tefillah that sometimes we approach prayer and we’ve got our little brochure of what we’re raising money for. I started raising a little bit of money for 1840. I’m terrible at it, legitimately one of the worst, even though I believe in it very deeply. But the moment that I have to take out the brochure, so to speak and say, Hey, these are the projects we’re looking to build around, this is what we’re looking to enhance.

I know I’ve already lost the real prayer, the real coming before somebody. And they see instinctively from the way the person looks from what maybe the residue on their eyes, on their cheeks, right underneath, they’ve been crying, their closed, they’re closed of I am the prayer. What I’ve been through is the prayer, where I’m going is the prayer. And I think that that’s a more instinctive, a much deeper type of prayer that can be very hard to access in this button up world that we live in, where we are prized of having it together, keeping it together, and accessing your vulnerabilities in an intimate place, accessing your vulnerability, not on a podcast, not on Instagram, not on, I want to share this with the world, but accessing those vulnerabilities in the most private way. For some people it comes naturally to. And the hard problem is actually the easy problem because they don’t need reminders of what going through and what they’re dave for.

For other people that can be very hard. Things in their life, at least in the surface are going fantastic. And when they come before God, it’s always just a quick mincha. It’s checking a box and getting it together. And I think that there are people, and I’ve always been most moved by people who have it all together and you see they’re like they’re hanging on for their life. And I don’t think that they’re faking it. God forbid. It means that what we see at the surface in people’s lives, there’s always so much more happening and people are contending with things that we never reach the surface. That if that person is able to access it, and I’m thinking of somebody very specific who I grew up watching them davan, somebody who’s got a whole lot going for them. And I would watch them daven. I’d say, wow, this guy looks like he’s fighting for their life.

What could that be? And I think the hard problem of prayer is learning how to transmit that vulnerability, that insecurity that we contend with as part of our very humanity. Everyone is really able to access that. And I know for me what teaches me, and I’m using air quotes, how to pray, is accessing that vulnerability and finding ways to access that. I think the last time that I had a spontaneous prayer was actually right before Shavuos. This went around. A lot of people saw this, and I’m sorry for the long intro, you could skip this, it’ll be a little bit of a longer episode. But there was something that went around right before Shivu on social media. It was from one of these, all the different rabbis give the same answer to the same one question. And I think the question right before Shavuos appropriately enough was, who would you most like to have a chevrusa with?

And I read the question and thought to myself, I would love to learn with Rav Tzadok of Lublin, who I always mentioned. Maybe I would be a little bit fancier, go back, learn with my mother. She should live and be well. I always appreciate her thoughts and you know, always want the fancy answer. And I saw one answer that it went around that I hope everybody is hearing this for the second time. Stop me in my tracks. It was an answer from Rav Eitan Feiner who I know well, who grew up a few blocks away from me, very close with his younger brother Rabone. And he responded to tell you the truth, as a direct quote, anytime someone’s asked me this question, people know that I’m a true gruff fan, meaning the Vilna Gaon. I love the works of the gra. What I would first say is that I would love to learn with the Vilna Gaon.

When I think about it, that is not my final answer. My answer is, as people know, I’ve been married for 27 years. My wife and I have one child, a special son who is currently 15 years old and was born after 12 and a half years of infertility. He has many pictures with gedolei yisroel, he’s an adorable child, but he doesn’t speak, he can’t say an olive or a bayes. He’s seriously physically and cognitively impaired because of something that occurred shortly after birth regarding his amino acids. It is a miracle he’s alive today. The doctors told us he was going to die within three days. So if I asked the question of who I would like to have a chevrusa with and I could go with any one person in the entire world, it would be my son. If Hashem gave him a refuah shelema, he could talk.

The Vilna Gaon would be Mochel me, Moshe Rabbeinu would be Mochel me. But I would choose to learn with my precious son. And I read this and it’s astounding on multiple levels, but for me personally, when I read this, I started to dive in. I started to dave in because it had me reflect on my own vulnerabilities. I have a family, thank God they’re all healthy. And it is something that you rarely think about because when you say, oh, thank God everybody’s healthy, everybody should live and be well, you say it instinctively, but it doesn’t hit your heart in that very real way. And in a moment that your heart opens up and you’re able to reflect on what you do have. I was like overcome with a sense of very real instinctive Phi I, my life. My life is a prayer. My life needs to embody that gratitude, that realness, the vulnerability of what life entails.

And I think that all of prayer really is grappling with what being alive, what life in this world in fact feels like, is like with all of its vulnerability, with all of its gratitude, with all of its appreciation and learning how to transmit that and how to teach that feeling and how to teach that authenticity can be very, very challenging For me. I’ll be honest, I was less challenging. I was initiated into it. I wasn’t taught it, but I knew about the vulnerabilities. I knew about difficulties with mental health, difficulties with what life presents at a fairly young age that the instinctiveness of prayer, maybe the routine of prayer was more difficult for me. The every days mana showing up on time, that always came more difficult to me. But the more instinctive prayer of what really underlies our lives was always extraordinarily instinctive. And I try to cherish those moments and store them up.

When I have a moment of instinctive emotional prayer on what my life is, I really try to store them so I can access them so I can remember them through the more ritualistic routines of prayer itself. And that’s why before we get into our primary conversation, I want to stop a little bit. I have a friend in our community who actually listens to 1840. He reached out to me one of the kindest people in the world, his name is Brad Greenbaum. I asked him permission to use his name and Brad reached out to me my favorite reason why anybody would reach out to me. He said, I love your Torah ideas and I love your love of comedy. And we bonded over the very idiosyncratic comedy that I love. We spoke a little bit about, I think you should leave one of my favorite sketch comedy shows that season three has just dropped.

I’m not recommending it cause it is not all that appropriate, but it is quite hilarious and kind of deals with some of the absurdities of life. But the reason why specifically in this series I’m mentioning Brad, is because Brad has a very serious brain tumor and is somebody that connected with, and he’s connected with 1840 and he reached out and he shared with me something that he wrote. He is weak now because of all of the procedures and the medical diagnosis that he is grappling with. But he reached out and he wanted to share something. And I said, absolutely. This is somebody who is a part of that ani tefilah. I am the prayer, I am embodying the vulnerabilities that we try so desperately to access in our daily lives. Somebody who in his everyday life is living with that ani tefilah and I invited him over.

It is not always easy to hear because he does not have so much strength. And what privilege could be greater than to hear from somebody and their relationship with prayer itself, somebody who embodies everything that prayer is trying to reframe in what life is all about, the precariousness, the vulnerability. It is my absolute pleasure to introduce a brief conversation with Brad Greenbaum. I am sitting here with a dear friend, somebody whose prayer and relationship to prayer is I hope different than most anyone else because of what he’s going through in his life. Why don’t you introduce yourself?

Brad Greenbaum: 
Hi, my name’s Brad Greenbaum.

David Bashevkin: 
You’re a friend. That’s it. That’s all we need to know. Maybe to give context, what is going on in your life that you wrote, what you’re about to share right now?

Brad Greenbaum: 
Yeah, so right now I’ve been going through a very big health struggle. I was diagnosed with a brain tumor back 2019 right before Covid hit the world. And they’ve had three surgeries to remove one surgery to remove it for first it’s been recurring. I’ve gone through chemo treatments, I’ve gone through radiation treatments and whatever we seem to be due. So there’s been recurrences that we have to change the course of action. Recently, the last scan has shown a little more progression of the tumor and I’ve definitely had symptoms, wasn’t sure if it was a treatment or the tumor itself that have kind of definitely have kind of made me feel a little less safe and a little less, a lot of weakness in my limbs and extremities. So it’s been kind of a big struggle and kind of regaining strength and feeling safe and being able to do daily functions.

David Bashevkin: 
And speaking, just so it’s clear to our listeners, has also become significantly

Brad Greenbaum: 
More difficult. Yes, speaking has been a little bit rougher. Just as my left side has gotten weak, it made its way up my face as well to my mouth and speech.

David Bashevkin: 
I think what you shared with me and you were so gracious to even want to share it with our audience, you wrote an essay that I found incredibly moving about prayer itself.

Brad Greenbaum: 
Yeah, so I wrote this as a personal prayer given everything I’ve been going through the last few weeks, month. So I wrote I struggle with so many heavy thoughts that weigh me down as my body is trying to heal and regain some of the feeling it’s lost. These thoughts and feelings are getting a little too heavy to hold. Of course I feel fear for my life, but I fear for the lives of those around me. I pray to be better and I know so many people, better people than me who are praying on my behalf mitzvot are being performed on my behalf. Yet I remain sick and weak with scans showing progression after scan, showing progression. So I sit here asking the following questions of, as I write this, motzei shabbos , I spent the last two weeks for shalosh seduos bawling my eyes out. As I sang gam ki elech bgay tzalmaves lo ira ra ki ata imadi, how can I fear evil?

If you are with me, one memory I have from nursery is singing a Hanukkah song with my friend Ricco. I’m yehuda hamacabi, I’ve come to save the Jews with a aside. There’s no way we can lose as a 37-year-old man, I still feel that to be true. But Hashem, are you on my side? Should I fear no evil? Is there no way we can lose? the chazan comes before you on Rosh hashana and yom Kippur saying they’re not worthy of your presence in front of, to be pleading on behalf of the congregation. And it makes me wonder, are my prayers is not worthy for my refuah, are those who are praying and doing these photo on my behalf not worthy. The chazan begs for your 13 attributes of me mercy to show us, to view us as worthy. Can I be worthy? My eight-year-old son prays for me.

He asks where to insert my name in tefillot. Is he not worthy of his tefillot for a healthy dad to be answered? Your’re approaching Shavuot where Hashem was revealed to us at Sinai. But right now the revelation is so opaque. My observance has suffered because I literally can’t practice. I can’t feel my arms so can’t do tefillin. It’s hard for me to get to shul. But what worries me is my disconnect. As Shabbat was coming to a close, I started wondering why was I still observing? I was worded alone and I’m still struggling to fill God’s presence with me as my daughter complained of a similar boredom. How could I disagree? Why weren’t we on our phones? And then while talking to my son about avrahams nisyanos , I wonder, is this mine? And then my failing and I continued to cry out for Hashem to be with me because I think I believe and I want that belief to be strengthened for my family and me. My emotions are a mess, is keeping them in check. My test, it took me a long time to get angry. Not sure I am there yet, but I’m on my way. I try to stay positive and thankful in times of greater practice. I love saying modim, but as it becomes harder to find those things, to be thankful for, my emotions get angrier and more negative not where I want to be, but is this the test and then my failing?

David Bashevkin: 
It’s an incredible tefila to me, the very questions that you’re asking. There’s this beautiful piece from rabbi nachman, even for those who aren’t so well versed in the Torahs of Rabbi Nachman where Rabbi Nachman says that the ultimate prayer in a sense is the question of ayeh makom kivodo is the very confrontation with the abyss of life where nothing makes sense and is difficult to wrap your arms around it and to really understand why am I going through this? It doesn’t seem like there’s any God here. And crying out ayeh makom kivodo, where is your honor, where is your glory? Where is your presence in all of this? I’m curious for you reflecting on what you went through and what you’re still going through very much now with the family, with children, has prayer become, and when I say prayer, I don’t mean showing up to shul for shahris. I mean having a conversation that there is something outside of my life, beyond myself that I can be in dialogue with. Has prayer become easier or harder? Has it changed?

Brad Greenbaum: 
I would definitely say it’s changed. I think in a way it’s become easier because in a way, when I am able to say the words and reflect on the words, there’s meaning there. I mean, I remember long time ago learning about this, how to move to shift the way a little bit for prayer, but that you know, should cry on Tisha bav. And if you can’t muster up tears for the destruction of the temple, you should muster up the tears that you’re not connected enough to muster up the tears about the Sure. And what’s kind of easier now and my tefila is to actually be able to muster up the tears, my own tears about my own priors and have that kavana in a way that maybe there was a disconnect.

David Bashevkin: 
When you Daven, are you focused exclusively on an intervention that God should heal you? What are you thinking about?

Brad Greenbaum: 
I mean, I think what I still try you to take a look at the words like daven in When I’m daveningI think I see unfortunately it’s not just me that is going through health issues and there’s so many others. So when I talk about probably about refuah, I do probably about everyone who’s in need of refuah. And also all I talk about always loved saying modim and always I’ve been taught the importance, let

David Bashevkin: 
Me interrupt you. I’m so sorry. It’s so moving. You would think that somebody in your situation, you’ve been living with a brain tumor for multiple years, you would think the hardest prayer for you to say is modim. Why do you saying modim? I

Brad Greenbaum: 
Really have felt that through all of this, it’s so important to see the positive and when you see the positive, and it’s coming from Hashem and I think I was talking to a friend also about modim. Modim. It’s just an admission, admission of the higher power. And that’s kind of where it resonates because in the end right now it’s had three successful surgeries. There are things to be thankful for even though it’s not all clear and it could be a battle forever and hopefully for a very long time. But still, there’s always things to be thankful for and but worrying me is how the stretch I need to get there. Whereas after my first surgery, I remember waking up from my first surgery feeling like this incredible sense of gratitude and rebirth, new life and this is incre. And now those kind of bits of kind of glory has been a little more fleeting and that becomes a little more challenging to find those morsels of hodah.

David Bashevkin: 
I’m curious, I want to speak delicately. You’re very aware of what the stakes of this illness is. I’m curious if there’s a fear. There’s like, I’m afraid, what is the inner experience, the way that you reflect on your life and what you have? I’m curious if there is a sense of trepidation and afraidness.

Brad Greenbaum: 
Yes, there definitely is. Because also as just so much unknown right now, and I think one of the other things that I remember about confronting my first surgery was I was very scared. What was I scared about? None of the actual surgery of the anesthesiologist.

David Bashevkin: 
It is

Brad Greenbaum: 
Scary. And I think one of, as it was explained to me, and I have friends that are doctors, I have friends that are anesthesiologists that they kind of put you under and then they’re kind of basic controlling you. They’re like breathing for you. They’re doing everything for you. So you could kind of be in this state where they can operate on you. And it’s kind of a real life example of how we have to give away or we’re not in control and you know, don’t really always feel that hashems in control and there’s no real kind of, I guess real life analog where you’re like, but here it was. And it was kind of a very powerful emotion going in to it being like, okay, I have to just seed control to a higher power this time with an anesthesiologist, but in the real world it’s hashem. Yeah. And yeah, there’s fear because again, the fear is still there because I’m still seeding the control of my life to Hashem. Do you

David Bashevkin: 
Think you’ve become more religiously sensitive through this or less? I think most people when they go through something like this, I guess in your own head, and God forbid one should have to go through what you’re going through in the strength that you have, is frankly deeply inspiring. Even though we initially connected over our mutual love for comedy and not anything so theologically profound. But I’m curious if this experience, did you always speak so religiously when we first met? I was actually taken aback. You wanted to learn together and study and were you always like that or is the confrontation with vulnerability, does that change the way you look at life? I

Brad Greenbaum: 
I mean I think I’ve always been religious, spiritual. I mean it’s hard. I think the way and my prior kind of mentioned that it’s making me nervous is leads some disconnect or some like that. I don’t want this. Again, when I think of maybe some of that modim that I’m thankful for is maybe that reconceptualization of where religion is important to me and I just don’t want to be sitting there towards the end of chais wondering why I’m still doing this. Back in the day, end of Shabbos to me is one of the most whole, the holiest time. That’s why I saying, you knows, zmiros or shalosh seduos.

David Bashevkin: 
It’s fascinating because you kind of went to pretty centrist, standard, modern Orthodox schools. I don’t have to go through your background, but you do have a deeply ingrained, instinctive spirituality that I find really uplifting. You mentioned the appreciation you have for other people davening on your behalf. And I’ve done this before, I’ve submitted my name for other people to daven for me, not during a physical illness. And it’s always strange to see your own name on the Cholim list. And I’m curious for you, because I’ve struggled with this on davening on behalf of other people, especially people I don’t know. I have a hard time davening for just a name and I don’t know the person. My understanding of davening does not, I wouldn’t say it doesn’t allow, but it doesn’t give enough context for me to really daven bkavana and with intentionality for just a name. But I’m curious for you, as a choleh speaking, what does it mean for you to know that other people are davening on your behalf?

Brad Greenbaum: 
For a while it meant a lot because, I mean, again, I think that some of my struggles with, not religion per se, is practice. Is kind of like, it’s hard. We alluded to these centrist institutions that I kind of grew up going to, but I probably should put quotes on going to. I didn’t go minyan all that often in school. A lot of detention, a lot of missing class, a lot of, I was just like that kind of like…

Because it was hard. It was hard for me to get up and do everything, learn what you’re supposed to do. But I was always in awe and very impressed with my friends and I have a lot of friends who went that route and are rabbis and teachers and everything and I’m amazed at what they do and how important it is what they’re doing. And to me, when these people who have done stuff with their lives that I could only dream of doing, it makes me feel good that I have, I alluded to I mean, obviously I speak a lot of what it means to be worthy, but I feel like these are, I have advocates that are worthy, that’ll be viewed in the right light.

David Bashevkin: 
It’s a very sweet sentiment. It’s very moving. You’ve always had this great esteem for your friends and your friend group. We only met two years ago, a year ago. We didn’t really know each other all that well. I guess my final question, who taught you how to daven and do you think that beyond experiencing vulnerability in itself, can it even be taught or is it something that you kind of have to go through to have this perspective?

Brad Greenbaum: 
So I’ll say that obviously any kind of person who grew up like myself, obviously siddur play, you got your siddur you learn in school, but I actually happened to be the son of a chazzan and so my father would, at his parents’ shul would daven rosh hashana yom kippur, and that was always very inspiring to me. And then my mother grew up kind of learning, she went to public school but learned through her local…

David Bashevkin: 
Talmud Torah, or yeah.

Brad Greenbaum: 
Talmud Torah. I know, interestingly enough, some of the rabbis and her mentors became prominent rabbis in institutions that I eventually went to. And she would always talk about how she learned to pray through these and how even just benching out loud was so meaningful to her because it’s not something that she grew up with in the house or in school, but had these outside opportunities.

And my parents always showed, I think, always showed me how important tefillah and practice was to them. And then even as, like I said, I was a very, lazy, lazy, lazy, sleep in on Shabbos. Not necessarily maybe ideal time to get to shul was right before musaf, but I always saw the dedication from my father and my mother and my grandparents, or my father’s parents about getting to shul on time and how they valued it. And then as my father grew older and obviously his parents passed away and he was then had to go say khaddish and he made a commitment. These have been very inspirational things that I’ve seen as to how important.

David Bashevkin: 
Is there a specific line of davening, not a full prayer, but a line that you find yourself coming back towards or thinking about or using as almost like a meditative practice to think about?

Brad Greenbaum: 
That’s a really actually good question and I have a couple. For a while, one thing I’ll say is, and I don’t love to do so much by heart, so I like to read more, but when I’m in my MRI, I’ll say shir hamaalos esay eynei el haharim.

David Bashevkin: 
Inside the MRI?

Brad Greenbaum: 
Yeah, in the MRI machine. And I’m pretty sure actually I walk down my aisle.

David Bashevkin: 
That’s a beautiful way. And continue looking upwards, we’re looking up with you, we’re davening with you. And I cannot thank you enough for speaking with me today.

The essay that he sent me was so beautiful. It’s entitled A Personal Prayer. More than anything else that he couched this as a personal prayer to me is everything that the hard problem of prayer is trying to cultivate within us, which is very conversational, contending with those emotions and feelings of being alive that we’re not inanimate matter just sitting listlessly. We’re different than a chair and a table and a book. But we have an interiority that gives life all of its richness, but all of its scariness and anxiety and learning how to contend with our interiority, which is the hard problem of consciousness.

We didn’t need this interiority. Life would’ve made a lot more sense scientifically without it, but it’s that very interiority that gives us that hard problem of prayer. Of learning how to view ourselves not as objects, but as subjects with a rich interior world, which is filled with all sorts of different emotions that we try to bring order to through the act of prayer as we come before God as subjects rather than objects and say the interiority of my life is not an accident of science and evolution, but the interiority of my life is actually the most divine, perhaps that divine duet, in the words of Sam Lebens, that we continue to utter.

And that’s part of why teaching prayer can be so hard and so easy. That’s why I wanted to reach out to a friend who literally has spent a great deal of time actually teaching prayer. Her name is Debbie Stone. She was a colleague of mine in NCSY. We are old, old friends. She’s originally from London and she published the NCSY siddur, a fantastic siddur published by Koren. She did a ton of work on prayer. She did a entire prayer cohort with other educators. It is my absolute pleasure to introduce our conversation with Debbie Stone. Really a pleasure to be speaking with my friend Debbie Stone.

Debbie Stone: 
Hi Dovid, it’s great to talk again. It’s far and few between when we get to chat, so I’m excited about this.

David Bashevkin: 
It is far and few between, unfortunately. And I wanted to begin, you are the author, you maybe co-edited a teen siddur. There are two editions, there’s an NCSY edition and there’s like an edition that is used in camps and in shuls. What’s the name of the siddur? Remind me.

Debbie Stone: 
We went through so many iterations of what we’re calling it, but there’s actually three versions. It started with the aviv siddur, which is part of a series, of the Magerman series of developmentally appropriate siddurim that children graduate from as they work their way through tefilla and maturity. We worked in partnership with Koren and Dr. Daniel Rose, who was the author on the side of Koren. But what became very clear was that NCSY’s partnership was only as useful to us as it was to have shabbos involved, and originally it was a weekday siddur. So the NCSY version became the shabbos inclusive package, the whole siddur, which includes shabbos and other tefillas that you need for shabbos and yom tov.

David Bashevkin: 
Because most of the NCSY education, just to make it clear, is taking place on these weekend Shabbaton retreats.

Debbie Stone: 
Exactly.

David Bashevkin: 
We’re not running that many events on a Tuesday morning. That’s not the sweet spot for NCSY.

Debbie Stone: 
No, it’s not the sweet spot. No. So clearly shabbos and yom tov was a priority to make sure that that was in. And then in the UK, they have their own slightly varied approach. The Nusach is slightly different. Obviously the pictures and the spelling and the references, I can speak to that perfectly from being a cousin from another country and suffering from a language difference. So there are three versions of it, but all in all, the bulk of it is the same.

David Bashevkin: 
And it’s become known as the NCSY siddur generously sponsored by the Rothner family from Chicago and it’s really incredible. I’m wondering, we were working together when you first began working on the siddur, and I remember initially when you first started, I had this haunting quote that a teacher in Yeshiva when I was in had told me. I know a very notable person who wrote a book on prayer and he said that ever since I wrote a book on prayer, I have struggled to daven myself. Which I always took to mean that there’s a deep sense of imposter syndrome to cart yourself out forward and be like, let me teach you how to daven. So what is unique about the approach to teaching specifically teenagers how to daven? What did you emphasize in that siddur and what did it teach you really about teen approach to tefilla?

Debbie Stone: 
The unique approach of the siddur is to try and speak to the person who’s reading the siddur and invite them to personalize and invite them to ask themselves the questions. It’s not to tell them what to think, it’s to ask them to think about how they want to think about things. So for example, in the siddur there are reflective questions and it asks the person who’s davening to think about what they would feel or how they would see something.
There’s almost nothing in the siddur that’s directive. It’s all about being introspective and thinking around an issue, and that’s really all that teenagers are really doing. They’re self-individuating, they’re trying to find their own space in the world, they’re trying to look around and see what’s out there and see what’s genuine and see what’s real, and they’re also trying to find themselves. And so the siddur had to find that sweet spot where you can show them things out there but not tell them, and not force anything, but really try and give opportunities for connection, for reflection, for inspiration. But it wasn’t so much about direction, it was much more about trying to give them spaces to look.

David Bashevkin: 
You wrote the siddur, you were not a teenager at the time. I’m curious if there are any reflections that have crept into your own davening. We always around Pesach time when people are getting ready for Passover, there’re always these classes, how to make the Seder come alive for teenagers, as if the adults have it figured out, which we very much do not. And I think a lot of times when we direct things towards teens’ education, it almost gives an adult an excuse to reimagine and build anew their own relationship with prayer. I’m curious if there were any reflections or even methodologies in the siddur that you wrote that ended up creeping into your approach to prayer.

Debbie Stone: 
It’s funny. Thinking back on it with a couple of years distance, I think there was a strong sense of distance from myself and what I was working on. Because of that imposter syndrome that you mentioned before, there were times where I was like, this can’t be about me. This can’t be what I’m telling people, because I can’t tell people this. I don’t do this well enough to tell anyone about this. I was hopeful that some of the things that were inspirational to me would be inspirational to others, being someone that also struggles with davening, with no secret about it. It’s not a shameful thing to say. I struggle with davening. My name is Debbie Stone and I struggle with davening.

And the things that crept in I think were really having to find those connections. There were some tefillas that I left out and came back to later because I didn’t have anything for that one or I had to find someone who had something meaningful. I remember I showed it to one of the kind people who went through page-by-page, one of our editors, one of our content editors, and I showed them my page or my ideas for mizmor shir chanukas habayis ldavid.

David Bashevkin: 
That’s one of the prayers, just to translate. It’s one of the opening prayers in the morning service where we kind of introduce and it’s a prayer of newness and renewal in a way, when they first built the temple.

Debbie Stone: 
Yeah. And that’s kind of where I was going. I was going with looking at the chanukas habayis and looking at the dedication of the temple and he said to me, “Really? This is where you went? I didn’t think of that at all.” He said, “This was a tefilla that took me through some very difficult times,” and the words that he focused on was coming out through the depths of a whole and it gave me a different perspective and I think that’s where I had to go with it. I mean, we went in different directions, but talking to people, struggling through trying to connect to certain tefilla and not being able to, and actually having to have the humility and the ability to go to different people and say, “What do you see in this one? Because I’m coming out with nothing today or this week,” really helped me and it helped the siddur because it became richer from having so many different voices and approaches.

David Bashevkin: 
One thing that you did almost concurrent with your work on the teen NCSY siddur was you had these cohorts that you would organize together. I think they were mostly via Zoom, though I think there may have been one or two in-person conferences where you would bring together educators who are involved in either prayer services or actual classes on prayer in their school. And I’m curious just generally before we dive into specifics about some of the exercises that you did. Are you a fan of having a class on prayer in Jewish schools? Is that a class that we should be having more of?

Debbie Stone: 
Yes. One of the things I learned with these cohorts, which was bringing together in a way that I don’t think Jewish schools are able to come together in such a vulnerable way and say, “This is hard. I’m not doing well.” We had rooms of people where they were all very vulnerable and open and saying, “We’re struggling. Let’s talk about this.” Whereas many times day schools are really happy to jump in and say what they’re doing fantastically. So this was a real space of vulnerability.

But in answer to your question, a lot of times people said there’s no place in the curriculum to do that. We don’t have time to dedicate a class to tefilla B or tefilla, we don’t have time. So we’ll pepper it in in the davening time of the day. I’m working in a new venture now, I’m in a school called JLA in Miami. It’s opening in August.

David Bashevkin: 
Are you plugging your new school, Debbie Stone?

Debbie Stone: 
I’m not plugging my school. You know, I’m plugging my school a little bit, but I am plugging something really important. In our seventh grade curriculum, we felt strongly enough to make sure there is a class on tefilla. It’s a core class and we felt that it’s really, really important. I think it’s going to be a really popular class because all our classes are by choice. But yeah, I really do think it needs to be done. I don’t think you can do all the work that needs to happen to talk about tefilla, to teach about tefilla, to explore tefilla in the time that we have for tefilla in school.

David Bashevkin: 
See, it’s so interesting. I’ll be honest with you. My fourth grade rebbe in South Shore gave a tefilla class which was exclusively, he would give time exclusively to how to pronounce the words. He said, “If you don’t learn now, you will be mispronouncing these words for the rest of your life,” and that absolutely stuck with me. And in fifth grade and in sixth grade we had a prayer class that worked more on the translation and the meaning of the word. And I’m going to be honest, I thought those classes were a waste of time.

And I think a lot of the work that you’ve done on prayer actually comes as a corrective to this. I think if you’re going to teach prayer, it’s not a text in the same way a text of a Mishnah or the Chumash or any other text of rabbinics is, because really the ultimate text of prayer is the self, is the way you examine yourself. And especially when you’re in seventh grade, I feel like that could be a very young time to really delve into self-exploration. For the average kid, you could get stuck in a very childish mindset for prayer, and what prayer really needs to be is deeply experiential.

That’s what I found in my own life, where you get in touch with that instinctive prayer, the sense of your own vulnerability and inadequacy. I’m curious for your seventh grade, and I know you were a master and are a master experiential educator, and I want to talk about some of the programs that you’ve ran that helped me look at prayer in a new light. But I’m just curious for a moment, push back a little bit. What can you teach a seventh grader about prayer? Are you going through word-by-word and explaining what the words mean?

Debbie Stone: 
No, it’s not word-by-word. We are doing things much more thematically and we want to give context to particular tefillas in general. So the curriculum is built in a way that kind of gives context and gives space for understanding why certain things are in the siddur in the first place. What are they trying to achieve, the different aspects of prayer. You’re right, seventh grade is straddling a place where you go from the elementary education, which is you kind of have to indoctrinate. Forgive me a little bit, but when they’re little, and it’s a conversation I’m going to have over Shavuos, but how much of our education system is indoctrination and how okay are we with that?

But I think we all know that when they’re little babies, tiny ones, you get them to repeat after me. You teach them to daven them by saying, “baruch, repeat after me.” We’re past that by sixth, fifth, sixth, seventh grade. Either they can do it or they have to learn how to do it because they didn’t get the background. By seventh grade, you’re starting to become a human, you’re starting to become a person. You are looking for context in what’s going on. You’re looking to say, “Why is this here? Why am I here?” It doesn’t have to be the biggest existential question of where am I in the universe and where am I going and what am I doing?

But I think at the seventh grade level, minimally the context of why is this here and why do we say this and what is the relationship between this and you see this tefilla actually comes from this part of Chumash and this was the context of when this was said, and this is the centrality of this particular prayer or whatever it is that we’re saying. Seventh grade for us when we were thinking about this was a time where that begins. It’s not to say tefilla education ends by any means, but it starts at least when they start our question, some of those things in that place.

David Bashevkin: 
Let’s talk a little bit about some of the experiential programs because it’s so not my style, in a way, it’s not your style either. We kind of always have the background whispers of the inner cynic inside of us. But I one time watched you run a prayer workshop for NCSY advisors that I found breathtaking in its creativity. You essentially set up a mock shul, like a mock synagogue and wanted to explain why some people find tefilla so grating and difficult. You’re basically talking to an audience of people who are going out there, about to become teen educators, they themselves are in college. They’re all fired up, they just came back from their year in seminary or Yeshiva, and you tried to recreate reminding them why the struggle is so real and some of the exercises you did I thought were brilliant. Take me through. I remember sitting on the outside, I was probably looking in jealously of all the attention that you were getting.

Debbie Stone: 
Well, you’ll remember I had to behave quite shamelessly to make it work. And so there was probably a jealousy but also a little bit of laughter at my expense and I’ll forgive you for it. You’re right. What I did was I set up the room to reflect all the bad things that can happen in a shul. So for example, the women’s section was an eighth of the size of the space with a mechitza that was built out of bulletproof tables and chairs piled on top of each other that made no sense at all.

David Bashevkin: 
Like wobbling back and forth.

Debbie Stone: 
Wobbling precariously. You never know. There was no access to the women’s space, you had to walk through the men’s space in order to get to the women’s space. Or the other way around, or both, I don’t remember. There was a sign that said men and not men as opposed to men and women.

David Bashevkin: 
That’s a great touch. Men and not men.

Debbie Stone: 
It was great. I think that’s what someone came over to me after and they’re like, “Really? You went all the way?” I’m like, “All the way my friend, all the way.” There were not enough seats on purpose. There were not enough seats.

David Bashevkin: 
I just want to pause right there, because it’s a sensitivity I never appreciated. There was actually a somewhat controversial article by Yisroel Besser in Mishpacha Magazine many, many years ago where he said he appreciated some of the difficulty of mechitza as a practice the first time that he went to his daughter’s Bais Yaakov chumash party, which was mostly mothers and the men were kind of hurdled in behind the mechitza. There was not enough space for them, and he’s like, “Oh, this can be difficult. This can be very real.” When people are complaining about this, it’s not necessarily because they hate their halachic practice or their halachic tradition.

Debbie Stone: 
No, it’s genuinely uncomfortable.

David Bashevkin: 
And I remember growing up in the shul that I grew up in, there was a practice on Friday nights for the men to daven in the women’s section. And I just remember to this day the look that guys would give when a woman would actually show up to shul to her own section, she’s only got, and they would just be like, “You again. Really? We got to move now?” Nobody ever said anything, but it was so disgruntled and there was actually an incident that I remember once, I’m afraid to bring it up because I suspect she or her husband may listen to this, but somebody one time showed up for a shacharis davening, a woman showed up for shacharis davening in our shul. I come from a little bit more of a Yeshiva community.

Debbie Stone: 
During the week, I assume you mean.

David Bashevkin: 
Yeah, during the week where women do not usually show up to shul and there was a little bit of an uproar that people had to move out of the women’s section. It was a very painful chillul hashem to watch. I genuinely don’t want to relive it, but you kind of showed them that sensitivity of what that looks like. What Moish Bane has said to me before, that in corporate offices when you finish a meeting and then it’s time to daven mincha, give it a beat. Give it a moment before you just bang on the table and say ashrei. Look around, maybe there are women in the room who either need to daven and would like to be with a mechitza or want to leave the room. But this sense, okay, get out now, grab your sushi, get out, it could lead to a very grating experience. What else did you do? Because you had an improv component?

Debbie Stone: 
Yeah, we did. We had these little booklets which were to represent siddurim. They looked more like hymn books, to be honest. And in them were Shakespearean sonnets, a selection of Shakespearean sonnets, which I am absolutely no expert in, but I just found a bunch and in nice italics, tiny little italics over various different words in the sonnet were instructions. Instructions for the reader. Stand up, sit down, twirl around six times, put your hand on your head, stick your tongue out, walk to the back of the room, chant something loudly, say whatever’s in your head. All over the sonnets, and multiples of them.

And what we did was gathered everyone into the room. I was the leader, and this is the shameless part. I stood at the front, which is also awkward because we don’t typically have female leaders in our tradition of davening. And I said, right, everyone. And I shepherded everyone in and I made a point of being extra mean to anyone who came in late. I’m like, “You’re late. Come on in. Hurry up.” And I said, “I’m the leader. I will follow the leader part of the sonnet. You are the crowd. You will do the crowd part. Let’s go.” And credit to them, because NCSY advisors are just the best. They went with it. They could have left me hanging at the front there looking like a complete idiot, but they didn’t.

David Bashevkin: 
But they looked like idiots with you.

Debbie Stone: 
They looked like idiots with me. And that left you at the back laughing, so there you go. And I read, as the leader did, reading Shakespeare in my British accent, but poorly, I will say. And they got involved and one or two took the plunge, but they got involved and they were jumping around the room and following. There were some who got involved and understood what we were doing and went with the improv. There were a few of them who were looking around going, what the heck is going on here? I don’t know where I am and I don’t know what planet I’m on.

David Bashevkin: 
But that’s kind of what you were trying to do.

Debbie Stone: 
That was the goal, for sure.

David Bashevkin: 
You’re trying to recreate the foreignness that prayer can sometimes evoke in me.

Debbie Stone: 
Yeah, and they were the ones who came in late and were not treated well and then were also looking around with no introduction because we were in the middle, we weren’t stopping to give the instructions again, and either got involved or didn’t, and some left. I remember one person who didn’t quite get where I was going with this, they didn’t get the mashal, the methodology, the style. She was very offended by something I said or did or the signage and she got up and walked out and I was like, great.

David Bashevkin: 
Exactly.

Debbie Stone: 
But what we did at the end was the most important, because the most important part wasn’t just the experience, it was the debrief. And what I asked everyone to do once we finished was walk around to four corners of the room where there were different prompts to ask about people’s feelings to debrief how they felt. Mostly negatively, obviously, but the design was to get people to really articulate, not just feel it, but really articulate what went wrong or what was happening for them and they themselves then made the connections. They themselves then said the uncomfortability, the foreignness, the lack of feeling like I knew what I was doing, the fact that it’s in a language that I actually speak, but I don’t understand. This is English and I don’t understand this English. We’ve got sometimes native Hebrew speakers who speak at a rip and they look at siddur and they’re like, this is not Hebrew. This is something else, I don’t know what this is.

The debrief was very, very powerful because what it did was it gave this group of people, this group of budding educators, a sense of the next time I walk into a shul and I try and grab some new teen who’s never been here before and just shove them into this to feel the experience, I need to take pause and think about what the most uncomfortable thing could be for them and just give them a moment and try and encourage them and try and invite them and try and be sensitive to the fact that this is hard.

David Bashevkin: 
I think one of the things that you uncovered, which always stuck for me, was the role of real estate in prayer. And by real estate, I don’t mean doing a real estate deal in the back of shul, which I’m sure happens in some places of worship. But what I mean is the need for the actual physical space. The sense of feeling cramped inside of a shul.

I like to daven very early, particularly on shabbos, where it gets crowded. I never, ever, ever daven in the main minyan, because I know I need the space. And I remember when I would go to Israel, there was a rav named Rav Bloy, who was a world-renowned posek, a decider of Jewish law. I think he wrote a set of works, and he used to walk up and down during pesukei d’zimra, those early morning prayers. And sometimes he would even forget, he would take his shoes off and he forgot where his shoes were sometimes. He needed to move around and one or two times I ever daven in the same minyan Rev Avrum Schorr, I’m sure I noticed he does the same thing. He would pace up and down the aisles like anxiously as if he was getting ready for a big phone call or a big conversation.

David Bashevkin: 
I was getting ready for a big phone call or a big conversation during those early morning prayers. And I said like, I’m not crazy. I need to move around, I need the space. I can’t stay seated like I’m on a six hour flight. The only other place where I’m forced to sit in place for so long. I’m curious, that exercise kind of mirrors the difficulties that people have with prayer. I’m wondering if in the cohort, if there were specific methodologies or programs that helped highlight in a positive sense, what does work to illuminate, particularly for teens, how to get in touch with that vulnerability. Either what you ran yourself or what you gleaned from those cohorts of educators that you were working with.

Debbie Stone: 
Yeah. One of the most powerful things always with teens, and people, is to give them choice and to give them a sense of autonomy. I saw it myself. We did some traveling around the cohorts as well to see, not just to hear about it, but to see, which was amazing. Shalhevet high school in LA do an incredible job of creating a space for the teens to make their own minyan. You were mentioning the rabbi who walks around in schools. It’s a terrible, in my opinion, a terrible Minhag of educators where they’re not walking around for their Karvanah, they’re walking around to police the situation that is going on in davening. And this minyan was a non-teacher minyan. It was completely self-governed by the students. It’s their hashkama minyan, which means it happens before school starts.

You have to be there on time by their own laws. And we were invited to join as guests and it was just wonderful to see them just run it their own way, welcoming us, doing everything you want to see done right in a minyan, going at a pretty decently fast pace. But there was zero tolerance for talking, of their own own decision. They ran it well. They managed davening. I think sometimes though, the question also has to be what are the goals? We are talking about davening in a very introspective, a way that you have to become in touch with yourself and become someone who understands the role of Tefilat. I think that is one of the goals of Tefilat in schools.

I also think sometimes you need to separate out what the goals are, and it might be different for different kids, but for some kids or for some schools, having a community where people feel part of a community, that they can be in that space and feel part of it and feel connected and feel close, and then they don’t necessarily fully understand the words. And there isn’t necessarily this big spiritual interpersonal inter-god connection. It’s not that, that’s not what it is, but they feel part of a Kehilla. They go there when something happens in the community and they’re together. They know how to participate. In other schools, the goals might be that the kids know how. They know how to respond, they know how to lead, they know how to do dovening, that it can show up in a Chabad in Bangkok and participate.

That they can show up, in Eretz Yisrael and knows any place that they’re singing the same tunes and they’re singing the same songs and that they can do the same bowing motions because they’re part of something, and they learned how to do it. And in other schools and in other places, and sometimes you have to balance those goals, the goals are to make someone an introspective, prayerful, soulful person. And sometimes, and I say this gently, I don’t know that all those goals can come together in the same moments. Sometimes you have to choose when you want those goals to happen, and sometimes it has to be in different communities at different times, at different grades, at different levels.

But this very soulful, spiritual thing is a beautiful thing. Very often schools were finding themselves having to move away from traditional davening in order to achieve it. So there were schools that were doing amazing things like having a completely silent minyan. So there was no talking and there was no noise. That it was so intentional that a child who left the room lifted themself off their chair so carefully and so quietly so they wouldn’t disturb the zen and the room. It was beautiful and there was concentration and introspection, but it couldn’t happen in a traditional davening. They were only able to daven traditionally from, I think it was from yishtabach. They couldn’t do the regular psukei dizimrah.

And so very often the goals of trying to do some of the most introspective spiritual things comes into conflict with having a traditional minyan and a Halakhic minyan. And those things can be very, very complicated. And a lot of the times those were the things that we were asking ourselves in the school. If you want to spend 10 minutes talking about the avoda of tefillah, you’re going to lose something because of the finite time of a school day. Can we skip half of… There’s a whole bunch of questions there, and every school asks their own posek. Every school has their own mahalakh. Every minyan does a different thing. But those are the questions that these school people are thinking about.

What has to give because, you cannot do everything. You cannot have the perfect Halakhic minyan going at the right pace, at the right time with the right amount of discipline, with the right amount of kids being able to follow and participate and also finding soul and spirituality. The glass is overflowing.

David Bashevkin: 
I personally, and I don’t know if you agree with me on this, I always veer towards the traditional to the routine eyes. I think when people talk about spacing out during davening, I actually think there is a value to learning how to space out and then return back to the moment. And I find it very hard to orchestrate daily spiritual moments. And instead to teach teens how to space out productively or at least to space out without disturbing others. Give them, I don’t know, it’s like a kiddie toy to play with, whatever it is. Read a book, do something rather than pray, which I know a lot of people in the cohort did.

Debbie Stone: 
I’m a huge fan of offering books for kids who say, I can’t pray right now, or I don’t want to pray right now. That’s a big struggle that we have in schools where kids will say to you, you won’t make me talk to God. You can’t make me have a genuine conversation with God. That’s ridiculous. I’ve had kids who say to me, you can’t make me put on Tefillin. And I understand that, I respect that. I do believe it’s important to offer reading material. And I do believe what you said before about finding your way to do what you need to do without disturbing others is a really good lesson. When I was a child in shul, I remember this, you know, think about your early memories, but when I was a child, my parents would bring us to shul and a lot of the other kids were allowed to run around.

They were allowed to run around outside, in the courtyard and the shul building and made a massive noise, but parents bring their kids to shul and you go with it. I always used to look up at whoever I was sitting with, mother or father, and I would look, can I go play? And the answer was no. We don’t run around in shul, that’s not what you’re doing here. You don’t need to doven, here’s a book, enjoy.

I did a lot of reading and I remember someone said this many years later in life, if you do that with kids, they absorb a lot. They absorb a lot. I used to know the tunes and every so often, my mother or my father would point, we’re up to Kedushah now, you can take a pause from your book and participate and then go back to the book. I absorbed the rabbi’s speech. I would absorb the tunes, I would absorb how to doven. And then I’ll go back to my book and automatically at some point I joined in. It’s not everyone’s style.

David Bashevkin: 
I’m thinking back to my own education. Again, not the education I got in the school, but the education I got from my parents. My mother, as I’ve mentioned before, was a very gifted educator to children, particularly around prayer. I always have this moving story, I’ve repeated it many times. I’ll probably have already repeated it in the intro to this very episode, of coming home from first grade saying, mom, I don’t like Ashrei. I hate saying Ashrei. And my mother’s sitting me down and using the language of, let’s become friends with Ashrei. Let’s develop a friendship with this prayer, which has always stuck with me.

My father, God should bless him, not the most gifted educator to young children in prayer. And I felt quite suffocating to stay in shul. I wasn’t yet of the age where even reading a book would’ve occupied me. What I used to do on yamim noraim is I would actually take apart my watch and put it back together, which may have been technically prohibited, but I remember spending the entire day doing that. But I just want to push back gently, and I know you weren’t saying it as a hard and fast rule.

I think I gained a lot from running around with my friends in shul during times of dovening. I think I gained a lot from taking walks in shul, even into high school, way into high school, straight through high school. Instead of davening, where it kind of built a home-like relationship and built my muscles for showing up. That notion that you said that even if a conversation with God at points in your life feels out of reach, to feel tethered to kehilla, that notion of community. I mean the walks that I used to go on with my friend Yoni and Akiva, I think I gained something from them and maybe educators would say, no, I was a terrible doter.

Debbie Stone: 
Yeah, I think that’s perfect. I think that different kids need different things. I’m in a shul now where it’s kid central and they run around and scream and shout and the rabbi enjoys listening to the sound of the kids. Because the voices themselves are prayers. If you want to say that, which is a beautiful idea. For me, I can’t concentrate on a single word and it drives me absolutely crazy. Each to their own. Everyone has a different approach. I guess my parents, in their wisdom of knowing each child, knew that for me that would be good. And your parents, in their wisdom, knew that for you it would not be good.

Either way I think both of us found our home in some way, shape or form. In a shul or not, although for me, most of my life has not been in shul, Tefilla has been much more centralized in a home, and in a space that’s more private. That’s always felt safer for me as it relates to dovening. But I would not say it’s a fast and furious educational rule. It’s just something that was a strong memory as a child that things were just seeping in by being present. And yeah, there were the feelings of, I wish I was out there, and you ask, but you’re pushing it and you’re not going to get what you were asking for. But my parents knew that they could say no and it was okay.

David Bashevkin: 
Yes. And my father eventually we developed a system of which parts I should try to be back for. Especially on the high holidays to make sure that you were still present. I want to shift for a moment and talk a little bit about almost you as a dovener. We worked in the same office during turbulent times in both of our lives, and I remembered, I was talking to a friend very recently, Arieh Wielgus, I could call him out. And I was talking about prayer and he said, you know, should really talk to Debbie Stone. She taught me something new about dovening and I was very moved that, again, Ari Realgas is a wonderful individual and it didn’t like shock… It did shock me a little bit that he pointed in your direction, somebody whose many years and all these fancy yeshivas and learning. Again, we all learned so much from Debbie Stone.

But I was impressed by what he told me and why, and it’s something that I learned a great deal from you as well, which is we were both in the office and working together, and in our own individual lives, which we would sometimes talk about it, things were not moving along all that well in our own individual religious lives. We were both individual religious educators, and our religious lives were like pieced together with band-aids. You had broken engagements, your dating life had moved from London back to America, was not moving quite as sequentially. You had these beautiful nostalgic memories of this rich world of Yiddish Kai that you came from. In London I would always hear stories and the name of Diane Arontroy, who passed away this year. Zecher tzadik livracha. His memory should be a blessing for all of us.

And now you were kind of like in exile in America, didn’t have family around you, yet somehow you still showed up. I don’t know if you continued davening throughout, but I’m curious what gave you the capacity to continue davening through a period where nothing seemed to be going right, year after year. I had years where I stopped showing up. You never, at least it seemed to me, stopped showing up. Can you just tell me a little bit of where you developed that capacity?

Debbie Stone: 
Wow. It’s a special question. It’s a question. I think in the totality of those years, which were turbulent and difficult, and I had a lot of questions. In the totality of those years, yes, I was dovening pretty much daily and sometimes with a Minha, without, but shachris daily, I would say for the most part. There were two or three times… Actually before the US, there were two or three times where I could not. There were two very painful times where I just couldn’t. And I remember even speaking to one of my mentors, one of my rabbihem, and I said to Tim, this is too painful. I can’t do this right now. And the most loving and giving thing he said to me was, so come back when you’re ready. Come back when you’re ready. And that felt like such an invitation that I was almost rushing to get back when I felt capable.

That was one emotional time. Another time actually was when I physically wasn’t able, I was actually quite sick at one point in my life in England, and I physically wasn’t able to open a cinder and read. I couldn’t see the words properly. And there was moments where I wished I could. I couldn’t do it. I wanted to and I couldn’t physically, which was a very powerful thing. And I think that gave me so much strength that over the years, if I could physically say it, I would. Even if emotionally I was very, very angry and very, very mad. And there were some days where I would say, I’m doing it short today because I’m cross. I’m upset. As if I was punishing God. It was my little game. You’ll have something but not very much for me because I’m quite cross with you. And I would say the words like that out loud.

And I remember it took me a long time to realize that that was a Tefilla. That being able to say, Hashem, I’m upset right now and I can’t talk to you in the way that I normally do, but I’m still here. I believe that we start a relationship, but I’m mad and I’m telling you I’m mad about it. It was a very real and perhaps non-English bizarre approach to my relationship with God. And I don’t know where you saw that I showed up because most of my showing up happened privately at home. I really wasn’t a shul goer.

David Bashevkin: 
I would see you tucked away in offices. I did, I did see you.

Debbie Stone: 
Tucked away sometimes. Yeah, I did do that sometimes.

David Bashevkin: 
Tucked away in an office and I’d see the door’s locked.

Debbie Stone: 
Hidden away with a hood on.

David Bashevkin: 
Yeah, nobody would be there then you’d see you standing on the corner on the side.

Debbie Stone: 
Yeah. The truth is shul was always a big issue for me, but I grew up with an understanding of women are more than able and willing to doven at home. That’s fantastic. But I used to get these panic moments, pretty much from Tisha B’Av. That the Yomim Noraim were coming, that the Rosh Hashanah, Yom Kippur days were coming and that I would be at shul.

David Bashevkin: 
What was making you nervous?

Debbie Stone: 
Shul. I always went to shul for Rosh Hashanah, Yom Kippur. It was something that if I didn’t go to shul the entire year, because I could daven at home and I do doven at home. Rosh Hashanah, Yom Kippur is in shul for me, not for everyone, but for me. I went one year, it was particularly difficult, particularly difficult. I felt so incredibly lonely and I have felt forgotten and I felt like everyone had moved on with their lives and I was just left behind and stuck. And I didn’t feel that I could do anything more to help myself. I was trying everything, you know, you have all these very kind-hearted people who give you all this unsolicited advice about how to find a husband. I thought I had done everything, including pouring out my heart and dovening, which was going nowhere.

David Bashevkin: 
And just to understand at this point, you’re in your thirties, is that fair to say? You’re in your early thirties?

Debbie Stone: 
Yeah, that was definitely in the early thirties. Yeah, probably. And Rosh Hashanah was coming up and I was panicking. I was really panicking, because I couldn’t fathom what I was going to do on Rosh Hashanah. Certainly not Yom Kippur. And I went to see Rabbi Yakov Glasser, who was a mentor of ours in NCSY and…

David Bashevkin: 
Still is.

Debbie Stone: 
Still is. He certainly is. And I sat down with him and I said to him, I’ve got a real problem here because I’m going to be in shul this year on Rosh Hashanah and Yom Kippur. And suffice to say, Rosh Hashanah is difficult because I find the Tefilla sometimes difficult. You’re praising and you’re speak… All this stuff. I’m like, you can’t give me just one little thing? I’ve been here year in, year out. I think Rosh Hashanah and Yom Kippur also marks a place of when you are in the same place and you go to the same place, and you see this one’s another year in and now she’s got married and now she’s pregnant and now… Life, you can see year on year, it moves for each person. And you’re still there without your hair covered. And I’m wearing the same dress or feeling the same way, and you’re walking around and everyone’s aging and everyone’s moving and you’re still stuck.

I think that was also very, very hard for me. Particularly because I found a shul I liked. I wasn’t going shul to shul. You mentioned my connection to London. What was so important for me for Rosh Hashanah, Yom Kippur was finding a shul that I felt that connection to the Yeshiva world and the world of the Yeshivish dovening, and I dovened in Aish Kodesh, but I think it was maybe the fifth or sixth year I was going back. I was sitting in the same seat and this girl got married and this girl got married, and I felt like I was the only single person in the entire shul. And that everybody was looking at me, which they were not. And I sat down with Rabbi Glasser and I said, I don’t know what to say when I get there because quite frankly, I’m not sorry, because I’m so angry and I don’t want to apologize for anything because I think it’s hypocritical.

And what do I say when I get to this al cheit and I’m just not sorry about it? And what do I say when we get to this praise and this beautiful Tefilla that I just, I’m not really feeling very grateful or thankful. I just can’t do it. And he said two things which helped tremendously. The first one was he said, if you are entire Tefilla experience is about what you don’t have and your entire being is about you thinking about what people see that you don’t have, that everybody’s looking at you because you’re single and everyone only sees the part of you that you feel is missing. That is who you are. And you’ll only be able to relate to yourself and you’ll be only be able to relate to Hashem like that. If you don’t want people to look at you like that and you don’t want to see yourself like that, stop looking at yourself like that. And look at the different parts of Tefilla where you can focus and recognize the other areas of your life because there’s so much there.

If you don’t want to be the single person and that’s the totality of how everyone sees you, then don’t be that person. Be more, do more. And then your Tefilla has more room to grow and to speak in other areas. Don’t talk about that. You can talk about it a bit, but if the entire Tefilla experience is about this piece, then yeah, it’s going to be very, very difficult. That was one thing that he said. And the other thing he said is, wait, you are going? So I said, yeah, I’ll be there at 7:30 like everybody else, I’ll be that annoying woman at the back who’s in the women’s section where the men are trying to come in and grab their sefer and she’s here on time again. How annoying is she?

Because that’s what I do. Rosh Hashanah, Yom Kippur’s the day that I get up for shul on time. She goes, you’re showing up. That’s the Tefilla, you’re there. Say whatever you want to Hashem, you’re there. Say whatever you want. You showed up. And for me that was incredibly powerful because it invited me to realize that dovening has to be more of a genuine conversation and it can’t just be about my list of needs and my repeated request and it hasn’t come true. And so now we’re still in the same place. It has to move with your life and your life has to move. It can’t be about one thing.

David Bashevkin: 
That is incredibly moving. I mean, the conversations that I’ve had with Rav Yakov Glasser, I’m afraid to even repeat them. You’ve kind of almost inspired me to reach out to him so he could say his pieces because it animated my life too. And that period in our lives which we shared together, he was the rabbi to the broken-hearted. And it’s hard to be friends when we’re each broken-hearted. We used to struggle in that time with one another. Competitiveness, jealousy. Because when you’re so fixated on what you’re missing, it’s such a beautiful thing what he told you, you’re just looking at the other person of what they have. And at least I had that. I’ll take full ownership of that.

Debbie Stone: 
We did that much better when you thank God got married and we moved our professional relationship into the personal world where we spent shabosem together and we enjoyed each other’s company in a different… And that’s what we did. We moved the totality of our world into a different space. And that was amazing for us.

David Bashevkin: 
Thank God you got married. It was during COVID. You had a baby. And in many ways, to an outsider, it would seem that all of your Tefillas have been answered, which is a moving thing. Now, a closer examination, and I know you more deeply than that, it’s never quite that simple and that neat. Do you reflect on your life as, thank you Hashem for answering all of my Tefillas and has this next stage in your life affected the way that you relate to dovening itself?

Debbie Stone: 
Yes. I think that culminated in a moment. Although I think when I’m more reflective of it in a bigger picture, sometimes I say to myself that I had to wait for so long for the things that I was given so that I would find a way to pour every single Tefilla into it to get why it was eventually able to receive. It changed things in a different way in two ways. One was, you’re right. You don’t say everything’s now done. Life is not like that. Hashem will always find you places that you need to ask for. But there was much more space for gratitude and much more space for recognizing goodness and for being appreciative for something that you waited for so desperately for so long that you don’t lose that gratitude anytime soon just because it was granted. That’s one piece.

The second piece was finding someone who davens in a way that I can’t touch, I can’t reach. My husband is a dovener in a very pure fashion. To watch him daven is like to be in an audience with God. It’s just, there’s nothing else there. That’s all that’s happening.

David Bashevkin: 
I had no idea about that, with Meny.

Debbie Stone: 
Meny dovens in a way that is completely different to me. I intellectualize it and I personalize it and I make it all about thinking and feeling. And he davens in the most temimastic way.

David Bashevkin: 
Like a simplicity, a holy simplicity.

Debbie Stone: 
A holy simplicity. It’s a very holy simplicity. But to see it, it’s so genuine and it’s so real and it’s so there. And I find just watching, just being part of watching him doven is sometimes a Tefilla for me in itself. That I’m saying, just take mine with his. Just take mine with his. So that’s one part. And then there were those moments which you were just asking, do you feel like you reached, you got there, you achieved? Yes. There have to be. You have to pause in the moments of life that God gives you these beautiful blessings. A moment under the hapor, which you can picture. Suddenly you’re in a space and you have to appreciate where you are and take a picture of that memory and say, I’m capturing this as a holy memory forever.

And then the surprising ones. So we had our daughter Aravsukus and brought her home and then you lose the moments to daven. There’s a reason why women stop having a chiyuv to daven when they have children. I didn’t really understand it until I had one and realized that the moments to breathe are far and few between and definitely davening. But when those newborns have a bit more time to sleep and they just more peaceful for a few weeks before then they become crying babies. It was first day of Succus and I was alone because my husband went to shul to name the baby. And I wanted to daven. I was just sitting, watching her, and I couldn’t do the whole of Davening, but I wanted to say Hallel. And I said Hallel.

And I remember singing Hallel by myself and this house with this perfect little child sitting there next to me. And it was a moment of the most incredible to fill a joy, to sing praise and feel it so perfectly that something really happened. And you know that’s not going to last forever. You know that that’s not going to be your feelings forever because by nature, life brings you more things. You need to ask for more. You have more needs, you have more fears, you have more worries.

But I don’t think anything can be quite as significant as the period of time that you mentioned when we’re really alone and we were really searching and we felt really left behind. And indeed parts of time when, thank God we didn’t wait for too long, but there were moments when we were waiting for Lily to come along and those feelings of really needing to push in the dovening arena and go back to those places where you talk to God in a very real way. And it’s just really lovely now that I ironically don’t have time to doven at all. And I wish I could.

There are moments in the morning where I say something very fast and I wish there was more, or the precious moments at night where I put Lily to bed and I say Shema with her and there’s never been more Kavanah in a Shema in my life because I’m saying it for two or it’s very different to say vshinamtam livanecha when you are trying to say it with your child, for your child, which is part all encapsulated with so much yearning. Not just when you get married, but from before. I don’t know for you, but for me, part of being single and yearning was also for children. It wasn’t just, I want to find a husband. It was, I want a husband and children. It was all encapsulated in one. So sometimes I feel like I wasted for her for the same amount of time that I waited to get married, which was too many years to say out loud.

David Bashevkin: 
The fact that you have seen and been able to experience that Hallel moment, that each of us in our respective lives went through those periods of isolation and loneliness. Not everybody has the resolution that each of us had in our respective way, and the fact that we merited to have the lives that we have, which is really, it was beyond our wildest dreams because it was our wildest dreams for so long and never happened. So it felt beyond, it felt otherworldly.

And the fact that we are living in that world right now, whenever we get together, it feels [like] seeing the world to come in your own lifetime. It is such a privilege and pleasure to speak with you today, Debbie. And I hope we get a chance to catch up in our more casual tense with Hobo, with Meny, with barbecue and drinks in the old fashioned way.

Debbie Stone: 
Yes, yes.

David Bashevkin: 
But I cannot thank you enough for taking the time to speak with me tonight.

Debbie Stone: 
Thanks, David.

David Bashevkin: 
Debbie mentioned the impact that Rav Yakov Glasser had on her relationship with prayer. And learning how to pray kind of with the totality of your life, with frustration, with anger, with pain, with distance, with closeness, with joy, with gratitude. And I figured Yakov is somebody who has had an impact on me over the last 10 plus years that I’ve known him, perhaps more than anybody else. I call him, and I’ve mentioned him before on the podcast. I call him Yakov, but my interiority, my relationship with him is really one of a rabbi wrapped in friendship.

I always get emotional when I speak with him. He’s also one of the funniest people I know. But this was a very serious conversation. I reached out to him after after speaking with Debbie because he was mentioned so frequently. God willing, we’ll have a longer conversation just with Yakov and his approach to YiddishKite, which is so outstanding. But I wanted to include a brief conversation that I had with really a mentor, a rabbi wrapped in friendship, a brief conversation with Rev Yakov Glasser.

I want to talk about Tefilla with you, and I want to talk about three aspects of Tefilla that I have heard from you. The first is, I know that you have a very unusual custom, which is not related to Tefilla per se, but when someone is going through a time of…

David Bashevkin: 
… related to tefillah per se, but when someone is going through a time of real difficulty, there is an instinctive reaction to check your mezuzahs right away. You want to check the mezuzahs to make sure everything is okay, and you have a very curious way of how you deal with this. I was wondering if you could tell me what you do for people who want to check their mezuzahs during a difficult time and why do you do it that way?

Yaakov Glasser: 
So, often reacts to a challenge in life with something like checking a mezuzah, because they want to attribute whatever’s going on to something concrete that’s within their control, and maybe if I could unroll this little piece of parchment and discover some sort of void or problem or goal in the mezuzah, then I can anchor whatever’s going on in my life to this problem, to this issue, and if I fix this, I’ll fix the problem, and it’s an understandable human reaction. Because the greatest and most profound dimension of going through a real life challenge is the loss of control, is the loss of the ability to kind of navigate yourself back to that sense of stability, and this is something that’s within reach, and the truth is that The Gemara says that mezuzahs provide shemira, they provide protection. It’s not a mystical, not there’s anything wrong with something mystical, but it’s not just a segula or something cultural or whatever.

There is a bonafide notion that these things are on our homes and they provide a level of protection, and the way it’s introduced in the Torah for the very first time when the blood of the sacrifice of Pesach placed on the doorway, that was for a form of protection. So, it’s an understandable approach, but I find that there’s also a danger in this approach and in validating tumah, which is that number one: often people will discover there is no problem with their mezuzah. Now we’re back to square one, except with an additional layer of sort of disappointment and frustration, or they do discover a problem with the mezuzah, and now there is a new issue, which is the guilt that they feel that here if they would’ve checked sooner, if they would’ve checked more, then somehow this would’ve prevented this thing from happening.

So, my approach to this with people is always to tell them, look, at the end of the day, we don’t really know why these things happen to us. We don’t know why God brings some of these challenges to us, but we have it within our capacity to rise to meet these challenges and to allow them to become an opportunity for us to grow and to contribute and to make a difference in the world, and to discover strengths within ourselves that we were previously unaware.

So, if you want to check your mezuzah, because you find this to be a period of time in your life where you feel like a greater affinity to this mitzvah, I want to be a little more careful with the mitzvah that relates to the protection of my home, I’m all for that, and I think you should do it, and I hope you do it, and I’ll find you someone that could do it.

But if you’re checking a mezuzah because you think that a problem in a mezuzah caused cancer or caused death or caused a heart attack, and even if it’s something that’s overtly indicates that in some way, I don’t know, the lamed of livavecha was a problem, and maybe it is true, maybe there is a connection, I don’t know, but the truth is that when you’re facing the challenge in life, you have to really look within yourself, and if the checking of the mezuzah is an expression of that introspection and that growth, it’s a great thing, but if you’re trying to delegate that part of the process, which is a very, very difficult and challenging part of the process, much easier to just collapse, but if you’re trying to delegate that to this particular issue, I personally find that to be not the healthiest.

David Bashevkin: 
You didn’t mention explicitly; so what do you in fact do when they check their mezuzahs?

Yaakov Glasser: 
No. So we’ll check the mezuzahs, and it depends on the person, right? Depends on the person and what their mindset is. So, if I feel like we’re in a good place and they just want to check their mezuzahs, okay, I’ll connect them to someone. Whatever. But sometimes I’ll tell them Okay, give me all the mezuzahs, and I’ll get them checked and then I’ll return them and you have nothing to worry about. Your home will be in full mezuzah compliance with no issue, and you don’t need to, it’s not relevant. Which one was an issue? Which one wasn’t an issue? Was it the bedroom of the person who’s in crisis? You know? Was it somewhere that wasn’t it the home itself? We’ll check the mezuzahs, we’ll fix the mezuzahs if there’s anything to be improved upon, if something needs to be replaced, sometimes that’s fair, you know you have to tell somebody something needs to be replaced, and we’ll get them back up on the home, and this way it becomes a process that’s more about mezuzah and less about trying to be attributing this crisis to this particular thing.

David Bashevkin: 
I’ve always found that incredibly moving, and I think it says something profound theological that you pull people out of that slot machine game of what’s going wrong in my life.

Yaakov Glasser: 
The problem is that when things are going wrong, look, we believe that there’s something false, schar vonesh, there’s reward and punishment in this world, but there is also the notion that God does things that are challenging and painful to righteous people. So, you don’t always know when something’s going wrong, if it’s going wrong because this is a punishment, the Torah describes punishments, or if it’s going wrong because you’re amazing and you’re just the subject of this divine working of the world that is beyond human comprehension. When you sit at the nexus of those two possibilities, you have to act in ways that create meaning and purpose in the situation, not in ways that almost exacerbate that tension, and finding a problem with your mezuzah and not knowing what really that’s about. I don’t know. I don’t find in the emotionality and spiritual growth of the situation for that to be helpful.

David Bashevkin: 
You’ve worked in many different spaces, both as a congregational rabbi, you’ve worked in NCSY. I’m curious, when somebody approaches you, they know how to read Hebrew, they have a siddur, they’re familiar with prayer, but they are struggling with davening. It is either meaningless to them, they feel a sense of distance, they don’t feel a sense of connection. I’m curious, what advice do you usually begin with when you are trying to anchor someone’s relationship with prayer itself?

Yaakov Glasser: 
I think the first thing that I try to help people see is that prayer is not a ritual, it’s a conversation, and it’s a conversation that’s taking place in the context of a relationship, and if you want to understand how to relate to prayer and relate to your prayer, then the first thing you have to look at is the context of your relationship and your relationship with God. You could look at a child who says something to their parents, the expression could be interpreted as tremendously offensive chutzpadik, or it could be actually very loving and kind of just like joking around, and how do you know? It could be the exact same words, the exact same expression. You don’t know. They know. The person watching doesn’t know, but they know, and the reason they know is because they know what the context of this conversation is, and they know what the relationship really is.

And if the relationship is one of hostility and tension, then something like this is aggressive and hurtful. If the relationship is very, very close, then it could be more lighthearted and that kind of thing. So, I really believe that the first thing to look towards in tefillah, in prayer, is what is the nature of your relationship with God? And I think that that has many components to it, but two of the most important components is sort of the foundational connection that sort of underlies your life journey in terms of your faith, and your sense of reality that God is there and he’s present in this world. So, the being that I am coming to pray to is one that I relate to as in existence and real, and then we have to recognize that different points in our life, our relationship with God is different, even though the siddur text stays the same, and that’s true about the family also.

We could have moments where God’s presence in our life is very overt and very felt, and prayer means one thing. We could have other moments where God in our life is very concealed and we’re in a lot of pain and there’s tremendous amount of struggle, and so then that very same conversation means something else, and I think that if you want your prayer to be authentic and you want it to be sincere and you want it to be an experience that’s real, then you need to relate to where you stand in terms of your broader faith context. I think it’s a mistake that people, sometimes, the continuum that they use, is how strong is your faith? How weak? You could ask someone with very strong faith in a very weak moment, and prayer could actually be very helpful. Could ask someone with very strong faith in a very strong moment, and prayer could be very uninspired and it seem almost superfluous and just has to be ritualized to check the box.

I think a person has to be very personal and very real and very authentic of where they are, and I think if you do that, then you could find that prayer has the capacity to serve as this medium of dialogue in very different spots and in very different periods of your life.

This is totally irrelevant, but I was in Rochester for Shabbat and I had to get home on Sunday because my daughter was graduating college. Everyone in the family was very nervous that I had taken this trip because you travel a lot so you know that planes are unpredictable and flights are unpredictable and they get delayed all the time. So, I took a 6:00 AM flight, so it would be the first flight out of the day. So, Saturday night I stood up to daven Shemoneh Esrei, stood up to daven, to pray on Saturday night. And usually each of the blessings have their own little thing that you pray for, and you’ve got your wisdom going in your wisdom, and your repentance going in your repentance, and I want my job to go better and my relationships, you know? And then that piece going better and that’s in that spot, and this is health is in this spot, and no matter what I tried to focus on, all I kept coming back to was please let this plane take off on time.

Let this plane take off on time, and it was like, please give me the wisdom that I could teach the Jewish people Torah, but please make this plane take off on time. That wisdom won’t matter if my wife is so upset. So, eventually I stopped resisting and I just sort of leaned into it and I looked at God and I said I’m going to say these words, because part of our relationship is, there are some things I pray for every day and they’re important to me and they’re important to me, but if this is going to be an authentic conversation right now, I really only care about one thing, and that is I need to get home to my family. Please let this flight take off on time. And it did.

David Bashevkin: 
I want to conclude with something that I wrote down when you told it to me. You, like many people, have been through some very real stuff in life as life is with us, and you had a meeting with a very famed personality who’s no longer with us, with Rav Moshe Shapiro, and he gave you very intriguing advice about what your personal emphasis, what your personal focus should be in this time of difficulty, and I’m wondering, because I had found it so moving at the time, if you could share what he told you at that time, or some of what he told you.

Yaakov Glasser: 
Sure. So, it was very shocking to me. It was very shocking to me. You would think that if you’re in dramatic economic crisis, the point of prayer that you should be focused on is for sustenance, and if you’re in dramatic health crisis, the point of prayer that you receive, the greatest emphasis, is prayers for health, but he guided differently and he said the point of prayer that you should be most focused on is the blessing of modim, which is the blessing of gratitude.

He said the most important thing when you’re in crisis is to not lose sight of everything else that you do have, and going back to the first point that we made about the context of prayer, this was so profound. Because what he is essentially saying is that if there’s a context of gratitude for everything else, and your life and your appreciation for life and your engagement with life is not exclusive to the crisis, then when you’re approaching God, you’re not only approaching the being.

That is the source of what goes on in this world, including this crisis, and you’re sort of negotiating, kind of like we’re having a bad day at the office and this is a problem with the boss, and we’re going at it back and forth, but rather you’re taking a step back and you’re saying, look, there’s a lot going right here. I have an amazing support system. I have, let’s say my own health in this situation. I have a certain capacity to deal with these situations. If it’s a health situation, I have access to extraordinary medical care. If it’s an economic situation, I have access to certain… I live in a country where at the end of the day there are safety nets that could help me. I have friends I could go to. To take a minute and to just thank God for the ability to breathe, and the ability to walk, and the ability to function, and the ability to cry, and all the people that are with you in this journey, and from there to be able to say: and I really need your mercy on this particular space.

It changes the whole dynamic. It changes the whole dynamic then to just simply only approach in the context of that challenge.

That was amazing guidance and I’ve tried very hard. I’ve tried very hard to employ that, not only in the context of prayer, but in other spaces of my life as well. When things are not going the way I really would like them to be going, in any particular area, and that’s where I need support and help. To try to look at what there is to be grateful for, and it’s interesting that it comes towards the end of the Shemoneh Esrei sort of after you’ve asked for everything, and you think you’re going to walk away from this conversation in a mindset of everything you lack, because that’s what this has been, and the whole prayer service from the very first moment builds up to these moments of asking for these things, but really when you ask for these things, it’s also a statement of everything you’re missing.

You’re missing the wisdom you really need and want, you’re missing the sustenance, you’re missing the health or those you love are missing the health, you’re missing redemption, you’re missing justice in the world, you’re missing mental stability. There’s so much you’re missing, and if we just sort of end prayer with that, so then that kind of casts our relationship with God as one that this is the end of the conversation. This is everything I’m missing.

Whereas we take a step back and we’re like, you know what? Let’s not forget all there is to be grateful for, and then the real culmination Tefillah is for peace, which is not just for world peace because when you look at that prayer, it’s not really just about world peace, it’s about a sense of shlemut, a sense of shlemus, a sense of completeness, wholeness. Wholeness means there’s stuff you need and there’s stuff you have. In human terms that is being whole. There’s no such thing in human terms as having everything you need. That is wholeness, and if you can experience the gratitude and experience the wholeness, then your prayer kind of lands in a space that we can talk again in a few hours and see maybe we could get a little further.

David Bashevkin: 
Rav Yaakov I cannot thank you enough obviously for your words today, and even more so for all of the personal words that you’ve shared with me over the years, the personal prayers. I cannot thank you enough for joining and sharing us today.

Yaakov Glasser: 
It’s a pleasure and it’s an honor, and continued incredible success with this amazing medium of impact that has inspired and educated and lifted up thousands and thousands of people.

David Bashevkin: 
You know, a theme throughout, and didn’t really coordinate this, is the importance of Modim. You know, Modim, the prayer that we say for gratitude, when we bow for Modim, the Talmud in Brachot says, you’re supposed to bow very quickly and get up very slowly, and the Maharal in Netiv Ha’avot, I think in the 10th perek has a beautiful explanation for why, and it has to do with how we build ourselves in the context of prayer.

When life sends you a crisis, you fall apart in an instant. You fall apart in a moment, and when we bow, and we have that deference and subservience to the precariousness, to the vulnerability of life, it happens in an instant. When we get up, and we get up specifically with the name of God, it takes place very slowly because our very sense of self really unfolds through time itself. It’s the medium through which we build a sense of self, and very often what we think should happen is we fall apart, and then we want to get ourselves back together in one quick instant and kind of go back to where we once were before everything felt so vulnerable and so out of control and out of our control, and what I believe the Maharal is telling us of why we get up so slowly is the vehicle for constructing yourself is not to turn backwards and try to reclaim that self that you had before life got difficult before life felt that it was out of your control, but it was actually slowly, through time itself, to heal and build a new sense of self. To use time, and specifically through the name of God where we get up slowly, to use that as a vehicle to reconstruct a new self, to reconstruct a new way of living and moving forward, and I think that is what prayer ultimately is all about.

The Baal Shem Tov famously said, the entire parsha of Noah, the story of the flood and going into the Teva, the ark, is really a metaphor for prayer, and the metaphor of course is from the very clever association that Noah’s Ark is called a Teva, and Teva is also the Hebrew word for a letter. When Noah goes into the ark and the wars are raging and he brings his family into the Teva, the Baal Shem Tov looks at this as a metaphor for the way that we should approach prayer itself. We should bring our entire selves, all those we love into the words of prayer, to uplift them and protect us from the precariousness, from the vulnerability, from those raging waters that seem to engulf us in our lives, to find some protection in the moments of prayer itself, and I’ve always been very moved by carrying that analogy through, which the Baal Shem Tov also does explicitly, which is how you bring illumination into the Teva. In Noah’s ark, there are two opinions for how it was illuminated.

One approach is that they had this stone that kind of was self illuminating, that sparkled in a way, and I think there’s an approach to prayer like that. That every teva, every letter, every word of prayer is like a stone and has its own meaning and value and is able to cultivate what our true needs should be, and able to kind of cultivate that sense of vulnerability that we should be experiencing in the world that should be coming naturally to us, doesn’t always, but should be coming naturally to us, and where through the words themselves of prayer, those fixed words of prayer, we’re able to have this self illumination of all of the priorities, values and vulnerabilities that we experience in the world.

But there is another approach to how illumination came into the Teva, the ark of Noah, and that is not through a kind of like light bulb, but actually through a window. And a window is a way to peer out at everything else that is going in the world. It needs kind of its own independent source of light, whether you know it’s sunny outside and it gets filtered in through a window. You’re able to look out at all the other things going on in your life, and in many ways, I look at prayer in the same way that every word, every letter of prayer, is a window for everything else that you are experiencing in your life. To look at your economic life, at your physical life, at your health, at your family, at the satisfaction, at your friends, and to kind of approach all of those existential needs, wants, hopes, aspirations. To contend with your very humanity before the divine.

The act of prayer is a window for you to peer out and everything else that you are experiencing. Bringing yourself and all those you love into the ark of prayer, into the Teva, the letters of prayer itself, serving as a window to peer out and assess on all the things that we try to ignore or hide or turn away from, but the moments of prayer are a moment to look out and really confront everything that we are contending with, and for some people that comes extraordinarily naturally. For some people it is more difficult. Prayer feels like that fundraiser where you’re raising funds for different programs, different buildings, different ideas, but I think the ultimate expression of prayer is, of course, the aneet feela, of finding out how we in our very existence embody the vulnerabilities, the continuous prayer of the neshama, of our souls that are constantly praying throughout our lives, and contending with all of the hopes, aspirations, and vulnerabilities of our lives. To peer out through the window of prayer and find a moment alone with our thoughts before God.

So, thank you so much for listening. Once again, thank you to our sponsors at Mosaica Press. Big shout out to my friend Menachem Tannenbaum. You really want to check out his book. Again, that’s Three Steps Forward, Unlocking the Shemoneh Esrei, our connection with Hashem based on Yonason Eybeschutz, among so many other books, all of which you can check out at mosaicapress.com. Thank you so much for their incredibly generous sponsorship, and their incredibly impressive scholarship and library of books that you want to be sure to check out on prayer and so much more. This episode, like so many of our episodes, was edited by our dearest friend Denah Emerson. Denah, we thank you, we see you, we appreciate you. I know it is not always easy, but you by our side really helps us do everything that we need to do, and you are of course a part of that us.

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