Crying for Help

Mattis Gilbert, a Stoliner chassid from Monsey, never planned to get into financial coaching. On a 2008 visit to the kever of Reb Shayale Kerestirer in Hungary, he was inspired by the generous soup kitchen operated by Reb Shayale’s descendants and modern-day chassidim. Upon his return to Monsey, he declared, “I’m going to help people like Reb Shayale did,” and built RSK (named after “Reb Shayale’s Kitchen”), an initiative that distributed freshly cooked meals to families in need.

Then a strange thing happened. The mother of one of those needy families brought the food back to him. “I’m a strong, healthy Yiddishe mamme,” she said. “I can cook for my children. I want to cook for my children. I just don’t have money for the ingredients.” So Mattis pivoted to grocery assistance instead.

But the pivot didn’t end there. Many of his recipients, he realized, were just like that woman. Why not get to the root of the problem, and help them achieve financial solvency instead of relying on constant handouts?

Today RSK has morphed into a sophisticated, professional coaching system that helps thousands of families achieve financial clarity and peace of mind as they overcome financial ignorance, poor spending and saving habits, and debt. “People approach us feeling profoundly lost,” says Chaya Fasten, RSK’s Director of Financial Coaching. “Many just don’t know how money works, and we see how their financial stress affects their shalom bayis, parenting, and health. We’ve even helped a client who was five million dollars in debt. The numbers don’t scare us, because we have a system and a proven process, and it works.”

The RSK process spans six months, with one meeting per month at a very affordable $150 per meeting. They employ 30 coaches, and offer sessions in Brooklyn, Lakewood, Monsey, Monroe, and Montreal, with more locations planned to launch in the coming year.

The Living Smarter Jewish (LSJ) initiative, a project of the Orthodox Union, was formed during Covid with similar intentions: to provide high-quality, free financial coaching to frum families who are struggling to balance their books. “As the word gets out and people hear how effective the coaching is, it’s grown very quickly,” says Ilana Pleeter, who runs the program. “This past year, we coached over one thousand five hundred couples. In 2026 we expect to coach over two thousand.”

During the first year or two of LSJ’s operation, many of the clients were in real crisis. “Debt is a major issue in our community,” Ilana says. “We worked with someone who was building a custom home while they had tens of thousands of dollars of credit card debt.”

At this point, debt is the motivation for 27 percent of LSJ’s clients; the other 73 percent are looking for proactive guidance.

Ari Stern*, a real estate investor who lives in the Tristate area, volunteers for several organizations and also counsels couples privately, free of charge. There is a real need for private financial coaching, he says, and there is also real receptivity in the community. He would know; he sees about 15-20 couples a week.

“A local rav will call me and say, ‘I’m sending you this guy — he’s making a bar mitzvah, he needs this photographer, he needs this caterer, no way does he have enough money for it all, help him figure it out.’ Or I have people calling me from local tzedakah organizations: ‘We’re sending you a couple, tell them they have to stop buying takeout at Glatt Bite and figure out a cheaper way to feed their family.’

“Obviously, I can’t tell people what to do and how to spend. But I can sit with couples and over time, I can help them gain real understanding of how money works in general, and how they can build a budget that works for them.”

The interesting thing, Ari points out, is that he sees couples from all income brackets — even those making six-figure salaries — who are equally desperate and lost. “The best definition that I’ve found of ‘rich’ is someone who makes a lot of money but spends it all. He might bring in a high salary, but he’s still living paycheck to paycheck. That’s different from a truly wealthy person — someone who knows that no matter how much money he makes, part has to go to the future before spending on the here and now.”

Chaya Fasten of RSK breaks down their clients to three basic “types.” Similarly to Ari Stern, she notes that the differentiating factor isn’t income. It boils down to mindset, habits, and behaviors.

The first category is what she calls the “financially stressed” — those clients who encounter regular, significant financial stress, and can barely make it through the month or year. The second is the “financially stretched” — on paper, their income should be sufficient for their expenses, but in real time the pressure to stay in the black is very daunting. The last category is the “financially expanded” clients. Their income is way larger than their needs, but they’re seeking guidance so they can spend more intentionally and plan for a more secure future.

It’s heartening that thousands of couples are seeking professional guidance to manage their money. It’s even more heartening that of those thousands, a comfortable percentage are technically solvent, and even thinking ahead. But it’s depressing to realize that there’s such a crying, universal need for this seemingly basic advice. Why is the frum community so ignorant when it comes to money management? Why are so many families struggling on a daily basis?

A Problem of Basics

The most basic answer might also be the most depressing: Frum life is objectively expensive. Frum couples typically have large families, and they must pay for private tuition, large simchahs, Yom Tov expenses, and summer arrangements. Many struggle with the basics, because in our community the basics are objectively pricey — and they are not optional. By any standard, it’s a truly difficult challenge.

“The first question we hear from so many of our clients,” says Ilana Pleeter of LSJ, “is, ‘how can my neighbor afford all this and I can’t? It just seems so impossible.’ ”

Often, she says, the answer is that the neighbor is likely keeping up the same facade as the client. Frum Jews tend to live in expensive areas, due to their need for religious infrastructure. They send to private schools. They can’t purchase ultracheap food. “Forget about your neighbor,” Ilana tells the clients. “They’re probably struggling, too.”

“In order to survive, a frum family has to be in the top five percent of national income brackets,” Ari Stern puts it bluntly. “People don’t realize that. They don’t plan for it. When I sit down with a young couple, I tell them, ‘this is a war that’s coming, and you have to prepare yourself.’ ”

But even a family that’s making a sufficient income for those basics — a victory in itself — isn’t guaranteed financial stability. There are all too many cultural and social pressures that push the frum family from teetering-but-just-making-it to over-the-edge. So much of a frum family’s expenditures are not technically “basics” — but they still feel like must-haves, due to massive if silent peer pressure. Depending on one’s social circles and affiliation, there are pressures for certain kinds of simchahs, certain brands of clothing, certain calibers of vacations, certain sizes and locations of homes… which most people will explain as “something we just have to do in our circles.”

Ari Stern sees this every week. “People have no idea where their money goes. I think rabbanim have to scream about this. They have to relay it from a hashkafic perspective: If you don’t have a cheshbon how much life costs you, then you’re not doing your basic hishtadlus. Pretty much every struggling couple I meet says the same thing: ‘We’re not making it, but it’s so crazy, because we spend pretty much what we need, nothing beyond the standard.’ And it’s the same mantra whether this couple makes fifty thousand dollars or five million.”

Lack of Education

Compounding the high demands is the fact that many frum adults have never gained a thorough understanding of how money, budgeting, and savings work. It’s no wonder that they’re struggling, with such high stakes and not much practical financial knowledge.

Many frum adults today will admit that money was not something they talked about growing up. “It’s bad manners to talk about money,” they heard. “How dare you ask someone their salary? Why is it your business how much the house cost? Polite people don’t talk about other people’s money (and we don’t talk about our own, either).” And 20 or 30 years ago, there was virtually no formal education about the different types of bank accounts, retirement funds, mortgage rates, or how compound interest works.

“When we meet with newlyweds, we hear about parents who are helping their married children, but still can’t overcome their discomfort talking about money,” Chaya Fasten says. “The newlyweds have received this vague commitment from their parents, but they’re uncomfortable to ask — when will the money be coming in: on the first, the fifteenth, the tenth? We encourage parents who are supporting young couples to be extremely clear about the amount and the terms. Don’t say ‘we’ll give you whatever you need’ — then your couple will always feel beholden, and it will be that much harder to form their own independence in their own marriage. Give them clarity in numbers and in expectations.” It might sound extreme, she says, but many married children would appreciate less support and more clarity.

But even a more open approach to money has its limitations. Today a growing number of schools teach formal financial curriculums, but many students don’t grasp how relevant and urgent the material is. Ari Stern asked a local high school kid about a course in money management his school was giving. “Oh, it fizzled out after two weeks,” he told Ari. “The boys felt it wasn’t really nogeia to their lives.”

Unfortunately, the lack of perceived relevance in high school translates into a dangerous lack of awareness after marriage. Chaya Fasten pinpoints that moment as the perfect time to get help. “Three to six months after the wedding, every new couple should sit down with a coach and receive guidance to get on the right path. At that point it’s relevant, it’s real, but there aren’t any pain points yet.”

Ari Stern agrees. “My ultimate goal is for every single young couple to meet someone like me, two to three months after their wedding,” he says. “I wish I met myself twenty years ago; I could have helped myself. When I meet a young couple, it’s more about basic education — setting up banking, investing, budgeting, life planning. With older people, the process is more complex. The problems are deeper. We do our best to fix things, but it’s usually much harder at that point.”

When struggling couples sit down with a financial coach, they’re ashamed to admit that they just don’t know how much money they have, how much they spend, where it comes from and where it goes. Ari Stern remembers counseling a young couple. They had a decent amount of money coming in every month, but it seemed to magically evaporate, and they had no idea where it was going.

“Well, there is one thing,” they admitted. “We know we spend a lot of money going out to eat. But we’re newlyweds. We’re trying to get to know each other. This is something we can’t give up.”

“No problem,” he said. “Just do something simple for the next month: Every time you get back from a restaurant, write down how much you spent.”

A month later, the couple met him again. “We never realized how much money we spent on going out,” they said. “Not just hundreds. Thousands! It’s insane. We can’t do this anymore. We won’t have any money left if we continue like this. We still want to spend time together, but we’ll start going for coffee instead.”

It sounds like a sweet, naive newlywed tale, but Ari wryly points out that the dynamic isn’t limited to the young and dreamy. “You wouldn’t believe how many people, even people with a lot of money and responsibility, just don’t know where their money is. I meet owners of big companies and show them my system for tracking money, with my Excel spreadsheet. This big boss will say, ‘This is so great, I love it! I’m going to have one of my employees implement this tomorrow!’ And I say, ‘that’s really nice, but you still won’t know where the money is.’”

Grow a Backbone

The most important factor contributing to financial struggles, and likely the hardest one to solve, is a lack of the necessary internal discipline to counter strong social pressures.

We live in a very connected community, with a strong conformist ethos. “Fitting in” matters at every age and stage. Even confident, well-respected people aren’t immune to the pressure to look right, host right, make the right type of simchah, and treat a new kallah or chassan to the right gifts.

Still, it’s unhealthy and unrealistic to keep calibrating one’s sense of “normal” according to one’s social circle. “So many people start the coaching process by begging their coach to tell them what’s normal spending for their family size,” Ilana Pleeter says. “Our coaches will say, ‘who cares what other people are doing? Let’s focus on you! Can you shave a hundred dollars off your grocery bill? Can you challenge yourself to find a creative way to bring in more money? Instead of focusing on what your neighbor is doing, and trying to pin down this elusive idea of “normal,” think about you. What is your budget? What can you afford? How can you change that?’”

A gadol recently spent Shabbos in Ari Stern’s neighborhood, and he rued the way some young kollel couples seem to determine their “normal” according to circumstances very different from their own. “If you’re in kollel, you shouldn’t you have two late-model cars. You have to understand that your lifestyle isn’t going to be like yenem. It’s an understanding that many young kollel couples don’t seem to have.”

The tendency to set one’s personal standards based on the neighbors is doubly dangerous in the frum community, where vastly disparate socioeconomic brackets mix so closely. Secular society often self-segregates based on income; most people vacationing in the Hamptons can afford a certain type of car or clothing. But frum schools, shuls, and summer camps comprise a vast mix of income levels. Unfortunately, too many people emerge with unrealistic expectations: The guy who davens next to me treated the oilem to a $1,000 bottle of liquor at his kiddush, why shouldn’t I? The girl who slept in my bunkhouse has a $200 pair of sneakers, why shouldn’t I? The woman at my weekly shiur just bought a $7,000 sheitel, why shouldn’t I? The boy I study with wears a $140 hoodie, why shouldn’t I?

“The diversity is not what’s unhealthy; it’s that we don’t acknowledge that we’re not the same,” Ari says. “A five-foot-tall person doesn’t think he has to put on stilts before hanging out with someone who’s six feet tall. I’m short, he’s tall, so what. But when there’s a disparity around money, people feel they need to keep up appearances.”

The only way to counter those social pressures, Chaya Fasten says, is to develop a strong backbone. The goal is for every couple in the RSK program to develop what she describes as “a quiet internal battery that drives them toward their financial goals.”

“Ask yourself: Where are we headed, what are we trying to accomplish, what are we hoping to do? Money should be the support to live a beautiful Jewish life instead of a source of tension and contention.”

When a couple honestly evaluates their beliefs, their intentions, their needs, wants, and values, they can set a long-term goal that’s often powerful enough to quash “social norm spending.”

To that end, the coaches at RSK recommend that their clients draft a “family legacy statement” — a sort of mission statement that encapsulates their goals. Maybe the goal is to climb out of debt. Maybe it’s to buy a home or do a large-scale renovation, or something more future-oriented, like dancing at their children’s weddings without debts or financial worries. “We have them write it down, and they keep updating it as their financial situation changes. When people have a clear goal like this, it helps them be very intentional when they encounter social pressures.”

If a couple aims to save $100,000 for their child’s wedding, and they figure out how to translate that into monthly amounts, they are much less likely to cave when yeshivah week approaches and they hear about the neighbors’ vacation plans. They have a clear picture of what they’re aiming for, and they know that an unplanned vacation will knock that picture off-kilter.

That doesn’t mean they won’t be spending yeshivah week enjoying family time, or even traveling where they want to. But the key is that it’s intentional, an inwardly driven decision.

Ilana Pleeter smiles as she remembers a line that the OU’s executive vice president Rabbi Moshe Hauer z”l often repeated: “A bar mitzvah is not a surprise party. You have thirteen years to save up for this.” If you make it a goal to greet your guests at that simchah with true inner joy and menuchas hanefesh — if a debt-free event is an intentional and conscious destination — there’s a much better chance you won’t get diverted on your way there.

What Coaches Can’t Do

Money management is complex and multifaceted, and often, financial dysfunction is entangled with emotional dysfunction. Sometimes a couple will sign up for financial coaching, only to uncover deeply entrenched shalom bayis issues.

“When that happens,” says Rabbi Simon Taylor of LSJ, “our coaches don’t try to be something they’re not. We’re not marital therapists. It’s not what we do.

“That said, good financial coaching can definitely help a troubled relationship,” he says. “It’s so much healthier for a couple to see their finances in one spreadsheet. So often, there’s friction in a marriage because one spouse is shut out of the finances, and the couple isn’t making joint decisions. The process our coaches recommend is much healthier for couples — not just because of the financial journey, but also because of the shalom bayis perspective. With our system, they get used to having conversations about the budget, deciding together where to set priorities, where to spend and where to save…. It’s a much healthier formula for shalom bayis.”

Sometimes a coach will have to struggle internally to stay out of the marriage dynamic. Ilana Pleeter recently spoke to a couple. “The husband is working three jobs and they’re still in debt, but he doesn’t feel it’s his wife’s role to bring in money. I don’t tell people what to do — that would overstep my bounds — but sometimes it’s a challenge, because in this case it seemed clear that something had to change.”

Ari Stern sees a lot of shame and even more blame, as people in devastating financial ruts blame their parents, their childhoods, or their internal scars for their current situation.

“It’s sad, but I see people who blame their parents for everything,” he says. “There’s the famous example of two brothers — one is an alcoholic, the other refuses to touch alcohol. The first brother tells everyone, ‘Of course I’m an alcoholic, what do you expect? My father was a raging alcoholic.’ The second says, ‘I never touch alcohol, and do you want to know why? It’s because my father was a raging alcoholic.’ So yes, you can see everything in your life as someone else’s fault.

“But I’m a numbers guy,” he cautions. “It’s not my job to figure out the psychological underpinnings of your issue. You want to blame whoever you want to blame, okay. But if you’re meeting with me, we are going to talk about one thing: How are we going to make your life better?

“If you’re not ready for that, I can’t help you.”

What They Can Do

If and when a client is ready, though, these coaches have specific and proven tools and systems that can make a real difference.

The first condition is that both husband and wife must be on board. Even if one spouse is completely clueless about the finances, the process cannot start until both are in the same room, ready to work together.

When the couple finds the courage to come in and sit down, they will often find that it’s not as intimidating as they thought. “Our coaches are super nonjudgmental, no matter what the issue is,” says Ilana Pleeter of LSJ. “They won’t tell clients what to do: cut out cleaning help, no more than four outfits per kid. They do point out deficits and offer approaches, but it’s the clients’ life, their priorities, and they have to figure it out. If a client asks ‘where do you think I’m overspending,’ the coach might suggest something. But it’s not our job to tell you how, where, or what to spend.”

“Telling people, ‘Nobody should spend…’ creates negativity,” says Chaya Fasten of RSK. “Nobody wants to be guilted into anything. We want our clients to achieve financial strength and financial peace, and that comes from intentionality. It’s much more productive to help a person learn core principles — to be connected to their numbers. Because that’s the first foundation: Know your numbers, connect to the numbers. Once people do that, they wake up, they’re conscious. So instead of telling them ‘Don’t,’ we start by opening the light.”

The RSK coaches help their clients build a clear map of all the relevant numbers on one shared document. Next, they help the couple isolate a one-year goal and a five-year goal, understanding the family’s needs and income and identifying any gaps, and learning to manage finances proactively and strategically. “This doesn’t fix emotional or relationship issues,” she concedes, “but it brings them together in a very focused and goal-oriented way.”

“The biggest benefit of this coaching process,” one client told her, “is that we can have a direct, open, and healthy conversation about money now. Without the emotional baggage.’

When Ari Stern meets with a new couple, he teaches them the principles of budgeting. “From where I’m sitting, the most important thing is the budget. The difference between successful and unsuccessful people is always the budget. People who don’t budget just get angry and resentful at the end of the month, when the credit card statement comes and they see all these expenses that they didn’t plan.

“People get uncomfortable when I talk about budgeting, but I’m not telling them how to spend. I’m helping them understand how their lifestyle is or isn’t working. When you have only two hundred dollars left in your bucket, where is it going to? If you need help making it, do you know the dollar amount — how much tzedakah do you need?”

People have to understand how all the decisions they made or didn’t make lead them to their future, he says. “When newlyweds take a massive vacation to Rome with chasunah money — they don’t realize it will affect them later, when they want to buy a house or make a simchah. At that point you might be inclined to blame someone else, but really you did it to yourself.”

And then comes the bedrock principle: “Even if you’re not making millions, you need to implement the understanding that for every single paycheck, there’s a certain amount that doesn’t come home with you. After taxes, a part must go to your future. I show them how a couple that starts putting away three hundred dollars every month immediately after marriage will have close to two million by the time they retire. And how a couple that waits two decades or so, until they feel ‘settled,’ can invest six hundred dollars every month — which looks equivalent to the first couple — but will end up with less than half a million. That’s a huge difference.

“Unfortunately, for a lot of people, siphoning off a portion of your earnings every month is a radical idea. But if your kids grow up with that, it won’t be. If your daughter makes a hundred dollars babysitting, teach her that ten dollars goes to maaser, ten to her future. If that’s a child’s basic chinuch, putting away money should not be radical. No matter how small or large your paycheck is, the most important thing is not to spend the full amount.”

Though the coaching process requires focus, stamina, and openness to change, Chaya Fasten of RSK says that it’s fascinating to see how optimistic and empowered their clients emerge. “They feel stronger, more confident, more peaceful. They’ve learned a system that really works. We have families earning a range of incomes — from as low as under a hundred thousand and typically up to five hundred thousand — and they’re using the same foundational principles we’ve taught them to find financial stability.”

Which proves that it’s not about numbers so much as mindset. With the right mindset, even less generous numbers can often work. And with the wrong mindset — or just a general lack of mindfulness — even millions of dollars can be insufficient to support a frum family.

Getting the Kids on Board

It sounds almost idyllic: A couple sits with their warm, encouraging coach for several months, hashing out their budget, setting priorities, making firm financial plans. But then they have to go home and acquaint their children with a new reality. “Kids, from now on, we’re not going to be buying those shoes. Girls, I know everyone is spending three thousand dollars on camp wardrobes, but we’re not able to swing it anymore. Sorry, boys, but you won’t be able to do that road trip with your friends this summer.” How can parents relay their new financial approach to their children? And is this kind of belt-tightening even realistic?

“There’s a very fine line of what’s appropriate to share with children and what is not,” Chaya Fasten says. “Many parents today lack clarity and confidence to determine what to share with their kids. Is it appropriate to tell kids how much our house cost? Will we damage or traumatize them by telling them we can’t afford something? How do we teach kids to manage money when they don’t have much of their own?”

It’s even harder for parents who grew up in homes where money talk was off-limits. But these conversations are important. “And I definitely see the culture changing,” Chaya says. “It’s become okay to speak about finances, to address money issues proactively. People now understand that you don’t have to be in a place of dysfunction to seek guidance in managing finances well.”

That said, the strongest and most impactful message to children is your actual spending habits, not your speeches. If you can’t implement limits, then the prettiest speech won’t accomplish anything.

Ari Stern says it straight: “Parents need the confidence to say no. I don’t agree with the principle of ‘if everyone in the class has it, you have to get it for your kid, too.’ ”

A few years ago, one of his sons asked for a certain pair of sneakers that “everyone” in the class was buying. “How much do they cost?” he asked. A hundred twenty-five dollars, it turned out.

“Not happening,” he said. “I’m not spending that much on sneakers. But I’d love to go shopping with you and I’ll make sure that you get a pair of sneakers you’re happy with.”

There was an unspoken but very clear message there, he explains: “My hashkafah is that I set limits on my spending; there is only so much money I will spend on a pair of shoes. But when it comes to time and our relationship, I have no limits. I want you to feel that you matter to me. That’s an investment I will gladly make.”

Chaya Fasten and the RSK coaches have seen a basic principle play out again and again in people’s spending: When someone’s not managing their finances, but rather their finances are managing them, then whoever yells loudest wins.

“Think of a struggling couple,” she says. “The credit card bill comes in, and since it’s most urgent and obvious, they pay it. But next week, how will they buy milk with an empty bank account? The same is true for social pressures, or children’s social needs. If that’s what is yelling loudest, it will win.

“But I’ve watched families with teenagers facing very high-end social norms, expensive expectations, who went from a ‘whoever yells loudest’ approach to a very intentional approach. They start having healthy conversations with their teens, setting limits without a sense of negativity or burden. It’s very intentional, but the children experience it as a peaceful, noncombative shift. The parents will say something like, ‘Let’s talk about what’s important for you to buy this season, and we’ll aim to get some of it.’ ”

It’s important, she cautions, not to tell children “we can’t afford this,” or “we’re not managing.” The children should instead be hearing “this is what we’re saying yes to, this is where we’re saying not yet, not now, or no.”

In the best-case scenarios, when parents maintain a positive and calm attitude, these conversations can become a source of pride. Children imbibe a value system: This is how our family spends and saves, these are the foundations of our family’s approach to money.

Ari Stern has also found that parents have tremendous power in relaying a healthy (or unhealthy) approach to money. “The main thing parents have to convey is that there is a cheshbon, that money doesn’t just flow on its own. They don’t necessarily have to give their kids a set allowance; the main thing is that they convey a sense of accountability — that money is not unlimited, that we don’t just hand over the credit card to buy and replace without any thought process.”

In short, for a parent to be effective, he or she has to be an adult. An adult understands limits, an adult can forgo immediate pleasure for a bigger goal, and an adult can say no.

Ari enjoys serving as the candy-man in his shul. One Friday, a local father called him and said, “My son is going to come over to you tomorrow for candy. But my wife and I recently decided that we’re going to be keeping him away from anything too sugary; it makes him hyper. So make sure to give him something salty, not sweet. And without any of those artificial dyes, they’re terrible for him. He might ask you for the sweet stuff, but follow what I said. Just make sure he doesn’t know I told you.’”

“So tell me,” Ari asked his friend who couldn’t look his son in the eye and say no. “When are you going to become his father?” —

I can’t believe I spent

$34

on a hair ribbon, but my daughter seemed to need it very desperately. If that’s what it takes for her to make it socially, it’s not a bad price

I can’t believe I spent

$65

per kid per day on “in between” and pre-Pesach camp. It’s not that it’s a standard per se — no one is forcing me to send! Except for the little matter of me having a job that I need to keep, to cover everything else I have to pay for 

I can’t believe some of my students’ parents spend

$1,000

on a winter coat for a high school girl. It’s definitely NOT the standard. But I see enough of them in the classroom to do a double take…

I can’t believe I spent

$375

on my teenage son’s hat, but raising teens demands nuance and balance, and this isn’t a principle I want to stake out here and now with this kid

I can’t believe I spent

$20

on a sourdough challah, but that’s what everyone wants to eat around here. And no, I do not want some of your starter. I know it’s “soooo easy” to make sourdough, but I have way too much on my plate

(Originally featured in Mishpacha, Issue 1092)