Windfall
| April 29, 2025I spent my childhood and young adulthood scrimping and saving. But then, everything changed
As told to Shoshana Gross
Ibabysat the world.
At least, that’s what it felt like.
Evenings through high school consisted of a hasty supper and racing to different houses in the neighborhood. I lived in an area blessed with growing families, and someone always needed a babysitter — and as a brand-loving girl living on a T.J. Maxx clothing budget, I was happy to fill the need — and fill my wallet with hard-earned cash.
It helped that I enjoyed kids.
My two closest friends knew that I babysat a lot, but they didn’t understand why. They were the girls whose living room could fit my entire house, who had an account at the pizza store, who bought another top from Aeropostale (back when it was the trendy brand) just because.
I grew up in a home of because.
We weren’t poverty-stricken, but my parents worked long hours for every dollar, and we rarely spent on anything frivolous. My father never griped about money, and my mother wisely never said that an outfit I wanted was too expensive. They were careful not to burden us with details, but I knew.
“You can choose two outfits,” my mother said when we shopped at lower-end stores.
It was the era of the ubiquitous allowance — and mine was a dollar a week. I remember when snack bags became a thing. I mentioned to my mother that I’d seen one of my friends eating a bag of barbecue tortilla chips. When she surprised me with a snack bag of my own, I was so touched. It was a simple childhood, but I never resented my parents. On the contrary, I respected their basic lifestyle, strong values, and deep commitment to their children — even though I didn’t quite fit the family mold of simplicity.
Seventh grade was the real turning point, when I realized how simple my home was. Suddenly, I noticed brands, developed a taste for high-end designers, and discovered a talent for pulling together elegant outfits.
Abercrombie tops. Coach wristlets. Express skirts. Limited sweaters. They were the height of fashion when I was a teen.
My best friends wore them with a casual nonchalance that I couldn’t help envying. But I would never hurt my parents by asking for clothing they couldn’t buy, so I became the neighborhood babysitter. And even though my friends were always somewhat clueless about my financial reality, their closets were my closets. I would browse their racks of stunning, high-end outfits to satisfy my high-end tastes. As the years passed, I shopped in their closets for school shabbatons, for graduation parties, and eventually, for dating outfits.
College arrived at the same time as my engagement, as well as a lovingly donated outfit to wear to my l’chayim and subsequent Shabbos sheva brachos.
It was my last taste of luxury for a few years.
My parents couldn’t provide much in the way of support — although they did agree to help pay for my college fees. My husband was also in school, but his parents were genuinely poor. Two weeks before the wedding, he confided that he’d lost the part-time job that paid for his tuition — but he didn’t want me to tell my parents, ashamed of his inability to provide.
Nobody knew on the night of my wedding that I was a kallah with little to my name besides a radiant smile, an upcoming college semester, and my husband’s tiny rental apartment. For three years we struggled to balance crushing credit card debt to the tune of $30,000, two babies in quick succession (the second born ten days before my next semester in college), and my husband’s job hunt. He finally found something eight months after the chasunah, but I still had to teach in the morning, work at an office job in the afternoon, take night classes, and tutor between classes — all while taking care of my babies. Supper was the cheapest food we could throw on the table — cheese toast or toast with butter, prepared by whoever came home first, my husband or I — and I would sometimes casually ask my parents for pantry staples. My second baby needed a special formula, and at $38 per can, it literally ate up our monthly budget.
Three years after we got married, my first purchase for myself was a ten-dollar polo shirt at Old Navy — but I was sick with guilt. It could have gone toward much-needed groceries.
And it was painful to dress my babies in Target stretchies when I longed for soft pastels and adorable knits. In the great scheme of things, baby outfits aren’t life-or-death necessities, but clothes had always mattered to me, and this hurt.
Slowly, our situation began to change.
My husband graduated and went to work. It was easier to pay for rent and utilities. Our debt began to shrink.
And then Hashem sent an opportunity and a partner that led my husband in a completely new direction. Almost overnight, my husband’s business took off, and utterly shocking sums poured into our bank account. When that first deluge of money came, it felt limitless. I was the proverbial kid in a candy store, like a starving man deprived of food for years, suddenly faced with a banquet of delicacies.
If I wanted a designer dress, I could buy it. If I wanted those new Louboutin boots, they were mine with a wave of my new credit card.
For my husband, it was an opportunity to spend — on others. The quintessential knight in shining armor problem-solver, he was thrilled to come to the rescue of anyone and everyone. Every tzedakah organization that heard about his recent windfall. The woman next door who was having a hard time paying for utilities. A boy who needed a complex medical procedure in Los Angeles.
Between his softhearted approach to every cause and my adrenaline high at all the latest fashion, we were spending money like it was going out of style — and we quickly realized we needed to rein ourselves in. We set up automatic payments and learned how to budget so we could invest in the business and have enough cash on hand.
It’s a simple pleasure, not having to obsess over the price of basic groceries. And there are benefits I had once barely let myself dream about, like renovating our home with a top designer. Full-time help has also made life significantly easier. She cleans the house, does the laundry, polishes the silver, and babysits my youngest children when I need to go out.
The best part is that she preps my ingredients. My fridge is lined with glass containers of vegetables and fruits. Especially after a baby or when life gets hectic, precut vegetables make eating healthy so much easier. Gone is the toast for supper, 2 a.m. bedtimes after folding endless mounds of laundry, and the exhaustion of working from dawn until midnight.
I am available for my family, and I relish the time I spend with my children.
“She breads the schnitzel so I can take you to the park,” I tell my children. And I do.
But even though I’m so grateful for the ability to live without the chokehold of poverty, there are drawbacks.
My husband has difficulty saying no, and his “friends,” some more friendly than others, seem to think we have a limitless amount of cash on hand.
“I need some help with camp tuition for my son,” someone asked him recently. A lot of our money is sometimes tied up in the business or various investments, so my husband didn’t have much. His $500 donation elicited a, “Can you give me $1,000?”
“If they’re not embarrassed to ask, don’t be embarrassed to say no!” I sometimes tell my husband when he feels guilty for not always being able to give more.
There are so many needs in the world, and I know that firsthand. But as much as we want to help, sometimes we feel more like glorified ATMs than human beings. Almost every conversation turns into a conversation about money.
“Can you help my son find a job/give my son a job?”
“There’s a very worthy cause you may not know about…”
“I really need…”
It’s sometimes hard to know who wants friendship, and who just wants something.
A casual acquaintance invited me out for coffee — to tell me about her husband’s medical issue and ask me to pay for a $20,000 treatment she was hoping I could fund. I did, and I’m glad I could help. But sometimes it’s a random phone call.
“I heard you give people money — can you pay my son’s tuition?”
It’s disconcerting, and I’m still not used to that feeling.
But in so many ways, money has been a blessing.
I have time to volunteer at my kids’ schools, fundraise for local causes, and with the memory of how my friends helped me when I was a teen, I’ve turned my extensive wardrobe into an open closet for friends, family, and casual acquaintances. With a closet now organized by a professional organizer (according to color and season), I do what I love best and style people from my closet. Anytime someone has an event or a simchah, I am happy to dress them from head to toe. I’ll also loan them a Chanel or Dior clutch to go with the outfit, and even lend them coordinating jewelry.
Clothing is my weak spot, and with five daughters, I know how much I can spend on beautiful new outfits every season. But I want to turn the gashmiyus into ruchniyus, so besides for my closet mini-boutique, I give my girls’ outgrown clothes to families who are delighted to receive gorgeous outfits for free.
But it wasn’t enough. Remembering my own struggles, I wanted to give more, so a few years ago, I helped found a hachnasas kallah organization, l’ilui nishmas someone I was very close with, to help kallahs from homes where money can be a struggle. I was there, and I know exactly how they feel. But every kallah should feel like a princess, without financial worries weighing her down as she begins her new life. We provide kallahs with gorgeous gowns and special vouchers that enable them to buy beautiful, top-quality clothing and linens at participating local stores. Each kallah also receives a beautiful free sheitel from one of the best sheitelmachers we know, as well as professional makeup and hair services on the day of her chasunah. And every time we see the joy in a new kallah’s eyes, I know we’re passing on the chesed that so many people did for me.
Money. I know the pleasures and pitfalls of both sides of the coin. Wealth is where Hashem has put us for now, so we try to use it well — and recognize the truest riches. Ff
Please understand that…
Wealth ebbs and flows. It’s not always available to shower everyone with largesse.
It hurts to be judged when…
We have a finite amount of money and an endless number of causes to support.
I wish…
We could feel the appreciation. I don’t even need a thank-you. But just know that we give so much to so many, so please don’t make me feel like I’m not doing enough or pressure me to give more. We follow the halachos of tzedakah — family first, then our community, and so forth. I’m sorry I’m not giving a grander donation to your kollel, but we have people very close to us who need our help first.
(Originally featured in Family First, Issue 941)
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