It’s the beginning of August 2023. The kids are finally settled into their summer schedule, the summer wardrobe is complete, and the credit card bill hasn’t arrived—yet. I take a deep breath, coffee in hand, and settle in with the weekly circular. Finally, a quiet moment.
But then—what? They’re already advertising the winter lines? The autumn/winter (AW) drops are beginning? I feel the familiar wave of anxiety rising. With four children close in age, I need to shop early to ensure I can find matching outfits in all the right sizes. Time to ask Chaim which credit card I can use, though I already know what’s coming. He’ll get stressed, we’ll argue, doors will slam.
But what am I supposed to do? Not dress my kids? Let them show up mismatched, looking like a walking clearance rack, especially when we get together with extended family on Chol Hamoed? It’s not just about the clothes—it’s the feeling of being put together, of celebrating Yomtov with dignity.
Then there’s the food. I love going all out for Yomtov, and Sukkos is my favorite. Throughout the year, I clip recipes from magazines, dreaming of festive meals and beautifully set tables. Who should we invite? I should check the calendar for Chol Hamoed dates—maybe we can plan a nice family outing. I want to invite my cousin Chaya’la; she just moved to the area. It would be so special to spend time together. I also need to check out the new Yomtov disposables—they always release the prettiest designs this time of year. And forget about buying something for myself. Oh well.
That was 2023.
Now it’s August 2025. The kids are settled again. Camp is fully paid, and—miracle of miracles—there are no looming credit card bills. I sit with my coffee and the circular, just like two years ago, but this time with peace of mind.
Yes, the winter lines are out again, but I’m ready. Chaim and I have already discussed our Yomtov plans during our monthly budget meeting. I know exactly what I can spend on winter clothing and Yomtov prep. We’ve been putting away money each month into a clothing account, and some money into a Yomtov account. It’s not everything I might want, but it’s more than enough for what we need. And I think I’ll even get something new for myself, too.
These past two years weren’t easy. Building better habits, committing to financial planning, and learning to communicate differently took real work. But as Tishrei approaches, I can feel the difference in my bones. No panic. No drama. Just peace, clarity, and joy.
How did this family achieve such a transformation in just two years?
Managing Seasonal and Yom Tov Expenses – Joyfully
Many people say: “I want to take control of my finances—but how can I possibly manage the big seasonal expenses?” The truth is, the secret lies in planning ahead. And there’s no better time to start than during Yom Tov.
At first glance, that may sound counterintuitive—why start when expenses are at their highest? But that’s exactly the point. Yom Tov provides an opportunity to see what the real numbers are and to use it as a springboard of growth.
Yom Tov brings with it unique financial realities:
- Reduced income – Hourly workers may earn less due to time off, and payroll can be delayed if payday falls on Yom Tov.
- Extra meals at home – With schools closed and married children or bochurim visiting, the food budget climbs quickly.
- Festive costs – Yom Tov meals, family trips, and outings almost always run higher than expected if not carefully prepared for.
- Seasonal needs – כפרות, lulav and esrog, seforim, clothing, shoes, sukkah repairs, and Yom Tov gifts add to the bill.
- Travel – Visiting Rabbeim, Roshei Yeshiva, or family often means tickets, taxis, and lodging.
- Chol Hamoed spending – The “vacation mode” mindset can loosen financial discipline, leading to relaxed budgeting, impulse buys, higher prices, and “keeping up” with what others are doing.
Yom Tov months are some of the most financially demanding times of the year. Food, clothing, household supplies, travel, and gifts—everything adds up quickly. Yet, that very pressure creates the perfect opportunity to build stronger financial habits.
By identifying these extra expenses ahead of time, planning for them, and tracking how you spend, you’ll not only get through Yom Tov—you’ll gain the tools to thrive all year long. Since the season naturally brings a wide range of expenses in a short period, it gives you a full financial picture faster than any other time. The awareness you build now can set the tone for the rest of the year.
After all, if you can learn to manage Yom Tov, you can learn to manage every other area of your finances. Or, as one wise “hard-squeezed grape” reminds us: “When you’re under pressure, that’s when the real opportunity comes out.”
The First Step towards Financial Clarity is – Clarity
The first step you can take is to simply track every expense. No expense is too small. Use a simple pen and paper or an app to simply observe. No judgement, no overwhelm, simply be curious and open. Do this every day so that you don’t lose track and end with a pile of receipts and question marks.Next, at the end of the season, sort all your numbers by categories: food, clothing, trips, gifts, house, transportation, and any other categories you observe. Look for any patterns that emerge: frequency of purchases, categories of purchases, needs and/or wants, or anything else that you become aware of.
Then write down the total expenses. This then becomes your target budget for next year’s season. Now it’s time to plan ahead. How will you work towards having the money sitting in an account, ready to be spent when the next year’s season comes around?
The Second Step towards Financial Stability is – Planning
There are multiple ways for how a family plans ahead. The goal is not 100% success in the first attempt. Growth happens in increments and financial stability can be achieved slowly and steadily. So the first time you try this, you might succeed in planning for 50% or any number of your total seasonal budget. Celebrate the win and the serenity that comes with spending money that was planned for, allocated, and ready. Then keep growing.Here are a few ways that families plan ahead:
- Some families take the total and divide it in 3,6,9, or 12 months and designate a specific bank account for Seasonal Expenses, into which they make smaller monthly contributions so that the money will be there to spend when the season preparation starts.
- Some families use extra bonuses, gift money, tax returns, or other surplus income to fund this account.
- Some families take on extra work for a few short months before the large season.
- Some families will pause extra spending or saving contributions for those months in order to spend money that they have on the seasonal expenses.
- Some families do a little bit of all of the above.
And so here I am again—coffee in hand, circular open on the table, kids settled into their routines. The ads, the clothing lines, the endless list of expenses—they’re still here, but they no longer carry the same weight. What once triggered panic and arguments now sparks calm conversations and confident choices.
The difference? Two years of small, consistent steps. I started by tracking every expense, no matter how small. At the end of the season, I sorted it all into categories and faced the total—our real Yom Tov number. From there, we built a budget, set up a Yom Tov account, and saved bit by bit. Some months we hit the goal, some months we didn’t, but we always kept going.
Slowly, the chaos became clarity. The same moment that once felt overwhelming now feels empowering. Today, I can shop for Yom Tov with dignity and calm, knowing the money is there, ready for its purpose. Because when you turn Yom Tov pressures into opportunities for growth, the reward isn’t just a calmer season—it’s a life of greater peace of mind, joy, and dignity all year long.
Want help planning your seasonal or Yom Tov expenses? Signup at rsk.org/sign-up or 845-414-8001