As January rolls in, the much-anticipated “Yeshiva Break” is upon us. Jewish schools across the tri-state area and beyond close their doors for about ten days, giving families a chance to vacation. But what should be a peaceful time has, for many, become a source of financial strain, social pressure, and even anxiety. While vacations are great for bonding, the reality is that the culture around yeshiva break often creates unnecessary pressures. Whether it’s the cost of extravagant trips or the unspoken competition to “keep up with the Kohens,” many families are left feeling anything but invigorated.
I’ve worked with many families who are struggling. Some are behind on their mortgage, many are juggling credit card debt, and others can barely afford tuition. Yet, they still feel pressured to spend thousands on winter vacations. Why? It often stems from the fear of being the only family who “didn’t go anywhere.” Parents don’t want their children to feel left out when classmates compare trips to Florida, the Bahamas, Israel, or the like. Paradoxically, while families try to create happy memories, the financial stress can cause tension and often overshadow the trip.
Going into debt for a vacation is never a wise decision. A break should refresh you, not leave you worrying about how to pay your credit card bills. Before planning a trip, ask yourself: Can I afford this without sacrificing financial stability? If not, it’s time to explore alternatives. And the pressure isn’t limited to parents. Children also feel the weight of this competition. A friend recently told me his child’s teacher went around the classroom asking where each student was going for break. Imagine how the child who’s staying home feels?!
This kind of messaging reinforces a damaging narrative: that your family’s value is tied to vacation plans. It’s critical to push back against this. Teach your children that their worth isn’t based on where they go, but on the quality of their character and the meaningful experiences they create at home or elsewhere.
If you’re feeling the pressure of yeshiva break, here are practical ideas to make the time meaningful without financial strain:
Stay Local: Explore parks, museums, or winter activities nearby. Day trips can be just as memorable as traveling far. Turn your home into a vacation spot with extravagant themed movie nights, baking projects, family games (for prizes), or indoor camping adventures.
Limit Social Media Use: Seeing others post pictures of lavish trips creates unnecessary FOMO (fear of missing out). Limit their social media surfing and focus on your own family’s activities. If you are fortunate enough to get away, don’t let your kids post where they are or what they are doing.
Get Kids Involved: Let children help plan the break. Give them a budget and help them craft a reasonable “vacation.” They’ll feel more invested and excited when they are more involved in the process. Give them personal incentives to stay under budget.
Defer Your Vacation: Use the break to volunteer as a family. Helping others fosters gratitude and a sense of purpose. As an enticement, offer them a family trip at a different time, which will be much more affordable. Knowing that they are going away a few weeks later will give them the self-confidence to say, “We did chesed now, but we are going to such-and-such place in February.”
Schools must also help by rethinking the structure of yeshiva break. Shorter vacations or staggered schedules could ease pressure on families. Educators should also avoid discussing travel plans in a way that creates unnecessary comparisons among students. The purpose of yeshiva break should be to reconnect as a family and recharge. That doesn’t require a lavish getaway. True happiness comes from shared moments, no matter where you are. By reframing the conversation and prioritizing what really matters, we can reclaim yeshiva break as a time of rest, connection, and contentment.
Would you rather have your kids take one two-week winter vacation or give them two days off each school month? Please email or message me to let me know your choice! Let me know if you have a good “Would you rather” question, and we will highlight your submission.
Shmuel Shayowitz (NMLS#19871) is a respected Real Estate & Finance Executive, Writer, Speaker, Coach, and Advisor. As the President and Chief Lending Officer of Approved Funding, a leading national mortgage banker and direct lender, Shmuel has facilitated over $3 billion of mortgages over the past two decades. Shmuel’s expertise spans various licenses and certifications, including specialized mortgage underwriter, licensed real estate agent, and accredited coach. His market insights and experience are highly sought after in the real estate, finance, and coaching industries. In addition, Shmuel is a seasoned real estate investor and property manager, facilitating thousands of rentals nationwide. Shmuel can be reached at www.approvedfunding.com/shmuel.
