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My wife and I are just getting by and can’t understand why. We are both professionals and bring in about $400,000 a year in household income. We send our six kids to yeshiva, own our home (with a mortgage), save a modest amount of money for retirement, and only go to Miami once a year (where we stay at my in-law’s apartment). Beyond that we quite literally don’t have any more wiggle room. What are we doing wrong? – Anonymous, Long Island, NY

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This question may seem absurd to folks outside New York and Los Angeles. Afterall, an annual household income of $400,000 puts you in the top 5% of the country. However, high cost of living areas can make even relatively high earners feel like they are struggling. This challenge is amplified for frum families, who have the added expenses associated with an Orthodox lifestyle. Allow me to address your question by offering some perspective combined with several suggestions to consider.

Perspective: The lifestyle you are describing is not “just getting by.” You are living a relatively luxurious lifestyle compared to most people and can afford way more than just the basics. First, and most importantly, you are likely spending well into the six figures to give your kids a yeshiva education (priceless). You live in one of the highest cost-of-living areas in the world, with all the kosher/Jewish amenities easily and readily accessible, and don’t seem to be stressed about putting food on the table. You vacation in a tropical climate destination once a year and save money for your future. While you would like more discretionary cash flow, you’re describing a lifestyle that is enviable to many. In short, you are living the dream.

Now that we established that you are in fact living comfortably, the crux of your question is really how to free up your cash flow so that you don’t feel that you are struggling to get by. Here are a few suggestions that may help alleviate these feelings:

Review every monthly expense: This is a super boring suggestion that may get many readers to roll their eyes, but doing an audit of all your expenses is the first and most important step to giving you some financial breathing room. Find the expenses that you can cut or look for areas where you can be more intentional about where you spend your money. The memberships you don’t use, the conveniences that are too frequent or costly, should be cut or minimized. Saving a few hundred dollars a month will lead to thousands of dollars a year, which can either be saved, or used to do something that will spark joy in your life and relieve your financial tension. Small changes to a monthly budget can have a significant impact.

Cheaper schools: You mentioned that you have six kids in yeshiva, which is undoubtedly a hefty annual expense. Thankfully, you live in Long Island, which means you have many yeshiva options available to you. I don’t know where your children currently go to school or how much you are paying in tuition, but with some yeshiva high schools costing upwards of $30,000 a year, it doesn’t take brilliant financial wizardry to realize that you can save a lot of money by sending your kids to a cheaper school. Keep in mind, you can even explore “traveling” to other parts of the state to find cheaper options. While commuting an additional 45 minutes is unpleasant for your kids, and an occasional inconvenience to you, it can save you tens of thousands of dollars a year that you can redirect to other areas of your life.

Switching yeshivas is a significant life decision. It will be disruptive, and another school may have a different style, hashkafa, or other attributes that don’t make it your first choice. However, tough choices need to be made to address your predicament.

Part-time work: An additional $5,000-$10,000 annually may be all the difference you need to not feel pinched financially. This additional income can be earned by working overtime, doing something tangentially related to your field, or swallowing your pride and doing something in the evening or on the weekend that you are overqualified for, but can give you the extra cash flow that you need.

A physician I work with recently told me that he started doing expert witness work to earn an additional $50,000-$100,000 a year so they can buy an apartment in Israel before he retires. Similarly, a business owner, who has a relatively high household income, decided to drive an Uber during his down time to justify taking his family away for Pesach this year (that’s a lot of Uber rides). There is no shortage of opportunities available to those who are motivated and willing to work.

Planning for the future: As the kids move off your payroll and (hopefully) become financially independent, you can direct half of that additional savings towards your financial future and the other half to spend on discretionary items to enhance your life. This approach involves sticking it out in your current situation for at least a few more years. However, understanding that you have more financial breathing room on the horizon, may be psychologically helpful.

Final thought: Remember, your harshest critic is usually yourself. You may feel like you are running on a treadmill and not making any progress, but if no one else tells you this, allow me to be the first: You are doing a good job! While I don’t know you personally or professionally, your question indicates that you are getting the big picture decisions correct. You appear to be serious about educating your children with Torah values that will allow them to be valuable members of a Jewish community and society at large. You also make an effort to take time off as a family, while also saving regularly for your future.

I imagine that many readers have similar feelings of being overwhelmed from time to time. This may be due to financial concerns, perhaps it’s related to family or community obligations. It’s probably all three. Whenever I am feeling overwhelmed, question myself, or feel like I am just going through the motions, I find it helpful to pause and make sure that I am getting the big life and financial decisions correct. While there is always room for self-improvement, the ability to get the big things right in life is what ultimately matters. It will lead to success personally, professionally, and with your finances.


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Jonathan I. Shenkman, AIF® is the President and Chief Investment Officer of ParkBridge Wealth Management. In this role he acts in a fiduciary capacity to help his clients achieve their financial goals. He publishes regularly in financial periodicals such as Barron’s, CNBC, Forbes, Kiplinger, and The Wall Street Journal. He also hosts numerous webinars on various wealth management topics. Jonathan lives in West Hempstead with his family. You can follow Jonathan on Twitter/YouTube/Instagram @JonathanOnMoney.