Dayenu: When Is Enough Actually Enough?
By Jack Strulowitz
A few months ago, I was meeting with a new client. Successful, sharp, knows what he’s doing. We were discussing his personal and financial goals and within the first few minutes he said: “I really want to get to ten million.” I asked him why ten. He said that at $10 million, he wouldn’t just be comfortable with the necessities. He wouldn’t have to stress about the luxuries either. The vacations, the cars, the lifestyle. No more thinking twice about anything. And honestly? It sounded reasonable.
But here’s the problem. Necessities have a limit. Tuition costs what it costs. Your mortgage is your mortgage. At a certain point, those boxes are checked. The luxuries don’t work that way. There’s no ceiling. For one person, $10 million eliminates the stress around luxuries. For another, only $20 million would accomplish that goal. We get the nice car, now we want the nicer house. We get the house, now we want the boat. We get the boat, now we want the plane. This is called “lifestyle creep,” when discretionary spending increases alongside rising income, causing luxuries to become necessities and hindering wealth accumulation. You get the plane and you still don’t have a professional sports team. You still don’t have political influence. Your company is big, but it hasn’t gone public. It never stops.
In Morgan Housel’s The Psychology of Money, he writes that the hardest financial skill is getting the goalpost to stop moving. As someone who works intimately with millionaires and their money, I can tell you that he’s right. And it’s not just about money. Being elected the President of France sounds impressive, but who cares when you’re not the President of the United States? There’s always something bigger.
Now, wanting more isn’t inherently a bad thing. It’s one of the things that drives people to build businesses and chase promotions. But nobody should be deceived thinking that feeling will go away once they hit some number in their bank account, and therein lies the problem.
So, what’s actually driving this? In the Five Towns and in most Jewish communities, we all drive by big homes and expensive cars, and for many, the natural human reaction is to want what they have. But think about what’s really happening in that moment. We see one piece of another person’s life and we build an entire story around it. Nice car means he’s making money. Making money means less stress at home. Less stress means a happier family. Happier family means a good life. This happens subconsciously and it’s completely normal. But it leads us to believe that if we can just get that car too, if we can just make a little more money, we’ll get to that happier life, which is ultimately what we really want.
But how much do we know about the guy with that car? A few years ago, Rabbi Joey Haber discussed this phenomenon on the Kosher Money Podcast, where he listed 15 things we don’t actually know about a person just because they have a nice house or a nice car. We don’t know about their relationship with their spouse. We don’t know about their emotional wellbeing. We don’t know about their physical health. We don’t know about their relationship with their kids. We don’t even know if they have kids. We don’t know their income. We don’t know their debt. All we really know is that at one point, when they bought that car, they probably had the money to do so. That’s it.
The problem is that we’re mistaking a deeply personal need for a financial one. And when we don’t have clarity on what we actually want, we end up looking for it in all the wrong places.
When I sit down with a client for the first time, we don’t start with portfolios or returns. We start by talking about what’s important about money to them. What they value. What their goals are. And most importantly, we distinguish between goals money can achieve and goals it can’t.
Pirkei Avos asks: Who is rich? He who is happy with his portion. At every Pesach Seder for over a thousand years, we’ve sung Dayenu. If Hashem had taken us out of Mitzrayim but not split the sea, it would have been enough. But are we really living this way? If we can’t muster up enough appreciation for what we have today, achieving the life we dream about in the future will leave us in the same place. Wanting more. n
Jack Strulowitz is a Financial Advisor at Bernath & Rosenberg in Cedarhurst, NY, where he helps high–net worth individuals and families manage their investments and build comprehensive strategies for retirement, tax, and estate planning. For questions or to schedule a consultation, please contact [email protected] or 847-962-3352.
The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.
Securities and advisory services offered through LPL Financial, a registered investment advisor, member FINRA/SIPC.


