Today, I want to share a chat I had with my son one Thanksgiving. He hit me with a question that caught me totally off guard. See, as a family, we’re doing alright. We’ve got a cozy home, three cars, take trips, dine out—a typical suburban deal.
But back then, we lived in a pretty wealthy town. It’s one of those places with horses everywhere. Bruce Springsteen’s got a pad there. So does Michael Bloomberg. You get the picture—lots of rich and famous folks around.
So, we’ve got quite a few wealthy friends (sadly, not Springsteen). Out of nowhere, my son asked why our friends had bigger houses and flashier cars than us.
He wasn’t being rude, just curious. He knows I’m savvy with money, so he wondered why we didn’t live like some of the folks we know. I told him that the choices his mom and I made contributed to our financial comfort and, more importantly, our happiness.
Growing up, lots of my buddies had money. We didn’t, but I never felt deprived. We were solidly middle class—my dad worked as an assistant principal and mom was a homemaker.
I never tried to keep up with the wealthier crowd, and my friendships were based on real connections, not their parents’ businesses or their houses. Those guys are still some of my closest friends, even after 30 years.
Our house, at the time, was way bigger than the one I grew up in, but smaller than lots of our friends’ homes. We told our son that having a mansion didn’t matter to us. Coming from an apartment, this place felt big enough. Our goal was making a home, not just having more space. Plus, buying that house freed up some cash that we used to invest in rental properties to generate income.
He got that.
Some pals have fancy cars. One even drives a Ferrari. I told him cars weren’t my thing. I just want something safe and comfy. I usually pick up used cars—not beat-up junkers, but well-kept ones. That way, someone else absorbs the hefty depreciation hit.
The money we save on cars goes towards investments and travel.
Every summer, we take a big family trip. The kids love it and I’m sure these are memories that’ll stick with them.
I also pointed out that some folks with massive houses and high-end cars can’t really afford it. We had a neighbor who boasted about his $400,000 a year income when we first met—even though I hadn’t asked. A year later, his business folded, he lost his house, and ended up selling trees from his yard for cash before getting evicted.
Another friend of ours, after a divorce, bought a new Mercedes, even though he had to downsize his home without his wife’s income.
Looking around our place, I mentioned how we don’t clutter it with knickknacks. We prefer spending on something like our big, comfy sofa, which is the heart of our living room. It’s where we gather for movies, board games, and the occasional nap (wish that happened more often).
I explained to my son that some friends with the beautiful houses or fancy cars might never go on vacation or are close to financial trouble.
Those are the choices they’ve made. If they’re happy, then good for them.
For us, the priority is investing in assets that generate income and spending money on experiences like travel.
I’m a pretty chill person. I do my best to keep stress out of my life. Money, or lacking it, is often a stress factor, especially in marriages. Many couples split over it.
Early on, my wife and I decided not to let finances stress us out. During tough times, we’d cut back. We saved for possible rainy days, and supported each other’s hustle.
I pointed out to my son that we never fight about money. That’s partly because we’ve avoided unnecessary financial pressure.
As we wrapped up our talk, I told him some friends have bigger houses and more money, and some don’t. But none of that really matters. What counts is that we’ve made choices allowing us to live how we want.
I asked him, “If we had an extra million in the bank, would you want things to be different?” He thought it over and said, “I don’t think so. I like how things are.”
Mission accomplished.
