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Between Tables is where I explore the emotional, psychological, and practical sides of money, especially for women carrying a lot.
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One of my longest clients asks me some version of the same question every six to twelve months. It’s become a kind of ritual between us. The headlines change. The strategy du jour changes. But the question underneath is always the same.
What are wealthy people doing with their money that I should know about?
I love this question. Not because it has a clean answer, but because of what’s inside it.
It arrives differently depending on the season. Sometimes it follows a headline about the latest hot money moves. Sometimes it’s a FinFluencer who’s found their way across a feed with breathless authority about the strategy the ultra-wealthy use to pass down generational wealth tax-free. But sometimes it’s quieter than that. It’s what am I missing? It’s I’ve checked these boxes, what else is there? An itch to scratch. A restlessness. And honestly, a little bit of it can’t be this boring.
I get it. The 401(k) contributions, the estate documents, the auto-transfers don’t make for a great dinner party story. And there’s something genuinely compelling about the idea that there’s a whole other level of strategy out there, just out of view, that could change the picture entirely.
There’s always a flip side to that coin, though. Win big, lose big. My job isn’t to hold anyone back from taking risk. It’s to help hold them steady while they’re in it, and to be a real sounding board along the way. Not the voice that says no, but the voice that asks: have you thought about what this looks like if it goes the other direction?
When we ask what the 1% are doing, the question is rarely about the strategy. It’s about the feeling underneath the strategy.
First, Who Are We Actually Talking About?
When we say “the 1%,” most of us picture someone on a yacht. Or a magazine cover. Or both.
The actual threshold is more nuanced than the image. In the U.S., the top 1% of earners make roughly $650,000 or more in annual income. The top 1% by net worth starts around $11 to $12 million. In other parts of the world, a net worth of $1 million with get you into the 1%. Which wealthy are we talking about? That question matters before any of the strategy does.
What They’re Actually Doing
The wealthy build generational wealth through vehicles like 529 plans and Roth IRAs opened in their children’s names. The 529 isn’t exotic. It’s a tax-advantaged account that grows over time and can be funded early and often, sometimes before a grandchild even exists. The Roth IRA for a child works if they have earned income, and the wealthy fund it young because they understand what tax-free compounding looks like over forty years. These aren’t tools reserved for the ultra-wealthy. They’re reserved for people who know they exist.
They give strategically through Donor Advised Funds, which let you contribute assets now, take the deduction now, and distribute to causes over time. At a certain scale that becomes a private foundation. They diversify across asset classes most people never touch: private equity, alternative investments, real estate, and often multiple vehicles structured across generations.
Some of this is genuinely accessible. Some of it is not. The how and whether any of it makes sense for your specific situation is a conversation worth having with your financial planner or accountant, not a FinFluencer with a ring light.
Managing Serious Wealth is Not a Passive Activity
It requires attorneys, accountants, financial planners, investment managers, insurance specialists, and often dedicated family office staff. The coordination alone is a job. The decisions are constant. The complexity grows in proportion to the asset base.
I read about Taylor Swift’s engagement, Jeff Bezos’ wedding in Italy, Warren Buffett’s retirement. I follow these stories through a financial planning lens: what does the prenup structure look like, what are the business implications, who’s outraged and why. But I watch from a distance, following the same way I watch a movie. Interesting to observe. Not my life.
In over twenty years of doing this work, I have never once heard a client say I want more complexity in my life. We are all, uniformly, already short on time. The question is never just whether a strategy could work. It’s whether the return on that complexity, in dollars, yes, but also in time and mental energy, is worth it for the life you’re actually living.
For most people, it isn’t.
Comparison and Influence Are Not the Same Thing
There’s a meaningful difference between being influenced by what the wealthy are doing and comparing yourself to them.
Comparison is the thief of joy. That one gets attributed to Teddy Roosevelt, though whether he said it or not, it holds. When we compare, we tend to focus on what someone else has that we don’t, rarely on what we have that they don’t. It doesn’t usually end in warmth. Sometimes it ends in guilt for having more than. Whether we’re at a deficit or a surplus, comparison doesn’t tend to bring the warm fuzzies. If we’re comparing ourselves to the 1% and wanting what they have, that doesn’t leave anyone feeling good. And it brings in a sense of “never enoughness.” Which, as a parent, partner, friend, daughter, and in general a human, feeling like you’re “never enough” or “never” going to get there isn’t on a top 10 list of motivating traits. In fact, it’s one of the fastest ways to slow your progress.
I see my son do it at taekwondo every week. He’s watching the instructor and then all of the sudden he’s looking at the kid next to him and how he’s doing the moves. And of course, the kid isn’t doing them right either so then my son is copying this kid and now they’re both doing it wrong. Fast forward to the end of class where he’s upset when he doesn’t earn a stripe on his belt and gets grumpy because his sister did. It doesn’t matter how many times my husband and I tell him to focus on himself. It’s a rinse and repeat cycle.
Being influenced, though? That can be useful. When it’s thoughtful.
The moments when we pause and ask “is this actually relevant to my life?” are the ones that matter. When I follow a woman on social media who is speaking out for her values and it motivates me to do the same. When I read a substack from a friend about the power of questions in conversation. When I see that every food item on the planet now has protein in it and I wonder if I’m now supposed to get my matcha latte from Starbucks with protein because for some reason they keep pushing it on me. (But, please, tell me why this is happening?).
We are being sold something during nearly every waking hour. We are being influenced online every minute we spend there. The ability to stop and evaluate what issues or topics apply, how we feel about it, and then ensuring that if we do act, it’s out of alignment versus out of “should” is more valuable than whatever tool or product is being shown to us.
What Are You Actually Looking For?
When we look at the 1% and think must be nice, it’s worth pausing to ask: is it? More money doesn’t automatically produce more peace. We don’t see what happens behind the scenes. The family tensions. The legal structures that need constant management. The decisions that have no clean answer. The infrastructure required just to hold what they’ve built.
So when my client asks me every six to twelve months what the 1% are doing, what is she actually asking? What are any of us asking?
Sometimes it’s intellectual curiosity. Sometimes it’s genuine strategy. But a lot of the time, if we’re honest, it’s something closer to: when will I be free? When can I put this down? I’m in a tough season. How do I reduce the weight?
It’s not really about the 1%. It’s about wanting someone to look at your specific life and say: you’re going to be okay. Show me that it will be okay.
And underneath even that is something quieter. Not necessarily the desire to actually put it all down, but the desire to know that you could. That the eject button exists. That exit stage left is an option, even if you never take it. There’s something genuinely settling about knowing the door is there, whether or not you ever walk through it.
What I’ve watched over the years, though, is that even for the people who have clearly earned that exit, who have done the work and hit the numbers and built the foundation, getting to a place where they can actually use it takes time. It takes self-reflection. It takes being honest about what the weight is really about, and whether more strategy is actually going to lift it. Often it isn’t. Often the work is personal, not financial.
That doesn’t mean you stop planning. It means you stay honest about what you’re planning for.
Related: Seven Financial “Tabs” Are Draining Your Wealth. Here’s How to Close Them