I've been having the same conversation with my clients for the past year, and it's not the one you'd expect.
These are people who are doing great. Their 401ks are up. Their home values, especially here in Houston, keep climbing. They haven't been laid off. They got their bonuses. By every objective measure, they're winning.
But they're anxious as hell.
The K Economy Hits Different When You're on Top
For the first time, my upper middle-class clients are actually seeing themselves as upper middle-class. They're recognizing they're in the "have" category of what I call the K economy. This bifurcated reality between those with assets and good jobs and those without.
And they're starting to feel guilty about it.
They go to the grocery store and think, "Thank god we make a lot of money because I don't know how people are affording this." They see the prices. They feel the inflation. But it hasn't crushed them like it's crushing other people.
This is new. This awareness is new. And it's causing real confusion.
The Three-Legged Stool
My clients have come to a sobering realization: their success rests on three legs.
They got into a house when it was affordable. They got into the stock market. They've had stable employment.
For the first time they realize if they lost any one of those three legs? They'd never get back to where they are now.
That's the fear with a side of guilt that's keeping them up at night.
It used to be, "Jon, I only got ten more years until retirement." Now it's, "I'll never enter this job market again at this level. If we lose this home, we’ll never be able to buy in again."
I'm seeing people fight for their marriages and their jobs in a new and different way because they really feel like if they lose this advantage, this momentum they have in being on the upper part of the K, they can't catch back up.
They Got Lucky (And They're Starting to Admit It)
Boomers and late Gen Xers (I'm an early Gen Xer) are finally recognizing the wave of opportunity they rode to get where they are. Even though they'd consider themselves bootstrappers, they can now see it so clearly. They rode an economic wave to these heights.
They survived the dot-com boom and bust. They got into housing before it became impossible. They built 401k balances during one of the greatest bull runs in history.
Yes, they worked hard. Yes, they made good decisions. But they also got a little bit lucky with timing.
Now they're watching their own children try to enter this economy, and they're seeing it's a completely different game.
The Sandwich Generation's Impossible Choice
This guilt is manifesting in real financial decisions. My clients are writing checks for their adult children in ways previous generations didn't. And they're split into three camps:
- The Overgenerous: They're helping so much they're enabling. Their kids are never going to emancipate because mom and dad keep swooping in. It's an enmeshment that's not healthy for anyone, but they feel so guilty about the economic reality their kids face that they can't stop.
- The Undergenerous: These folks are going to Italy while their kids are literally struggling. They're going to die with millions of dollars when a little help and support along the way would have just evened things up. They stick to the "I had to do it on my own" mentality even though the economic landscape has fundamentally changed.
- The Stuck: They give a little to one kid. Do they give to the other? They don't know what to do, so they're paralyzed. They want to help, but they're terrified of being unfair or creating dependency.
Meanwhile, they're also supporting aging parents. Classic sandwich generation, except now with the financial means to actually do it and the crushing awareness of how much it costs.
My Advice: Don't F*ck It Up
So what do I tell these anxious, guilty, successful clients?
Do not get desperate. Do not swing for the fences. Do not change the strategy that got you here.
The pillars of this economy - the pillars of what has worked to get them here - have not shifted or changed. They are going to survive AI just like they survived the internet revolution. What has made them successful in relationships at work and in the community is still going to be effective. The fundamentals of showing up, adding value, being someone people trust and want to work with? That doesn't get disrupted.
They do not have to significantly change. But they do need to stay curious. Keep their skills sharp. Maybe learn a few new ones - not because you're about to be replaced, but because engaged people stay relevant. Keep networking. Update LinkedIn. Get that certification they've been putting off. Stay current on the job skills that matter in their industry. It's not over until it's over, and too many people start coasting at 52 like they've already crossed the finish line. They haven't. The ones who get left behind aren't the ones who didn't learn the newest software; they're the ones who stopped being interested in learning anything at all.
I think part of this fear is an age thing. People think the world is moving faster. It's not moving any faster than it was. It just feels like it's moving faster because our brain is slower.
So be okay with being in the top part of the K. Don't f*ck it up.
The Real Question
When my clients come to me with an open-ended question about their portfolio, what they really want to know is: Am I going to be okay?
And I'm willing to have a deeper, more complicated, more nuanced conversation about what their fears actually are. Is it related to their own health? The cost of supporting an aging parent? Supporting children through college or early adulthood when they weren't anticipating it?
Because they're doing great, but they can see now how precarious even this privileged position is. They can see how the middle class is shrinking. They can see how hard it would be to climb back up if they fell.
That awareness doesn't mean they are doomed. It means they're paying attention. And paying attention, having these honest conversations about money and class and opportunity, that's the first step to not f*cking it up.
Come talk to me about these fears. Let's make sure you stay in the have category. And let's figure out how to help the people you love without enabling them or abandoning them.
That's the work now.
Jonathan Kolmetz is a Licensed Professional Counselor, Financial Advisor, and President of Oaks Wealth Management. He holds an MBA, a Master's in Clinical Mental Health Counseling, and specializes in the intersection of family psychology and wealth planning. If your family is navigating the complexities of multi-generational wealth transfer, we invite you to explore how our unique approach combines financial expertise with family systems understanding.