Portfolios up. Home values up. Bonuses paid, jobs intact, and by every conventional measure, my clients are winning. And they are anxious as hell.
Something has shifted, and it is not the portfolio.
What I am seeing in my practice right now is not ordinary retirement anxiety. My most successful clients have arrived at a specific and unsettling realization: the three things that built their financial lives, getting into a house, getting into the market, and holding stable employment, cannot be replicated at today's prices, rates, and conditions. They are not just worried about losing what they have. They are worried that if they lose it, it is gone for good.
They Can Finally See The K
For the first time, my upper-middle-class clients are actually recognizing themselves as upper-middle-class. They are seeing that they are in the "have" category of what economists have called the K-shaped economy. Think of the letter itself. The top line keeps climbing: assets grow, portfolios rise, professional salaries hold strong. The bottom line angles down: wages stagnate, housing becomes unreachable, and basic necessities eat a bigger share of every paycheck. What has disappeared is the middle, the path that used to connect the two.
My clients are on the upper line, and for the first time, they are really seeing it and feeling guilty about it. They go to the grocery store and think, thank god we make good money, because I genuinely do not know how other people are affording this. They see the same prices everyone else sees and feel the same inflation, but it has not crushed them the way it is crushing other people. That awareness is new, and it is causing real confusion.
The Three-Legged Stool
My clients have figured out that their success is sitting on three legs. They bought a house when that was still possible. They got into the market. They have had stable employment. And for the first time, they are realizing that if they lost any one of those three things, they would not be able to get back to where they are now. That is the realization that is keeping them up at night.
I am hearing things like, "I will never re-enter the job market at this level. If we lose this house, we are never buying back in."
It is not staying contained to financial conversations either. People are fighting harder for their marriages and showing up differently at work, because they feel, really viscerally feel, that if they slip from the upper part of the K, they cannot claw their way back up.
They Got Lucky (And They're Starting to Admit It)
Boomers and late Gen Xers (I am an early one) are starting to see the wave they rode to get here. They would call themselves bootstrappers, and they are not entirely wrong, but they also worked hard, made decent decisions, and happened to time everything right in a way that simply is not available to the people coming up behind them. They survived the dot-com bust, bought housing before it became effectively impossible for a new buyer, and built their retirement balances during one of the greatest bull runs in history.
Now they are watching their kids try to enter this economy and seeing that it is a completely different game.
And that gap, between the economy they built their lives in and the one their children are inheriting, is exactly where the guilt lives.
The Sandwich Generation's Impossible Choice
The guilt is showing up in real dollars. My clients are supporting their adult children in ways that previous generations flat-out did not, and they tend to fall into one of three camps.
- The Overgenerous: Some of them cannot stop swooping in every time there is trouble, and their kids are never going to develop real independence because of it. It is enmeshment dressed up as generosity, and they know it. They just cannot stop because the guilt about the economic reality their kids are facing is louder than everything else. What I see down the road is adult children who have never had to fully commit to anything, because the safety net always appeared before the consequences did.
- The Undergenerous: Then there are the ones booking trips to Italy while their kids are genuinely struggling, who will die with millions of dollars when a little well-timed help along the way would have simply evened things out. They hold onto the "I had to do it on my own" mentality even though the economic landscape they did it in does not exist anymore. The ones who hold this line the longest tend to realize too late that the money they protected so carefully did nothing to protect the relationship.
- The Stuck: Lastly, there is the paralyzed middle. They are the ones who give a little to one kid and then freeze completely because they do not know if they should give to the other, so they end up doing almost nothing while the anxiety compounds. The paralysis itself becomes the decision, and usually the kid who needed help the most is the one who got the least of it.
Meanwhile, most of them are also supporting aging parents at the same time, which makes it the classic sandwich generation situation, except now they actually have the financial means to do it and the front-row seat to exactly how much it costs.
My Advice: Don't F*ck It Up
So what do I tell these anxious, guilty, successful clients?
The first thing is to have the actual conversation, not the sanitized version they give at dinner parties, but the real one, with someone they trust enough to say, "I am genuinely scared that we could lose this and never get it back." That conversation does not have to happen with a professional. It can be a close friend, a spouse who is finally ready to engage, a sibling who is in a similar position. The point is that financial fear tends to calcify when it stays private, and most people are carrying around a version of this anxiety that has never once been spoken out loud.
The second thing is to actually use the plan you paid for. If you are worried about your cholesterol, you go get a blood test rather than lying awake wondering. A financial plan works the same way, telling you whether your financial life holds up when something goes wrong. That means running real scenarios with your advisor: job loss, a meaningful market correction, a housing value that stops climbing. If you have not had that conversation recently, you are leaving the most valuable part of the relationship on the table. You are paying for the team. Make them earn it.
Beyond that, my advice is simple: do not get desperate and do not start swinging for the fences. The fundamentals that got them here, showing up, adding value, being someone people genuinely trust and want to work with, those are not going to get disrupted by AI any more than they were disrupted by the internet. What they cannot afford to do is coast. Too many people hit 52 and start acting like they have already crossed the finish line, when the ones who actually get left behind are not the ones who did not learn some new piece of software. They are the ones who stopped being curious about anything at all.
A lot of this fear is also, honestly, an age thing. People feel like the world is moving faster than it used to, but it is not. Our brains are just processing it a little more slowly, which is completely normal. Stay interested, keep the network warm, get the certification you have been putting off, update LinkedIn, stay current on what matters in your industry. None of that is about survival, it is about staying engaged, and engaged people stay relevant.
So be okay with being in the top part of the K. Do not f*ck it up.
The Real Question
When a client comes in with an open-ended question about their portfolio, what they really want to know is whether they are going to be okay. So I have gotten comfortable having a deeper, more complicated conversation about what their fears actually are, whether it is their own health, the cost of a parent who needs more care than they planned for, a kid who needed support they were not anticipating, or the quiet fear that the marriage or the job or both are not as solid as they look on paper. We talk about the things actually holding the stool together, which might not be as solid as they appear.
They are doing great, and they can also see clearly how precarious even this privileged position actually is. They can see the middle class shrinking and they understand how hard the climb back up would be if they fell. That awareness is not a sign they are doomed. It means they are paying attention, and paying attention, having these honest conversations about money and class and luck and fear, is the first step to not blowing it.
If you recognized yourself somewhere in this piece, that is probably not an accident. Come talk about what is actually keeping you up at night, and let's find out together whether the fear is louder than the facts.
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.