Family Update
Grammy, Pop, my sister, and her boyfriend came to town to celebrate Chris's big graduation day. My sister and her boyfriend turned it into a beach vacation, staying down on Lido Key. While relaxing on the beach toward the back row of chairs, the front row suddenly erupted in chaos, with beachgoers leaping up and racing toward the hotel in full terror. My sister frantically scanned the water. A shark? A tidal wave? No. It was love bugs. A swarm of love bugs descended on the beach, sending an entire row of unsuspecting vacationers fleeing in panic, leaving my sister going from pure panic to complete bewilderment. There are no love bugs in Pittsburgh.
We attended Chris's graduation banquet and graduation ceremony, where each teacher took a moment to speak about their students, which sounds like it could go on forever, but with only 25 students in his class, it was actually a really lovely and personal touch. There was also a photo slideshow featuring each student, with pictures the parents had supplied from childhood on up, which was equal parts adorable and nostalgic.
I'm 49. That puts me squarely in Gen X, which means I'm old enough to have bought a house before things got insane. Old enough to remember eggs costing $2 a dozen. Old enough to find a job somewhat easily out of college.
So when I look at what younger people are dealing with right now, I don't see entitlement. I see a system that's gotten genuinely harder to break into. And a lot of the reasons why aren't exactly anybody's fault. They're just the math.
Let me walk you through it.
The Housing Thing
The median homeowner in the U.S. has now lived in their home for nearly 12 years. Back in 2005, it was 6.5 years. Homes are turning over at roughly half the rate they used to. A big reason is older homeowners staying put. Which makes complete sense from where they sit. More than half of boomer homeowners own their homes free and clear, with a median monthly cost of ownership, including insurance and property taxes, of just over $600. Why would you give that up to go sign a 7% mortgage? You wouldn't. Nobody would.
But here's what that's doing on the other end. The U.S. housing market was short 4.9 million units in 2023 relative to the mid-2000s. And younger buyers are fully absorbing that shortage. The median age of a first-time buyer has hit 38, a record high. In the 1980s it was the late 20s. That's a full decade of lost equity accumulation. A decade of not building the thing that, for most Americans, is their primary source of wealth.
First-time buyers now represent just 21% of all purchases, the lowest share since the National Association of Realtors began tracking data in 1981.
Lowest ever recorded. That's not a blip.
The Market Thing
A rising stock market is great news if you have money invested. For retirees with portfolios, the last several years have been a genuine gift.
But here's what doesn't get said often enough. Corporate earnings that drive stock prices are frequently the result of companies doing more with fewer people, keeping wages lean, and extracting greater productivity from workers with few options. The market going up and younger workers struggling aren't always unrelated. They can be two sides of the same equation.
And if you don't have money in the market yet, a rising market doesn't help you at all. It just makes everything feel further away.
The Savings Problem
Here's why younger people aren't building wealth. Recent graduates are earning an average of $68,400 while carrying about $94,000 in personal debt. That's before rent, food, transportation, or health insurance. The math is genuinely brutal, and it's not a mindset problem.
About 58% of students who graduated in the past year are still looking for their first job, compared to just 25% of prior graduates from older generations. That's not laziness. That's a hard landing on top of an already expensive world.
Now Add AI
This part is new, and it's moving fast. Postings for entry-level jobs dropped 35% from January 2023 to June 2025. AI is a major reason why.
What makes this particularly lopsided is how AI actually works in the labor market. AI is very good at replicating systematized knowledge, the kind you learn from textbooks. It's much less capable of replacing tacit knowledge, the kind that only comes from years of experience. So it tends to replace people just starting out and make those with decades of experience even more valuable.
A Stanford study found that since late 2022, employment among workers aged 22 to 25 in the most AI-exposed jobs has fallen by about 6%. Older workers in those same roles saw gains of 6% to 9%.
The people already established are getting a tailwind. The people trying to find the door are finding fewer doors.
So What Do I Do With This?
I'm not writing this to stir up generational resentment. Most of my clients are older than me and they've done everything right. They saved, they were patient, and they deserve what they've built.
But if you have kids or grandkids in their 20s or 30s, this is the world they're actually living in. It's not in their heads. The data is real.
Be Blessed,
Dave
P.S. - In my newsletter last week, I talked about a transfer-on-death deed. Several readers pointed out to me, and they are correct, that in Florida, it is called a ladybird trust. It does exactly the same thing, but in this state, it's just called something different.
P.P.S.- Thank you to all of those who subscribed to Dave's Orchid Oasis YouTube channel. I crossed the 10,000 subscriber threshold! My kids are in awe.