[GUEST] When the Path to Homeownership Slips into the Upside Down

Another banger from Summer Goralik

Ever tried to write about a problem you’ve lived, but can’t fully grasp? You feel its weight, know it’s serious, yet can’t trace its edges or its origin. It’s just that complicated.

When you start to imagine solutions, or more likely the many solutions, the problem only grows heavier. In the end, it feels less like a puzzle and more like a battle already half-lost.

The problem I can’t shake? Housing affordability. And even though I’ve managed to buy a home, I’ve also felt the sting of its absence and carry the lingering awareness of how narrowly I avoided being priced out.

I’m no economist or housing data expert. I’m speaking from a different mountaintop. From what I’ve seen, read, and lived, I know this: the system we built, the one meant to transform hardworking people into homeowners, may be crumbling under its own weight.

Oh, and when I say “system”? That’s my cue to share a different kind of housing affordability story. Not another policy brief, not a data-heavy report, but a narrative—part lived experience, part science fiction (yes, believe it or not). Sometimes the only way to grasp hold of a problem is to pin it down differently, from an unexpected place. With that, I think we begin here.

If you’ve seen the Netflix series Stranger Things, a television show set in the 80s, then you know the Upside Down, an alternate dimension that mirrors our world. The same streets, the same homes, the same landmarks exist, but everything is twisted. Cloaked in darkness, choked by vines, and crawling with danger. It looks familiar, but distorted and hostile.

Being a longtime fan of the show, a wild blend of sci-fi, horror, and 80s drama, the parallel I’m about to draw didn’t arrive politely; it crept out of the shadows and tapped me on the shoulder in true scary story fashion.

Like the Upside Down, today’s housing landscape and the pursuit of a home feel eerily similar: heavy, even crushing at times, particularly for younger generations. On the surface, the world looks much like it did fifty years ago, but beneath it, progress has stalled.

Far fewer are crossing that threshold into homeownership. Generational wealth now acts like a winning lottery ticket, while hard work alone rarely buys entry. Without that head start, the weight of student loans, rising living costs, and stagnant wages has twisted the road to affordable housing into something nearly impossible to find.

The new baseline? Veering off course, into unforgiving terrain, a version of ownership harsher than the one generations before us experienced.

The Upside Down didn’t just appear overnight. Its roots crept in slowly, growing thicker and sprawling wider year after year, shifting the ground beneath us and warping the once-stable image of homeownership. You know the picture. The white picket fence, the modest starter home, the promise of stability and belonging.

But today that portrait feels more like a mirage that young people and many others keep chasing, even as it drifts further out of reach, fading into the shadow.

The very system that told young people to “get an education and work hard” is now the one pulling the housing ladder up behind them. If we’re not careful, the dream of homeownership — the promise that once anchored generations — could be swallowed by its harsher inflection: not the American Dream, but an American nightmare.

That’s where our youth find themselves today. Not climbing toward a brighter future, but wandering the Upside Down of the housing market.

For What It’s Worth…Here’s My Own Path

I didn’t buy my first home until I was 34. My husband and I rented for years, waiting and saving. At one point, we even lived in a tiny apartment directly under the runway at LAX, so close that airplane headlights lit up our living room. It was far from glamorous, but it was cheap, and it kept us on track toward a down payment. Somehow, those headlights always made us laugh.

Like many, we even moved back in with our parents to save money. It wasn’t easy, but it was necessary — and today it’s often the only way forward. By the time we finally took the leap, I was pregnant, which added urgency to our decision, a pressure many families recognize.

Buying later shaped not just where we lived, but when and how we started our family. Homeownership delays often mean family-building delays too, a reality that quietly haunts more households than most policymakers care to admit.

We ended up purchasing a home in a cheaper area, not where we had imagined planting roots, but where we could make the math work. Looking back, I sometimes wonder what would have happened if we had traded a nice wedding for a bigger down payment. That single choice might have bought us stability years earlier.

Meanwhile, friends of ours were getting a very different start. Some inherited homes outright. Others had parents purchase homes for them, or gifted them full down payments. For some, the help came earlier, with college tuition fully covered or student loans erased, freeing them to save aggressively for their first house. Others walked straight into family businesses out of high school or college, with security and career growth built in from day one.

Their launch pads looked nothing like ours. And while I sometimes ask myself if what I feel is envy or jealousy, I remind myself to stay focused on my own journey. No one can take away my work ethic, which my son now sees firsthand.

I share my story not because it’s unusual, but because it isn’t. We’re not operating in the same housing market our parents knew. At first glance, it looks unchanged, but the rules are warped and the foundation is broken. And just like in Stranger Things, people are stuck in the Upside Down of homeownership, where the light of the American Dream still flickers, but too weak to guide the way.

My experience is only one thread. The numbers tell an even starker story.

The Roots of the Upside Down

To escape the Upside Down, or simply get unstuck, you have to start at the roots. And in housing, those roots are complicated, they run deep and form a web of adversity.

One root is financial literacy, or rather, the lack of it. Too many of us enter adulthood without knowing how to manage credit, debt, savings, or even the real cost of interest. Credit card firms, of course, exploit this, especially on college campuses where few are thinking about homeownership. These gaps deprive us of stability in our 20s and leave us scrambling in our 30s, inevitably delaying family-building too.

Another root is grounded in the relentless rise in home prices. Rob Hahn has argued that high home prices aren’t a win if they slam the door on the next generation. And the National Association of Realtors’ latest 2025 Housing Affordability & Supply Report delivers sobering confirmation: A household earning $75,000 a year, a once seemingly solid middle-class income, can now afford barely one in five homes on the market. Before the pandemic, it was closer to half.

Realtor.com echoed the trend in its own analysis. “At 2019 mortgage rates, the typical U.S. household could afford a home priced around $325,000. Today, that number has dropped to about $298,000, despite the higher income.” Meanwhile, the median-priced home has surged 38% to $439,000. Put simply, a middle-class income now buys far less.

These numbers aren’t abstract. They come with real faces, real lives. This troubling data represents young people and families whose plans are stalled, whose futures are put on hold. Not surprisingly, this is how the Upside Down operates. Opportunity looks attainable, but fades the closer you get.

Then there’s lending, the supposed lifeblood of housing. Economist Richard Werner, whose work I first encountered through Rob’s recent post, argues that mortgage-driven credit doesn’t grow economies; it inflates prices.

I saw this firsthand during the mid-2000s collapse while working in escrow, watching buyers walk away from closings with 100% financing, keys to the house, and even the return of their earnest money deposits. It felt wrong, and it was. Werner’s theory, echoed by Rob, is compelling. Unless credit is redirected toward building real supply and supporting genuine economic growth, we’re planting the seeds for repeat disasters. More roots.

Even the houses themselves bear witness. As Fortune put it, we’re living through “housing shrinkflation.” New homes are 11% smaller than a decade ago yet 74% more expensive per square foot. Classic Upside Down logic. It looks the same, but offers less. And when less costs more, buyers are tempted by shortcuts.

As James Rodriguez wrote in Business Insider, builder-funded rate buydowns offer the promise of relief, but it’s a fragile facade. The payments reset, the reality returns, and too many are left stuck in “upside-down” investments, quite literally.

Finally, though hardly the last, there is generational wealth, one of the deepest roots of all. Andrea Riquier’s recent USA TODAY investigation into heirs’ property shows how fragile that wealth has always been for many Black families. She tells the story of Saul Blair, whose great-grandfather, born into slavery, managed to acquire more than 300 acres of farmland in Georgia—land his descendants have spent decades trying not to lose.

Examining these issues is a powerful reminder that land and homeownership have long been vulnerable to theft, exploitation, and systemic neglect, with racial discrimination leaving a legacy that still shapes housing today.

Have you heard enough? These are only a few of the roots. There are others, too, entrenched and tangled like a network of wires inside a computer. Cutting them won’t be easy, and there’s always the risk they’ll grow back.

And here’s the thing: when it comes to housing affordability, many will fight only for their own families. That is human nature; we see the world most clearly through our own eyes. But what we need, and what we owe, are leaders willing to fight for all families, for all people.

Waiting for the Wake-Up Call

So what will it take for change? To attack the roots that keep homeownership out of reach? Are local, state, and national groups, even those outside real estate, willing to advocate for younger generations?

Too often, housing affordability only rises to the surface when those in power feel the pain themselves. When their children graduate into a job market that can’t cover student loans, struggle to save for a down payment, or realize that the American Dream they were promised has skewed into something closer to a nightmare. That’s when they see their own families trapped in the Upside Down.

I think about it the same way I once thought about deed fraud. When I was tracking it, I was baffled by the lack of urgency. Title records could be twisted with false filings, throwing homeowners and courts into chaos, yet the issue has remained low priority. I often theorized that reform would only come when it hit closer to home — when a legislator, a judge, or a CEO became a victim.

Housing affordability feels the same. Unless those in power see their own families locked out, the wake-up call may never come, or comes far too late.

Tell me I am wrong. Be the one who wakes up and makes a difference.

Let’s Get Back to the Right Side

Housing affordability is not just about homes. It’s about futures. And this is precisely why it’s so fundamental. We must decide whether homeownership remains a cornerstone of opportunity, or risk slipping further into the Upside Down, where only a few can ever find their footing.

I didn’t have generational wealth to fall back on. I had grit, and realistically, good timing. But grit, as I’ve tried to show, is no longer a guarantee. What it will take is more than individual determination. It will take institutional change, economic recalibration, and leaders willing to write new prescriptions for policy and reform.

Rob is right. The industry must stop treating high prices as a win and start fighting for real affordability. And schools, associations, legislators, communities, and regulators need to step up with earlier financial education.

The good news is, we are not powerless. Change begins with voices, with discussion that sparks advocacy, with advocacy that grows into action. We need to do more than patch holes. We must reimagine the entire plot and rebuild the path to ownership for all.

If we do, then generations to come won’t be stranded in or strangled by the Upside Down. They may never know it at all. Instead, let them know only the light — building futures, creating wealth, and living on the right side of the Dream.

The American one.

-Summer