I often tell my students that if they don't look back on themselves five years ago and feel a bit embarrassed, they're not growing as people. I'm having one of those moments this week. Over the last year or so, I’ve finally come to understand the centrality of housing affordability to what ails the US. 

I've had conversation, after conversation, after conversation, on the podcast about housing. But I treated housing like a side project or intellectual curiosity, rather than understanding it is the key challenge  facing modern society. 

But I finally got it. God bless my wife for putting up with me. I can be so thick-headed sometimes.

If you don't have a door that locks where you can safely secure your belongings it's nearly impossible to engage on an equal footing in society.

It robs people of a sense of safety and security.

It makes getting and maintaining gainful employment nearly impossible over the long-term. 

It deprives people of their dignity.

The traditional personal finance rule of thumb is that families shouldn't spend more than 30% of their income on housing. But according to BLS statistics, for Americans in the second-lowest income quartile, that figure is closer to 45%. For the lowest quartile, it can hit 75%. 

Those aren't abstract percentages. 

Each quartile of the US population is roughly the size of Germany. That means one Germany's worth of households is spending 45% of their income on housing, and another Germany's worth is spending around 75%. Over 160 million people, half the population of the US, are saddled with housing costs that break all personal finance models. 

This is a perpetual misery machine for working families. Combine high housing costs + rising consumer prices due to tariffs + rising gas prices due to a dumb war +  rising food prices due the supply chain issues (and a gutted FDA) = the current moment of seeming national misery.

Sure, some of the things I just listed are transitory. But when those factors wane, rents aren’t coming back down, they rarely ever do.

Not surprisingly as a result, according to this Congressional report, there were just shy of 800,000 people experiencing homelessness in the US on any given day in 2025. And that number is rising, up about a quarter million people since 2019.

I knew all this. But I didn’t know all this. 

I think the anvil that finally dropped on my head about this topic was the convergence of two conversations. The first was my reading of There Is No Place for Us by Brian Goldstone, discussed in the prior newsletter. The second was a conversation with my serial housing interlocutor, Marguerite Martin, on the podcast (see below). It was only when I was making the show notes for that interview that I realized these were the same conversation, and it's a conversation I've been having but not truly understanding for a decade.

And so I'm going to do something different with today's newsletter. Below is a brief annotated bibliography, or a syllabus, about housing and homelessness in the US. Over the next couple of weeks, I invite you to check some of the recs out or share your thoughts about them (if you’ve read them already), and let’s have an ongoing dialogue about housing and affordability in the US:

The Books

There Is No Place for Us. You know this one. Goldstone followed five Atlanta families, all employed, all working full-time, as they slid into homelessness. Not because they were lazy or making bad choices, but because the math no longer worked. 

Evicted. Similar to Goldstone, Desmond embedded in Milwaukee's poorest neighborhoods, following eight families through eviction court. What he found was that eviction wasn't just a consequence of poverty; it was a cause of it. Losing your home meant losing your job, your possessions, your credit, your sense of security. Desmond showed how landlords profited from eviction fees, courts processed evictions like assembly lines, and the housing voucher program was so underfunded that only one in four eligible families received assistance. 

Poverty, by America. If Evicted was the diagnosis, this was the broader argument about why we tolerate the disease. Desmond's central claim was uncomfortable but essential: the rest of us, those who were financially secure, benefit from poverty. We pay lower wages. We get cheap goods. The US welfare state was designed to give the most to those who needed the least: mortgage interest deductions, tax breaks for the wealthy, subsidies for homeowners that dwarf what we spend on housing assistance. 

The Color of Law. Black Americans experience higher rates of poverty and housing instability. That's not an accident or a cultural failing. It's the result of deliberate policy choices. Rothstein explained how housing segregation and the accompanying wealth gaps were engineered. The racial  wealth gap is not a coincidence. The Color of Law tells the story of how that goose was cooked. 

One More Podcast
The Bottom End of the Housing Market Has Been Destroyed. This was my 2021 conversation with NPR journalist Will James about the Merkle Hotel, a last of its kind residential hotel in Tacoma, that closed in 2018, pushing its occupants into the streets. Within three years nearly half the former residents were dead.

In Round 2, coming next week, I will share responses that come in from readers and share some of the other conversations I’ve had about housing, homelessness, and some of the books above.

Thanks for being along for this ride as a thought partner.