In recent weeks, a collection of economic data and explanations of structural forces preventing important things like housing affordability, household formation and economic mobility have provoked many responses—some thoughtful, some angry, some even defensive, but increasingly urging me to look beyond the reliable generational framing.

“Your article is gross,” one wrote to me.

“There is no balance in the world we live in!” another said, adding, “a golf ball is a golf ball no matter how you putt it.  So is the economy!  Adapt!”

Another gave me a sense of the angst felt when broad macro strokes don’t capture the reality on the ground for every micro-case: ” You write like every boomer is sitting on a McMansion and a seven‑figure IRA,” one bereaved Boomer wrote to me. “A lot of us are one bad diagnosis away from losing everything.”

Still another wasn’t much of a hater at all, but wrote with wistfulness about what’s gone down. “Many boomers are poor, scared, and anxious about the life they have left,” they wrote. “They were led to believe that if they worked hard and climbed the corporate ladder you would eventually be able to be financially secure and retire at 65 and enjoy their ‘golden years.’ Many tried this approach but ran into misfortune along the way.” Either there was a layoff at 55 to 60 years old, unanticipated health issues, or others. 

“Life happens. For many boomers, the golden years are not golden, and they don’t have much to look forward to. Their bodies are broken and they are still in debt. They are trapped in a life without a way out and their future does not look golden. Yes, they live longer, but for too many of them, not better and certainly not in a way they expected when they were younger.”

It speaks to the very real sense many Boomers have that things weren’t supposed to end up like this. The generation that rode cheap college, rising home prices, and the 401(k) revolution into late career was expected to bow out gracefully, freeing up houses and jobs for their kids and grandkids. Instead, millions are hanging on—staying in big homes they can’t quite afford to leave and in jobs they can’t quite afford to quit—because they’re confronting a grim reality: in financial terms, they are broke and living too long.

A generation that can’t afford to retire

Roughly 30 million “peak boomers” are turning 65 between 2024 and 2030. Two‑thirds of them will not be financially prepared to maintain their pre‑retirement lifestyles, according to an analysis by ALI Retirement Income Institute economist Jason Fichtner and colleagues that modeled their assets, expected lifespans, and spending needs. More than half have $250,000 or less in retirement savings—before health shocks, market downturns, or long‑term care—which means they will lean heavily on Social Security and work income to get by.

Vanguard’s research on “young baby boomers” reaches a similar conclusion from a different direction. Only about 40% of workers in their early sixties are on track to sustain their standard of living in retirement; the typical near‑retiree faces about a 24% income gap, roughly $9,000 a year. Other surveys find that nearly half of boomers have less than $100,000 saved and about a quarter have nothing set aside at all, despite being at or near traditional retirement ages. For a generation that could easily spend 20 to 30 years in retirement, the math does not pencil out.

Dan, a 71-year-old who retired in 2021, wrote to me of his “head-down and plow-in-the-dirt mentality,” claiming he never missed a day of work in 18 years at a mechanic shop (third shift.) But in the past two or three decades, “we all (not just Baby Boomers) saw our spendable income shrink. How far is it going to shrink? No one knows. Not only that, many of our benefits have been substantially reduced or completely taken away.”

Although it’s true that he has acquired what look like “substantial bank accounts,” he worries about assisted living costing $10,000 a month. “No Baby Boomer wants to be in that situation but it is always in the back of our minds.” The only recourse is to keep working or to hang onto what they worked for — there is no choice about passing on wealth to the next generation when the economy feels precarious.

Dan gets at the core mismatch. A Stanford Center on Longevity analysis notes that a healthy 60‑year‑old woman today has more than a 50% chance of living to 90 and roughly a one‑in‑three chance of reaching 95; men aren’t far behind. Yet surveys as far back as the mid‑2010s found that only about 30% of workers aged 55 and older had accumulated $250,000 or more in retirement savings, even as actuaries were projecting 25‑ to 30‑year retirements as increasingly common.

Even if Boomers planned well for retirement, then, how could they plan for an explosion in lifespan and cost-of-living crisis? A widely cited survey from the Indexed Annuity Leadership Council found that 60% of boomers thought they needed less than $1 million to retire comfortably, and large shares underestimated their likely lifespan and overestimated their Social Security benefits. That combination—optimism about benefits, pessimism about how long they would live—helped produce a cohort that, on paper, owns more wealth than any in history, but in practice includes tens of millions of people who will struggle to finance the last third of their lives.

Stuck in big houses

The housing market is where this financial anxiety becomes concrete. Boomers and older Gen Xers own a disproportionate share of the nation’s three‑bedroom‑plus homes, including many in desirable urban and suburban neighborhoods. They bought those houses when prices were lower and interest rates were modest; many now hold mortgages with rates below 4% or own their homes outright.The reason boomers don’t move isn’t just sentiment—most boomer homeowners (about 54%) have no mortgage at all, so there’s little financial pressure to sell. A Redfin analysis of 2024 Census data found that empty-nest baby boomers (one- to two-adult households) own 28% of U.S. homes with three or more bedrooms, compared with 16% for millennial households with kids.

Housing economists talk about a “mortgage lock‑in” effect: when you have a low fixed rate and a large unrealized gain, selling and buying even a smaller place can raise monthly costs once you factor in today’s higher rates, taxes, and fees. That’s exactly what many older homeowners describe. A couple in Phoenix wrote that they “cannot afford to sell our home and move,” noting that one‑bedroom apartments now rent for more than their mortgage and that senior living facilities are out of reach. “We are not rich, just comfortable at the moment,” they said—emphasis on “at the moment.”

This attitude extends down to generations, based on a darkly funny exchange I got with a certain Gen Xer. “I do live in a 6400-sq-ft house with a $3 million view that’s paid off. I just want to say that if my continued existence can possibly make any younger people more miserable, broke, and whiny, then it’s all worth it. Sincerely, a Gen X who worked hard and has no problem with the younger generation paying high rent for crappy apartments while they build zero equity.  Did you hear that sound? It was my heart breaking for the younger generation(s) (not).”

When I followed up to ask why younger generations seem whiny, I got a nice picture of that $3 million view, and the explanation, “I have no idea, but anytime I go on social media young people are complaining about their inability to buy a house or a car. I worked seven days a week most of my life for what I have; no one ever heard a single complaint out of me and they never will. And for the record, I am a hard-core liberal Democrat and always have been.”

An unequal pig in the python

None of this is evenly distributed. Wealth data show extreme inequality among older Americans: early work using the AHEAD survey found that households with someone 70 or older in the top tenth of the wealth distribution held around 2,500 times as much wealth as those in the bottom tenth, and more recent work finds that inequality has widened further since the late 1990s. Older Black and Latino households, renters, and those with chronic health conditions are far more likely to enter late life with low assets and high debt.

The letters reflect that divide. At one end is the anxious, under‑saved retiree doing everything possible to stretch limited assets. At the other is the California homeowner who bought for just over $1 million and now sits on a home worth more than $4 million—but worries that selling would trigger close to $1 million in combined federal and state taxes. In the middle is a broad group that describes itself as “fine, but not secure” and treats staying in place—physically and professionally—as the only rational option.

A system built for shorter lives

It is easy to frame this as a morality tale about selfish boomers strangling the economy they built by refusing to move or retire. The reality is more structural, and in some ways more damning. Over several decades, the U.S. shifted retirement risk from employers and the state onto individuals just as lifespans were lengthening and housing and healthcare costs were exploding. Defined‑benefit pensions gave way to 401(k)s; long‑term care remained largely uncovered; tax and housing policy rewarded holding onto appreciating property rather than making room.

Boomers largely followed the script they were given: work hard, buy a house, save in tax‑advantaged accounts, rely on Social Security to fill in the gaps. Many are now discovering in their late 60s and early 70s that the script did not account for a 90‑plus lifespan or for the cumulative effects of wage stagnation, market crashes, and runaway medical costs. Seen from the outside, they look like a wall of retirees hoarding houses and jobs; seen from the inside, they look like a generation quietly terrified of running out of money before they run out of years. To then be blamed for this structural issue, instead of recognizing its reality, seems a bridge too far.

A 69-year-old real-estate consultant wrote to me to say that this reporting echoes conversations he often has with his two millennial children and five millennial nieces and nephews. “I have systematically and factually compared my affordability when I bought my first house with them,” he wrote. “In every analysis, the cost of homes were less, interest rates were much higher, the quality of the homes and the areas I could afford were not close to what they want.” Most millennials, he argues, are unwilling to do what needs to be done to get a house,” whether that’s save more to buy a house in a nicer neighborhood or pursue a house somewhere less fashionable. Overall, the added, this is “not a generational issue (though that’s is one the influences), but one of economics. It’s the sheer number of Boomers that creates the problem you describe, not the Boomers themselves.”