What happens when one generation holds much of the country’s housing wealth and has little reason to give it up? Chuck Marohn talks with Strong Towns board chair Andrew Burleson and historic property renovator Richard Rumrill about boomers buying bigger homes, even as younger families wait for those houses to come back onto the market. The generational frustration is easy to understand, but the expected handoff assumes older homeowners will be ready to leave. What happens when the people expected to move have nowhere they want to go, and everyone behind them is still waiting?
The conventional story about aging is that people raise a family, become empty nesters, and eventually downsize by moving into a smaller home. A recent article in The Wall Street Journal titled “Boomers Were Supposed to Downsize; They Are Buying Bigger Homes Instead” suggests that script is changing, at least for the most affluent baby boomers.
Rather than buying smaller homes, many of them are purchasing larger ones or investing heavily in additions and renovations. They’re creating homes designed to host children and grandchildren, accommodate aging in place, and serve as gathering spaces for family and friends. The article argues that this shift is possible because this generation controls an extraordinary share of the nation’s wealth, much of it accumulated through decades of home-price appreciation and rising financial markets.
We’re going to discuss this article, and I suspect there will be a smidge of baby boomer bashing here at the top. I promise we’re going to keep that to a minimum, because I’d like us to move beyond the individual choices being described and think about what they reveal about the housing market as a whole.
What does it mean when the generation that owns most of the country’s large homes is also competing for even larger ones? Is this simply a story about changing retirement preferences, or does it tell us something deeper about wealth, housing demographics, and the way our housing system functions?
Welcome to Upzoned. This is where we take one big story making the news and explore what it can teach us about building stronger towns. My name is Chuck Marohn. I’m the president of Strong Towns, and because I’m going to ask each of our guests to share their age so you have that perspective going in, I’ll say that I’m solidly Gen X. I’m 53 years old.
To help us wrestle with the questions presented in this article, we’re joined first by Richard Rumrill. He’s a historic-property renovator, market researcher, and teacher. Since the 1990s, he’s worked on stabilizing and renovating historic properties, including a colonial-era family farm and duplexes from the 1850s and 1890s. He’s also part of Strong Towns RVA, the Local Conversation based in Richmond, Virginia. Richard, welcome to Upzoned.
Thank you, Chuck. I am 61, which means I am one of the last baby boomers. The generation is named after me, according to some.
I’m very happy that we have a baby boomer, technically a late-stage baby boomer, on the podcast to represent. I won’t put all that burden on you, however, so thanks for being with us.
We’re a diverse generation, that’s for sure.
We also have millennial Andrew Burleson, chair of the board of Strong Towns, a role he’s had since 2014. His work spans urban planning, real estate, financial technology, and publishing. He’s not only a founding visionary for Strong Towns, but a good friend of mine. Andrew, welcome back to Upzoned.
Am I misrepresenting millennial? Would you claim millennialship?
No, I am very happily a millennial. I’m still coming to grips with that meaning middle-aged. I can’t decide if that’s okay or not yet, but I’m 42, so I guess I’m right on that cusp.
I have four kids, and that actually makes me feel more okay with it. I remember being a kid, and by definition the people with all the kids were the middle-aged people. I’m trying to think of it as not an unwelcome milestone. It’s a celebration. It’s a fun time of life. Feeling old is a shared experience that hopefully we all get to have at some point.
Having two kids in college definitely makes you come to grips with the idea that time passes and you become the thing you never thought you would be, which is a little bit older every year.
Andrew, start us off here. I know you had a lot of passion about this article, and it was almost rage bait to you. I want to get your take first before we pass it to Richard and I share some of my initial thoughts.
I’ll let the listeners in on this: I told Chuck I wasn’t sure this was the best topic for me to chime in on because I saw the article before he asked me about it, and it really steamed me a little bit. My wife told me it would be good for me to practice speaking about these issues with restraint, so we’re going to find out if that works.
Part of what we have to face is that journalists want impressions on their stories, and they found somebody to be a very acerbic representative of the boomer generation. Right at the top, we have, “We’ll downsize when they plant me six feet in the ground,” said Victor, age 64. That’s not how normal people talk or think.
If you wanted an avatar of a boomer to be angry at, they found the guy. That’s why this came across my feed. I saw a bunch of people sharing it and being angry at his quote, and it got me a little hot too. But to some degree, we have to stop and say, okay, this is what journalists do. They sell entertainment. Let’s look past that and see what else is going on here.
Richard, what were your initial impressions? How did you approach this article?
I got interested in the idea of someone moving from a 2,000-square-foot house to a 5,000-square-foot house next door. I started to wonder whether they were allowed to do anything with the 2,000-square-foot house. It looks like they might have been able to build an 1,100-square-foot ADU in the backyard, but I don’t think many people want to do that. Becoming a part-time developer can take a lot of time, and things can go very wrong.
Maybe they made a great choice. I don’t know what’s going to happen with the other house, and I thought about that quite a bit. Is it a teardown now because the house next door is 5,000 square feet? It seems disproportionate to the neighborhood. There’s something messed up in the dynamics.
It feels like incremental development either isn’t allowed or isn’t thought of as an option. Maybe that’s a problem with boomers: they’re not good at thinking, “I need to move to a different house. I’ll renovate the kitchen at great expense, but I’m not going to build a big ADU in the backyard.”
I had two immediate reactions. The first was aligned a little bit, Andrew, with your less emotional side. This is representative of an affluent baby boomer mindset, but I don’t think it’s the dominant experience of baby boomers. Also, the guy was 64, which I’m going to look over at Richard and say is still young.
Let me say this in a nice way. I know a lot of people who have entered retirement with a lot of vigor, plans, and dreams, and then all of a sudden a switch flips. You break your leg. You suffer a heart attack. You meet something that changes your life. The people in this story have not come to grips with that or experienced it yet. Hopefully they won’t for decades, but at some point everybody does.
They’re young baby boomers, and this may describe a very minority experience: young, vigorous, highly affluent baby boomers who have reached a point in life where they can fulfill every dream they had, travel the world, buy a big house, and host Christmas. I think it’s wrong to overrepresent that.
The other question I struggled with is whether downsizing is really normal throughout history or whether it’s an expectation we created. I think of the World War II generation. Maybe I’m just speaking from my own experience, but the people I knew from that generation tended to live in more modest homes to begin with. There was no downsizing because they were already living modestly.
My grandparents lived in a very modest home. My wife’s grandparents lived in very modest homes. Baby boomers may have had a different expectation because their baseline was higher than what prior generations experienced. Was there an expectation of downsizing that wasn’t historically based, but was simply culturally anticipated, so now we’re measuring this generation against something we thought might happen someday? Andrew, thoughts?
You said a couple of things there. The article mentions one client who downsized and struggled to fit an art collection into his new home. We’re not talking about normal people at that point.
But to your point about different expectations and how people think, I do think that’s real. There’s a line in the article that couples see their late-in-life residences as their dream homes, a celebration of their lives and achievements and a chance to invest in themselves.
As a Christian, this is something I’ve wrestled with when talking with my parents and their peers in the church community. My experience is that boomers really idolize houses and cars. You’ll see people make what I consider unreasonable sacrifices to have bigger houses and nicer cars, which reflects an underlying value: they see their identity as caught up in those things and believe it’s very important to how they feel about themselves and how other people will feel about them.
That’s just my lived experience. We’re talking about millions and millions of people, so this doesn’t describe everyone, but it’s a common pattern I’ve encountered. It’s not surprising that it came up in the article, and if people feel that way, of course they don’t want to downsize. The article says downsizing can feel almost like a sentence, as though you’ve demoted yourself to a lower social class.
Or worse. I don’t know exactly what “a sentence” means, but I read that as acquiescing to age.
That too. You’re giving up.
Besides interviewing some people who had gone through this, the article interviewed a lot of realtors. Realtors do a very good job of promoting their craft: everybody is upsizing, everybody is buying, and you shouldn’t miss out.
Richard, from a builder’s standpoint, has your experience been different? Would you interpret this differently than some of the realtors who suggested it’s a widespread phenomenon?
The article says boomers were supposed to downsize. Whether you think you’re supposed to upsize or supposed to downsize, that’s a problem with human behavior. People are going to do what they’re going to do, so maybe the expectation of downsizing was unrealistic.
If someone is a boomer and grew up in a 3,000-square-foot house with a bunch of kids, are they going to move into an 800-square-foot ADU in the backyard? Probably not.
My dad traveled the world because he was in the Foreign Service, so it wasn’t fancy art, but it was stuff from all over the world. It’s nice to keep that, and it’s hard to fit into a smaller place. Another article referenced here was titled “Why Older Millennials Are Aggressively Downsizing Their Lives Before They Even Hit 50.” The next generation may have to start early. If you wait until you’re 70 and you have the art collection, it’s not going to be easy at all.
The expectation of downsizing may be unrealistic. If someone downsizes a little bit or makes their house more flexible so the kids or in-home care can stay there, that’s a pretty neat thing. It creates variety in how people use their housing.
Here’s something I struggled with, or at least a thread I think is worthy of discussion: how housing as wealth shapes the way we think about spending decisions and lifestyle decisions.
Baby boomers grew up during a period when housing values appreciated faster than inflation, and that accelerated over the last 25 years. Their experience has been that they buy a house and it gains wealth much faster than a stock account, savings, a pension, or a 401(k). It has been a great investment.
That hasn’t necessarily been the case for other generations. I’m a bit behind the typical boomer, and the house I built went through the appreciation of the 1990s, the rapid acceleration of the early 2000s, a huge crash, and then more volatility.
I wonder how much the boomer concept of what a house should be is based on a different set of experiences than other generations have had. Richard, you’re nodding. Do you want to take that one first?
There’s a lot going on there. If they had stayed in the 2,000-square-foot house and added a 1,000-square-foot ADU, their banker, realtor, and stock adviser might not have been happy. You don’t know how well that will be valued. They might have been better off tearing the house down and building a McMansion.
The numbers can work nicely for ADUs, but it’s a different thing and people don’t really know how they’ll be assessed. It becomes a pretty big risk. It’s a lot to ask someone to do something quirky with a house when there are McMansions around them.
That quirkiness is something I’ve seen a lot in older cities and older properties. You’ll see a home that’s really well suited to the people who live there, and objectively you’d say it’s a very nice home, but it struggles to sell because it’s too tailored to them. You can’t find the buyer who needs that exact same space.
It’s too bad, because it goes to a point Chuck has made many times: when our houses are critical financial assets, personalizing them to fit ourselves becomes a financial risk we can’t afford to take. Is that really the world we want to live in? I’ve experienced that firsthand.
I think about when Michael Jordan’s house came on the market. The idea was that it would be super expensive, but they couldn’t find a buyer because anybody with that kind of money didn’t want a house customized the way Michael Jordan did. Ultimately, someone bought it almost as a museum piece and turned it into an Airbnb.
I used to do lakeshore permitting for high-end properties. I worked for cities where people from the Minneapolis–St. Paul area would buy a small cabin as a second home, scrape it off, and build a retirement home or a large lake home.
They were all building their own castle. The next person was never going to buy your castle. They were going to buy the crappy cabin next door, tear it down, and build their own vision because the price would be essentially the same. My theory was that this would ultimately devalue all of those homes.
I’m not sure we’re there yet because there’s still a market for high-end shoreline property, but I don’t know whether the return on investment is there. Richard, is that what you’re getting at? It’s a small and unusual market, and as an investment property it may not be the way you make your return.
Yes. Think about the colors people use in European kitchens. They do whatever they want and make really fun choices. Americans are reluctant to use something like orange tile because they’re told they’ll lose $10,000 when they sell the house.
It’s hard, and you can get in trouble if you do something unusual. We renovated a place beautifully and are renting it out. We put on a gorgeous deck, but people don’t care about a gorgeous deck. They want another room with a big television. It’s humbling when you find that out.
That pushes people toward being very conservative and trying to do what they’re supposed to do, which is problematic. If we have housing choices, there shouldn’t be one thing we’re supposed to do. There are these conventional stories, and you can lose money if you depart from them. Or maybe your kids won’t visit because the place is too quirky and they’d rather stay at a hotel.
Andrew, I feel like there is a majority baby boomer story that is not this one. I’m going to push you a little because you talked about your experience with people in your congregation, and I respect that. I shake my fist at my parish council, which insists on building big parking lots around the church and tearing down the neighborhood to make it happen.
We struggle for priests, yet we started a new parish outside town so people who live in big homes out of town can have a parish closer to them that they can drive to, with a big parking lot, instead of coming into town.
I do think there’s another experience, and I watch it happen with my parents, who are in their mid-70s and solidly part of the baby boom generation. There’s a recognition that they can’t maintain a 5,000-square-foot house or take care of that property.
For all but the very affluent, this type of housing becomes a burden. I see a lot of people get stuck because they expected a high payout but didn’t anticipate the high transition cost of whatever they want to move into.
At least in my community, there’s a dearth of housing that would feel dignified for people of that age. You can move from a 2,500-square-foot split-entry suburban home to something else, but that something else is likely to be assisted living or an apartment complex. It’s not going to be a house in a neighborhood where you envision yourself living among other people.
I have some empathy for that. We can say these are self-created problems that boomers created through their housing choices, but the article doesn’t represent what I see as the dominant problem many aging people face when they’re forced to make housing choices in today’s market. Do you have thoughts on that?
I see a lot of people struggling with hard choices. That’s the conversation I overhear both from boomers themselves and from millennials talking about what their parents, aunts, uncles, and other relatives are going through.
It goes back to something you said earlier. A lot of people reach a certain age with a lot of vigor. They think of a new home as a celebration of life and achievement and a chance to invest in themselves. The thing is, you don’t know how long that will last.
My parents moved in their late 50s from a two-story house to a one-story house of a similar size. They had watched other people end up in houses they couldn’t maintain, and they didn’t want that to happen to them. They’re not having trouble with stairs yet, and they’ve been in their “new” house for more than 10 years, but they were thinking ahead.
Other people make different choices, and it doesn’t necessarily matter how old they are because you don’t know when you’re going to have problems. My grandparents moved in their early 70s from Dallas, where they had lived forever, to a golf-course community two hours away. They were excited, but the whole family wondered what they were doing because they were leaving a manageable house near family for a place far away from support.
I don’t think they ultimately regretted it. They had always wanted a house in the woods, and they did it late in life. But people do get stuck. They make decisions that seem like a small risk at the time, and then things don’t work out.
It’s very human. Nobody is excited about getting older and facing new limitations. No one looks forward to their body beginning to struggle, so it’s natural to tell yourself, “I’m not going to have that problem. I’ll still be driving when I’m 90, and I’ll be fine.” If it turns out you aren’t fine, and decisions you made two years earlier are hurting you now, you rolled the dice and lost. That hurts, but I can’t say I would never roll those same dice. It’s human to want the experiences you’ve always wanted, even if they seem a little late in coming.
Richard, the article talks about boomer families welcoming their kids back into spare bedrooms, building backyard cottages, and having their children and grandchildren live nearby.
My experience has been the opposite, and I feel like the world would be better if we could accelerate the opposite: the kids own or run the main house, and the parents live in the backyard cottage or use a spare bedroom or two. I’ve experienced that myself and seen it work well in a number of places.
I don’t know whether you’ve seen one arrangement work better than the other, but there seems to be a natural evolution where the parents don’t need the huge place anymore, but they would like to be close and everyone would like them nearby. What has your experience been?
There could be a Midwest-versus-East-Coast difference in expectations. Some good friends of my mom moved to King William County, about 40 minutes outside Richmond. They had a beautiful old house, fixed up an old structure as an ADU, put in a beautiful swimming pool, and planted beautiful trees.
For 20 years, they hoped their children and grandchildren would visit much more, and eventually they moved away. I’m encouraged to hear your story because the opposite can be sad. The big house might work well for two or three years, but if the kids get busy, you may not see them much.
Then a lot of parents move out of that house and may not sell it for a big gain because it’s quirky. The article mentions a professional-grade meat cutter for prosciutto. That may not feel right to the next buyer. Maybe the house next door would have done better with a large ADU instead.
There’s something unusual happening in Richmond. Kevin Vonck, our director of planning and development review, is working on a code refresh. We already allow ADUs by right, but he’s suggesting that you could build an ADU up to 1,000 square feet even if it’s larger than the original house. If you have an 800-square-foot house, you could build a 1,000-square-foot ADU.
You could do the East Coast version where you move into the bigger house and use the smaller one for your kids or for something else later. More flexibility helps people avoid getting stuck with something that’s too small or too big.
Before we switch into the Downzone, I’m going to give Andrew and Richard both a chance for final thoughts on the article. Is there anything we haven’t covered that you want to make sure we discuss?
Maybe not the article itself, but the last thing you were discussing. I think multigenerational housing is an underexplored topic. We talk about it in a hierarchical way: who gets the big house and who gets the little house? Is the ADU actually the big house in some cases? There’s an assumption that bigger is better and smaller is worse.
We inherited an image of aging grandparents needing a modest place to live out their last few years. But we’re living longer and staying healthier longer, which is wonderful. People may not be excited to embrace decline before they have to, so they want to keep the bigger house longer.
We get hung up on who gets the big unit and who gets the small one. I think there’s an opportunity for new housing types. What if people lived around a courtyard with six bedrooms and two kitchens, shared by two generations? That is starting to happen, especially on the West Coast, where new multigenerational housing doesn’t look like a big house and a small house or a good house and a bad house. It’s more of a shared communal arrangement that puts everyone on more equal footing.
You used the word “dignified” earlier, Chuck. For parents, anyone who lives in the backyard knows they live in the backyard. That form creates a certain implication. A parent might feel they’re accepting their decline, while a child living there might feel they’re accepting a failure to launch.
There’s a lot of opportunity to arrange space differently so people can live a multigenerational life that feels better than simply putting someone in a backyard cottage. I love backyard cottages and think we should have many more of them, but there are more options on the table.
It’s such an interesting cultural place we’ve gotten ourselves to. Richard, some last thoughts before we go to the Downzone?
I appreciate that, Andrew. We’re ambivalent about multigenerational housing. In many other cultures, it’s admired and considered a positive thing.
The idea now is that your parents have Social Security and should have enough money to take care of themselves when they’re older. You don’t want them moving in, and you don’t want to move in with them. That’s seen as low status or a bad thing.
In that sense, the article presents something positive. They moved into a bigger house and want their kids there as much as possible. What they do in five years may be different. They can change things. They could add an ADU and have someone stay there.
I’m bothered that the article feels static. It presents an either-or choice: either you’re terrified of the future and need to downsize into a tiny home because things are going to go bad, or you’re doing well and will only give up your upsized house when you’re dead. That sells media, but it isn’t where most people are.
My mother lives in a neighborhood in Northern Virginia, an expensive area where many houses haven’t changed much. There are 1,800-square-foot houses without fancy additions. People stay in them and make minor, incremental changes. That isn’t as interesting a story as Grandma moving from a 4,000-square-foot house into a small ADU and everything working out, or a wealthy family having the kids hang out in a playroom.
Baby boomers have been a massive force reshaping everything throughout my life. I first recognized it when Harley-Davidson’s stock went through the roof as they reached their 50s. Now the company has struggled as they’ve reached their 70s and are no longer trying to relive that era of their youth.
I had two uncles who bought Harleys. One got in a bad crash and probably regrets it now, but they lived that dream.
When we talk about housing, I always think that if millennials can hold on until their 50s, there will be a lot of homes available and they’ll be priced pretty reasonably because there will be a glut in the market at some point. I don’t think that’s the factor driving housing today, but it is a reality that things will shift and time will go on.
It’s interesting to have a boom, a bubble that moves through life and shapes everything. Millennials sometimes don’t appreciate that they’re also a boom, an echo of the baby boom, and they live in that wake. My generation, Gen X, has learned to surf it a little bit, or maybe just get beaten up by the waves.
I’ve given myself the last word. Let’s shift to the Downzone. The Downzone is our own quirky little thing where we ask our guests to talk about one thing going on in their life or in pop culture, something they’ve been reading, watching, or taking in.
I’ll start. I’m in the final three or four weeks of putting together the manuscript for the next Strong Towns book, and that usually forces me not to go deep into anything else that will rob me of thinking capacity.
Over the last week or so, I listened to a book called Regime Change: Inside the Imperial Presidency of Donald Trump. Bob Woodward used to write these books about every president, and going back to George W. Bush, the Obama administration, and the first Trump administration, I found them helpful in a balanced-journalism kind of way.
It’s not current-events reporting, but it’s very current reporting, which puts a different spin on it. This book is in the same vein. It wasn’t written by Woodward, but I thought the reporting was good. As much as it can be a balanced take on something that happened recently, it made a strong attempt to explain what’s going on and put the reader in the room for some of the events that have been in the news. I got a lot out of it.
Andrew, do you have a Downzone to share this week?
I want to spotlight a newsletter I really enjoy called Kids Over Cars. The author, Darren Thacker, is a former U.S. Department of Transportation staffer. He and his family have adopted a nomadic life, traveling around the world and telling short stories about playgrounds, waterfronts, museums, grocery stores, and all the places they find that are fun and welcoming to their two young children.
It’s encouraging. It shows how much fun children can have when they’re able to roam freely and how much joy that can bring to the people around them. Darren Thacker’s Kids Over Cars is highly recommended for anyone who likes seeing kids have a good time.
Before we get Richard’s Downzone, I forgot to mention at the top that you have a similar Substack. What’s the name of it so people can follow you?
Free Range City. You can find it online at Free Range dot City. Darren is a kindred spirit. I don’t really know him personally, but we’ve chatted on Substack once or twice, so it’s not surprising that I enjoy his work.
Richard, do you have a Downzone to share?
I love architecture books, so this isn’t down. Well, it is Downzone because they’re really pleasurable for me.
Last year, episode 42 of Building Culture discussed The North Atlantic Cities by Charles Duff. It’s a fun read about architecture, with many literary references that help explain why people live in certain kinds of houses.
There’s also fascinating economic history about Manhattan being crowded by shipping coming across the ocean. Luxury apartments were being used to store goods, and suburbanization followed as people left Manhattan because there was no space. It’s a lovely book. Duff sees the beauty in where people live, how they live, and the housing decisions they make.
That’s Richard Rumrill. He is part of Strong Towns RVA and a historic-property renovator in Richmond, Virginia. Andrew Burleson is our board chair. Thank you both for being here today.
I want to thank everybody for listening. If you’re a baby boomer, we love you. We’re glad you’re here and part of our conversation. If you’re a millennial, we love you too. Gen X doesn’t need affirmation, so we’re good. To all the young Gen Zers, I’m excited about the future you’re going to bring.
We’re happy you’re here and part of our conversation. Keep doing what you can to build a strong town, and we’ll talk to you next time. Take care.
This episode was produced by Strong Towns, a nonprofit movement for building financially resilient communities. If what you heard today matters to you, deepen your connection by becoming a Strong Towns member at strongtowns.org/membership.