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Today I have for you a fascinating conversation with Jill Filipovic, author of the new book “OK Boomer, Let's Talk: How My Generation Got Left Behind,” but first: Like most posts, my interview with Jill is free to all. But if you want to support The.Ink’s work, consider subscribing. Your support is what makes my conversations with fascinating people like Jill possible, paying for the research and editing support, transcription, and all the other things it takes. Subscribers are also able to join weekly video conversations with me that have been convivial, civil, thought-provoking — a balm in these times.

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For many of you, this week begins the school year. And it is sure to be the strangest school year ever.

Some parents will walk their little ones to school but be barred from entering the building. Others will patiently supervise first-graders doing math over Zoom, hovering on the outskirts of a webcam frame. Still others will drive their young around town, furtively looking for free, unguarded Wi-Fi.

This year, as much as any year, we are reminded that parents will do anything for their children. But when it comes to the workings of contemporary America, we also know that the relations of the generations are marked not only by love but also by conflict, resentment, and a struggle for power.

That child you are walking to school — or that parent helping you with math — isn’t just a member of your family. They also belong to an age cohort that today or one day, if history is any guide, will do battle with yours — over whether it’s more important to shore up Social Security or forgive student debt, over whether capitalism needs to be tweaked or upended, over whether we need banking reform or more personal responsibility to resist the temptation of avocado toast.

America today is, as I’ve said, in a cold civil war, in which various groups feel pitted against an Other. And when it comes to the fault line of age, it is an intimate Other. We are living through a battle for influence and recognition that pits parents against children, aunts against nephews. And I know firsthand from my reporting that, for all the love that traverses these generational lines, there is a great deal of rage and bitterness: young people feeling as though the society and the planet were strip-mined right before they arrived; older people feeling dissed by all the “OK boomer” talk.

For many people my age (gray but elder-millennial), it can seem like we live in a gerontocracy. To cite just one example, Bill Clinton, the Democratic nominee for president in 1992, is younger than Joe Biden, the nominee 28 years later. Yet when I and others make such arguments, it often hurts feelings and leads to accusations of “ageism.” Which reminds me of that quote that’s been doing the rounds in recent years: “When you’re accustomed to privilege, equality feels like oppression.”

All this is why I was so eager to talk with Jill Filipovic, the author of “OK Boomer, Let's Talk: How My Generation Got Left Behind.” In the book she explains how baby boomers were once, figuratively speaking, the avocado-toast-eating, narcissistic “me generation” of their time, how millennials are inventing new life paths given the circumstances they’ve been dealt, and how we can begin to have real, heartfelt conversations across generational lines about how our society broke and how to fix it. We spoke not long ago, for an event organized by the terrific Strand Book Store.

ANAND: I want to begin by reading a sentence from the beginning of the book that's very helpful in explaining what this book is. Referring to this phrase “OK Boomer” that you hear all around, you write: “‘OK Boomer’ is more than just an imperious insult; it’s frustrated Millennial shorthand for the ways the same people who created so many of our problems now pin the blame on us.” Explain.

JILL: As much as boomers are apparently profoundly insulted by people saying “OK Boomer,” well before that was a Twitter online catchphrase, there was what I call the boomer outrage-industrial complex in the book. A whole set of concerted efforts to essentially froth up generational anger — primarily at millennials.

That is certainly not new. Older generations have always looked at the young and accused them of doing it wrong. But what's different now is you have right-wing media outlets, on television and online, pinning today's ills on millennials and pinning our own problems on us.

Saying that millennials are these avocado toast-eating, hyper-PC, super-indulged, whiny babies who can't buy a house because they're spending all their money on Sunday brunch. Instead of really looking at what changed between the time the baby boomers were coming of age and were hitting adulthood that enabled them to buy homes, raise families, live in relative middle class comfort — what has shifted for millennials that we can't do that? Is it really a choice that millennials are deeply in debt, not buying homes at the same rate as baby boomers, getting married later, having fewer kids than even we say that we want?

ANAND: I want to selfishly get you to defend me in this ongoing argument that I get into. I never come out well when, on Twitter, I critique what I consider boomer overrepresentation in some sphere of American life. 

Maybe it’s about presidential politics, or Nancy Pelosi (who is actually a few years older than the oldest boomer) and Chuck Schumer — the entire political leadership. Or I talk about The New York Times’ Op-Ed roster. You're an exception on it, but there are a lot of people who have had that column for between 30 and 350 years, and I think it'd be better to just have some new blood.

Every time I get into this, I get more anger than I usually get from almost anything else I say, which is saying something — accusing me of ageism. That I am like an age Nazi, that I am doing for age what Donald Trump is doing for race. Can you help me out of this situation? Because I really don't feel the critics are right but I need your help.

JILL: I guess what I would say is that the goal is not to tell boomers that they need to be put out to pasture and go die somewhere. The request is not to remove boomers from society. The request is to share power, influence, and access and to have that be proportionate.

Boomers have dominated politics and culture ever since they came of age. Boomers are now no longer the largest generation in America — that's millennials — and yet 80 percent of the Senate is still over the age of 55. Zero percent of the Senate is under the age of 40. That wasn't true when boomers were young.

Joe Biden was 30 when he took a Senate seat. The oldest millennials are turning 40 this year. We still haven't seen a single millennial in the Senate. We're underrepresented to a degree that boomers were not when they were our age and when they were the largest adult generation.

I think it's great boomers are living longer, working longer. There are a lot of boomers with a lot of wisdom and experience to share and to impart. But when you don't have boomers sharing the stage and sharing the mic, what you get is staid politics that is not representative of what younger generations of Americans need looking forward. You get business and Op-Ed pages and magazine mastheads and nonprofits and advocacy movements that are run by people who aren’t necessarily serving or talking to the people they’re meant to be. As you say, it's not just a matter of let's get new blood; it's also a matter of, “Is this actually representative?”

ANAND: The concept of a generation is itself tricky. The way the concept of a gender or race or any kind of grouping of a very large, heterogeneous group of people is. What are the real distinguishing psychological traits of these two generations?

JILL: The thing that is made up is that we're the first generation that has invented this intergenerational conflict. Or that millennials are the first generation of people whom older folks have looked at and said, "You guys are idiots and you're changing the world for the worse." Or that boomers are the first generation of older folks whom young people have criticized for ruining our lives.

When boomers were young, they were also written off as the “me” generation by Tom Wolfe and pretty roundly lampooned as narcissists who didn't really know what they were doing. That stuff is definitely not brand new. I think what is new is that millennials are the most racially diverse adult generation in American history, in an era of incredible concentration of wealth into a small number of hands, mainly older hands and white hands.

We are the first generation that is not going to do better than our parents, that probably will not do better than our grandparents. That's true not just for the white millennials, who had long legacies of families who have tended to do pretty well. But it's also true of millennials of color for whom we have a narrative about generational rise. The reality is a Black millennial today is less likely to own their home than a Black young adult was during the civil rights movement.

ANAND: Wow.

JILL: We've seen a decline that is really contrary to some of our most deeply held national stories about progress and who's doing better than people who look like them or share their characteristics used to do. That's the part that really is new. Millennials have faced a set of challenges that young people in America have not before faced.

ANAND: Some years ago, when I was working on a project on inequality, I had this epiphany that one way to think about inequality is how different societies, or the same society at different moments in time, apportion their love for one’s own children versus everybody else's children. Of course you love your own children more, but in different societies, there are different relative amounts of love for other people's children — a greater or lesser love for the commons.

You write a sentence that made me think of that: “Much of what individual Boomers did for the benefit their own kids their generation didn’t do for society at large. Instead, they hoarded resources for themselves.” It seems like one thing to say about boomers is there was actually more love and attention and focus on their kids than in the past — and less on everybody else's kids.

JILL: I think that's absolutely right. I think on an individual level among boomers, that was not necessarily intentional. Especially among the progressive boomers who are half of their generation, who were not voting for the kinds of policies that Ronald Reagan put into place — #NotAllBoomers. But one thing that I think is pretty unique about boomers is that they were sort of the original helicopter parents.

Millennials grew up having personal relationships with coaches and teachers and parents who cared about your feelings. Boomers were often determined to do a better job at connecting on a personal level with their kids than perhaps their parents did with them. Now we're tarred as snowflakes for being emotionally mature adults who think other people's feelings matter. But that is very much a carryover from boomer parenting norms.

But at the same time that that was happening, as boomers were investing tremendous emotional resources into their children, and financial resources they had into their children, you did see this big pullback of public investment in resources. In things like higher education, in things like the social safety net. Even in things like basic infrastructure and planning for the future. That's a very different world than the one that baby boomers grew up in, where you had seen these tremendous investments that enabled boomers to go to college in record numbers.

ANAND: You write: “Millennials have broken away from what several young people I talked to characterized as ‘The Script’: Graduate from high school, go to college, get a job, get married, have kids, retire. We are marrying and having children later, and often reversing the order of those things — or forgoing one, the other, or both.” 

Clearly, all that stuff is not chosen, as you've said. It's the result of political choices made long before. But as so often happens in history, when conditions change, people invent new ways of living with that reality and find meaning in the new way of living.

Are you seeing interesting innovations of the life path that people are actually embracing? What are some of the interesting new ways of living that you're seeing among young people?

JILL: There are so many. We hear a lot about the millennial baby bust — that millennial women are having fewer children and we're having them later in life.

ANAND [thinking of his children]: Growing awareness of what it's like to have children is known to reduce the number of children people have.

JILL: Right, and being able to control the number of children you have. All these things work together in tandem. Women can go to college, or any sort of higher education, or get a job that feels meaningful. Those are incentives to have children later, to have a sense of purpose that is not just tied to the status of childbearing. 

We're seeing that millennial marriages are a lot more stable once we do get married. I suppose you would expect that if you get married at 30, you probably have a better sense of who you are, what you want, and how to manage conflict than if you get married at 17. Millennials are marrying later and marrying less often, but are also getting divorced less often when we do get married. That's a positive trajectory.

A lot of millennials have marital relationships that do not look like the traditional ones that our parents and our grandparents had. A huge number of millennials aren't getting married, but are raising children either on their own or with a partner whom they're just not married to. I think we're also seeing what your wife, Priya, has written about in her book. There are different ways of gathering and connecting when old ties of kin and family and bloodlines are no longer how we organize our lives. Well, then how do we organize them in a way that feels meaningful?

ANAND: You talk about how we should potentially adopt Swedish-like social policies that support family formation, family survival. Do you think we need policies that make it easier for people to be married or policies that make it easier for people to not be married and still do all the things in life?

JILL: Definitely both. I think we frankly need policies that recognize that human relationships are complex and that a romantic relationship is not necessarily the primary one that people will have in their lives. 

I do think we need Swedish-style benefits that accord necessary help to folks no matter what their choices are. If you look at marital rates in Sweden, among young people, they're not super high. There are a lot of women who are technically single women, but in reality, are rearing children with long-term partners. Whether or not you have a marriage certificate is not really the deciding factor of whether you can have a healthy, stable life.

In the U.S., you really see a huge difference between the outcomes of children who are raised by married parents and children who are raised by single parents. That has very, very little to do with marital status. It has almost everything to do with time and resources which we systematically take away from single parents in particular.

ANAND: Among the many waves of feminism that are invented and reinvented in every generation, what is new and interesting in millennial feminism?

JILL: So much. It's a social justice movement like any other. It is always evolving and learning and shifting. I think one thing that millennial feminists are particularly good at doing is looking at where issues intertwine. I think we're much better at realizing that issues affect different women differently and are all intertwined with each other. You might call it intersectionality, a term that was invented by a baby boomer.

If you don't have the right to decide the number and spacing of your children or whether you have children, it is very hard then to work the way you would like and be paid fairly. Abortion is an economic issue as much as it's a human-rights issue. 

Can you parent your children? Can you raise your children in safe and healthy neighborhoods that are not polluted by environmental toxins? That are not over-policed? All of these things intertwine with each other. To me, that's an exciting shift in millennial feminism that is understanding these issues are big and complex and not being afraid to grapple with them as such.

ANAND: In terms of the coming-of-age journey of millennials, how do you think the hall of mirror of likes on social media and the harassment that is so rife in the online world have shaped being young and then being ex-young?

JILL: This is going to make me sound like a boomer, but I think it's a total disaster and it's horrible for our mental health. I do worry about what happens to folks who are younger than millennials. Who have all of their youthful idiotic ideas and actions preserved forever online. One of the stats that was most shocking to me was that one in five millennials say they have no friends and no acquaintances beyond their immediate family.

We think of older folks as isolated and the lonely generation, but it really is younger ones. You're also looking at a generation that has serious mental-health issues, that often lacks health insurance, that is often in debt and often holds medical debt. Then you hand them all the technological innovations that make bullying very easy, that make harassment very easy, and that make isolation very easy.

As much as I think technology is amazing and is working for us quite well right now, there have also been a lot of really disastrous impacts. I think millennials are the canaries in the coal mine for some of the bigger problems that are waiting for us.

ANAND: It's very hard for people in any walk of life, whether they can afford it or not afford it, to actually cede power. What can average boomers do if they agree with you?

JILL: As I said earlier, boomers are an incredibly politically polarized generation. Often when we talk about boomers, including when I talk about boomers, there is a tendency to paint with too broad of a brush and indict the whole generation for the conservative half of it.

With that said, on an individual level, I would love to see boomers thinking about, How can I pull up a seat, at whatever table it is that I'm sitting at, for younger people? Not in a, This is our Youth Council and pat them on the head way that Democrats did with the DNC. But how can we actually share power, share resources, really hear what younger folks are saying, and not just write it off as youthful folly or inexperience?

Including whom you vote for. Look at how younger folks are voting. They have a much bigger stake in the future than older ones do. It's very easy for people to write off politicians like AOC, who seems to be one of the most polarizing people in America. I think it'd be worth it for boomers to listen to what she's saying and ask themselves, Why is it that young folks are demanding universal health care?

One relatively small but I think impactful thing that boomers could do is really listen to younger folks and see not just how you can incorporate their feedback, but also help move them up the chain. That is something that everyday people can do. And starting to vote for millennials would be helpful, too.

ANAND: You're calling for the rise of the boomer ally, which I think is a good idea.

JILL: Exactly.

[Anand begins to draw on questions from the audience.]

ANAND: I'd love to hear your future predictions about the Overton Window. What sort of things can we feel optimistic about and will feel like a no-brainer by 2040?

JILL: I think we can feel optimistic about so many things. Millennials are moving the needle quite a bit on issues of race and gender. Issues like the fight over trans rights we're going to see as relics, I hope, in ten or 20 years. The idea that transgender people exist and should have the same rights as everybody else to live as who they are and with dignity will, I hope, be something that we look back on as obvious and feel ashamed about what we're doing now.

I hope when we look back on the Black Lives Matter movement, we're going to see it certainly through the same lens that we see the civil rights movement now, which is that everybody lays claim to it. We all agree it was a good idea. Even though right now, clearly, the American right does not think that. I do think when you look at who's been protesting on the streets this summer, it is overwhelmingly people under the age of 40. I think if those are the kids carrying the future, I feel good about where we're going on gender and race.

ANAND: How do you see neoliberal capitalism fitting into all of this, specifically in millennials’ cultural attitudes as compared to boomers? Maybe you can answer that question by way of the big socialism question.

JILL: I think that's a cornerstone of this whole book. Neoliberal capitalism has failed millennials. I think that's clear in how we vote and the fact that we are a generation that doesn't see socialism as scary. Most of us grew up at the tail end of the Cold War or after the war had ended. We didn't grow up with that looming sense of fear of We're going to get nuked and so let's hide under our desks because that's going to shield you from a nuclear apocalypse.

We can see that a young person in Finland is not going to have five- or six-figure- student-loan debt unless they went to school in the U.S. We can see that a mother in Sweden gets nine months of paid leave to take care of a new child and that a father in Sweden gets the same thing. The word you may put on that is socialism, which was such a boogeyman for our parents' whole lives. But for us it's sort of defanged. To us it describes a system that, frankly, looks a lot better. I think that the conditions of American capitalism and where it has left millennials absolutely shape our generational shift toward the left, and for many of us toward socialism. I think a lot of boomers look at that and they find that scary, and I understand that. 

ANAND: I want to read you this from the online comments — it’s a sentiment that is not rare in this discussion. “It sounds to me as if you haven't had deep, heartfelt conversations with enough boomers to understand the struggles and challenges we faced as young adults. We grew up protesting the Vietnam War, racial injustice, sexual assault, inequality and more. Many of us are not traditionalists. We grew up with high ideals with a desire to change the world — peace and love. The boomers you describe sound more 50s-driven. We did the women's movement much more.” What are your thoughts?

JILL: I hear that a lot. Yes, absolutely. It is not the case that all boomers are right-wing reactionaries. It is the reality that, first of all, boomers were not the founders of the civil rights movement or the feminist movement or even the antiwar movement, although they certainly were foot soldiers in a lot of those movements. But that was a pretty small number of people. This is, again, something that I think the whole country now lays claim to. But those movements were all really unpopular in their time.

Part of my hope with this book is that the boomers who were doing the protesting, who do lay claim to those movements today, are the ones who are going to be receptive to this. They're not the folks who are voting for Donald Trump. The goal is to talk about, How can those folks who've been doing work on issues that millennials also care about help us to pick up the torch? How can we collaborate? How can we work in tandem to create a future that millennials and younger folks need?

ANAND: Looking at the comments on the sidebar as we speak, there are hurt feelings. There's all kinds of exciting things going on there. But I think this is all very important. It's what books are for. I congratulate you for starting that dialogue with this book. With the pained chat in mind, what will it take to have the kind of intergenerational dialogue that might actually push things forward on this issue?

JILL: I think it's going to take a little turning down of the temperature and a little humility on both sides. That's what I tried to do with the book. There are a lot of boomers who’ve been working on the issues that we care about for most of their adult lives. People like Bryan Stevenson are a baby boomer. Loretta Ross, she's a baby boomer. Kimberlé Crenshaw is a baby boomer. Feminist writer Rebecca Solnit is a baby boomer. RuPaul is a baby boomer.

There's a ton of boomers who have been doing this great work for a long time, from whom millennials have a tremendous amount to learn. I think us coming into this discussion being a little less overly simplistic about who boomers are would certainly be useful in fostering discussion.

Then from boomers, I would love to see a little more open-mindedness about the fact that, when you were young, people accused you of doing it wrong, too. 

Millennials who are picking up the torch on issues like feminism, on issues like racial justice, on issues like LGBT rights — we’re sometimes going to frame these issues differently, we're going to come at them differently. That's because you guys moved the needle forward. We're not fighting the same fight that we were fighting in the ’60s and not in the same way. Allowing millennials the space to take up positions of power and to have more influence over where these movements are headed, what they focus on, how American politics looks going forward is really crucial.

Jill Filipovic is a journalist based in New York and author of "The H-Spot: The Feminist Pursuit of Happiness,” and, most recently, "OK Boomer, Let's Talk: How My Generation Got Left Behind,"

This interview was edited and condensed for clarity. 

Special thanks to Strand Books, where you can find “OK Boomer, Let's Talk: How My Generation Got Left Behind” and other titles.

What you’re saying

Some highlights from your recent comments at The.Ink

“America is on fire. To save (and rebuild) her we must first extinguish the flames...In 2024, if the fire is out or at least contained, the rebuilding can begin in earnest.”

• An American Gypsy, August 28, on “We are in a cold civil war” 

“Biden's not the issue. We could win the popular vote by 6 million — and Trump could still get reelected. The issue is the systemic flaw in our election process known as the Electoral College...Biden is pressing as hard as he can on the brakes — but the laws of physics are immutable — and it's very possible we've played with them — and defied them — for just too long.”

- Dan Munro, August 28, on “We are in a cold civil war” 

“Let's stop talking about Trump as a failed president and talk about the madness that he is sanitizing: unemployed and too many dead people, climate change, separated families, military bounties and the ridiculous inequality in this country. Honestly, the real work begins after this election — even if Biden wins, we must hold him accountable.”

- JR, August 28, on “We are in a cold civil war” 

“I am so glad Varshini had the opportunity to influence the Biden environmental plan...This is one of my expectations for a Biden-Harris administration. We need to hold them accountable to create a collaborative approach to governance that will be inclusive, that will serve all Americans, and lead to accomplishing the things we need.” 

- Nick Santilli, September 1, on “To solve everything, solve climate”

“I, too, hope that once we have practiced our privilege to vote that we will sit down at a breaking of bread and a willingness to find solutions. There will be a lot of cleaning up to do in aisle 1600.”

- Catherine Yoshimura, September 5, on “Joe Biden is the water, not the tide”

See you soon!

Anand

Photo: Getty Images / CSA-Images