Discourse won't Save the Boomers (but let's try anyways)

Is it really possible "red-pill" your parents?

So it turns out that my last letter was built on a faulty premise. Perhaps a follow-up is in order?

In my last Substack entry, I painted a picture of a dissident community preoccupied with helping young folks and building a future apart from the past. This would be ideal, but it’s far from reality. Even when it comes to generational problems, it is plain to see that most of us aren’t so much concerned about mentoring the young as complaining about the old. Truth be told, when it comes to the energy and time spent on discourse between age cohorts, there is one, and only one, elephant in the room: the “Boomer Question”.

And what is the “Boomer Question” you ask? Where do I begin when discussing the many issues surrounding the aging members of “Baby-Boom” generation? The Boomer generation is the runaway train carrying our civilization mindlessly towards a future that cannot possibly exist. The Boomer generation is the nuclear reactor, once so productive, now on the verge of meltdown if not turned from its trajectory. In turn, the “Boomer Question” is a primary obstacle for all those (left or right) who think that our society needs radical change. Given that generation’s size, power, and comfortable disposition towards the status quo, how can anything change without their approval? How can they be convinced, or dissuaded, from the course that have chosen for our society? Any large-scale political change hinges on this question, and so the “Boomer Question” is eternally lurking in the background of our discourse.

In some sense the “Boomer Question” is the opposite of the “Zoomer Question”, just as the “Boomer” generation’s experience (now culminating in retirement) is the photo inversion of the Zoomer generation’s lived reality (now languishing in early adulthood). Whereas the Zoomers were born to a degenerating world of declining institutions, non-existent moral consensus, and a governance system want to regard its population as obstacles to a future that might not need humans, the Boomers were the golden children of America, the generation that all history built towards and wherein culture itself seemed to climax. Whereas the Zoomer’s are perennially plagued by pessimism, there is a sort of blithe innocence to their Boomer counterparts even in their old age. Perhaps its strange for seniors to be more idealistic than those in the prime of life? But maybe not. After all, was there ever an American generation more optimistic than the baby-Boomers?

The Boomers were the generation born to an America of possibility. As children, the generation repeated the benefits of the West’s right-ward shift in the 1950s (rare!), before commencing its undoing in the 60s. They then went on to exchange their idealism for hedonism in the 70s, and then their hedonism for careerism in the 80s, before sliding into a comfortable middle-aged affluence built on a real-estate bubble that could never last. It was a generational path that worked, at least for them, at least for a time. But could it last? Could it work for their children? Could it work for their grandchildren? Who knew? Among all American generations the Boomers were king, and as the king is want to say Après moi, le déluge.

From this vantage point, a neophyte might think the “Boomer question” to be a question of generational envy. Yet I don’t think this is the case. Some nostalgic taste in music and movies aside, few Millennials (or Zoomers) want to follow the path the Boomers blazed. This is not a conflict where a foolish youth wishes to return to a libertine lifestyle, sternly prohibited by responsible elders, all-too aware of its dangers. In fact, the situation seems quite the reverse with a younger generation more disillusioned than the old. With realist Millennials and Zoomers trying to pull their Boomer predecessors kicking and screaming into the dessert of the 21st century to answer the hard questions of modernity. Neither side of the conflict, young or old, thought they would be in this position.

Boomers see themselves as the last revolutionary generation. Or at least the last successful revolutionary generation. Not only did they break all of the rules of society before them, they showed that the post-1969 world could work. They were able to navigate through the changed social landscape. They got jobs, started families, got reasonably wealthy, made good, all the while never suspecting that the Gods of the Copy Book Headings who they rejected in principle (and followed only in pantomime), might someday return and demand something more than a hand-waving acknowledgement of “common sense”. But return the old gods did, and the Boomers (somehow strangely still in power) can’t even understand the nature of the problem that confronts them. The world they thought they had secured is suddenly disintegrating at its apex.

It would seem that this frustration with the Boomer’s mentality defines Millennial and Zoomer politics, just as the specifics of that frustration define their left-right split. It’s obvious to most reasonable young people that the promise of the 1960s has failed. The only remaining question concerns the cause of that failure. Did the 1960s go too far? Or did they not go too far enough? It’s obvious we didn’t achieve John Lennon’s Imagine, it’s obvious things are getting a lot LESS like John Lennon’s Imagine, year after year. So what good did our sacred civil-rights revolution accomplish? Do we need to turn back, or double down?

It’s an old story indeed, right-wing recusants against left-wing puritans, this time with an ironical inversion of dialectic roles: a left-wing that wants to “stay the course” and a right-wing that wants to veer off radically towards a different vision.

This divergent relationship to the Boomer generation’s grand narrative also explains the left’s advantage when appealing to power in the culture war. The Boomers, at the top of our society, are still children of the 1960s. Even if they didn’t directly experience it, they lived and breathed its promises across the 70s, 80s, and 90s. Now they have a chance to put those beliefs into practice. Is there even a question which side they will pick? As strangely aggressive as the new left appears, Boomers will naturally chose the starry-eyed Utopian dreamers, especially if the alternative are scary traditionalists who want to raze their entire project to the ground.

And for this reason, the “Boomer Question” couldn’t be more clear. They hold the reigns of power. They carry all of the keys. They guard all of the doors. And, in the short-term at least, any reach for power is going to have to go through them. The Boomers need to hear a new message. They need to think different. But can they? Are they even ready to listen? Will they ever be?

Certainly convincing anyone of anything is never easy. And Boomers possess that special trifecta of traits that makes them particularly hard to persuade: old, rich, and over-confident. Yet, in spite of this for all their other ontological limitations, the Boomers have a singular type of sincerity. Deluded as they tend to be, Boomers believe the things they say, and they are less tainted by the culture of ironic detachment that so infested the later generations of the 20th century.

Ultimately, any attempt to use discourse to reach members of the Boomer generation is likely to fail. But if one wanted to try, the best bet would be to lean into this instinct of sincerity and sincere optimism so distinctly felt by America’s last revolutionaries.

Perhaps you might start with Boomers who care about something you care about. Start with older folks who share your values or a community of concern. Then use this as a starting point. Examine soberly (at least as soberly as possible) how future events might help or hinder your shared goals. Remember Conquest’s First Law? With enough patience and understanding, progress can be made.

Of course your millage may vary depending on the circumstances. It’s hard to really know what is possible. Perhaps one can impart a basic understanding of a dissident worldview? Perhaps one can encourage apostasy from the mindless secular liberal mainstream? Perhaps a complete red-pilling? It’s hard to say, but before this gets too abstract, I want to narrow the focus of this essay down to one particular type of Boomer that’s probably at the forefront of most readers’ imaginations.

How do I red-pill my Parents?

Yes, we are starting with one of the most common questions asked to my blog over the half a decade of its existence. To be honest it’s probably what most of us are thinking when we think “Boomers” anyway: our parents, simultaneously the most helpful and most frustrating people in our lives. And wouldn’t you know it, they also meet our criteria for people reachable through discourse! We share values with our parents and have common concerns about the future, almost by definition! So how does one “red-pill” their parents?

Typically, the sage advice (and my own advice for anyone who asks me this question) is “don't try”.  Attempting to argue politics with relatives, parents in particular, is a quixotic endeavor.

Form the outset, the problem is basic. In addition to the reality that it is hard to convince anyone of anything, parents in particular are inclined to never take their children's political opinions too seriously. I know this might be hard for you 20-somethings out there, but your parents never really got over those thousand times they had to change your diaper when you were a toddler. Speaking as a parent, I can confirm. I love my son dearly, but part of me is always going see him as a baby. And when that day comes for him to don a professor cap and lecture me on how my political ideology is “crap” because of my failure to properly understand Heidegger, I am not sure I will be able to completely purge the image of him pouring his pasta bowl over his head and yelling "CHEESE!". In this light, his well-researched attempt to unsettle my understanding of politics will be a hard sell.

But wait….what is the actual point of this digression? True enough we all emotionally start with our parents as a model when we think of the older generation. But our parents aren’t the ultimate target. They aren’t the ones in power, they aren’t holing any reigns. And, if convincing parents is particularly difficult, why are we complicating the matter and making the task harder than it needs to be?

Yes, granted this approach does complicate the picture. But the example of parent-child interaction is key. Boomers see all of the subsequent generations as children. It probably doesn’t hurt that many in those subsequent generations are literally the Boomer’s children, but there is also a more general dynamic playing out. The Boomers are eternal children themselves. Their focus on caring and innocence was central to their revolution, and this has colored how they see humanity and politics. In the eyes of their predecessors, can the progeny of the flower child generation be anything but children themselves? Regardless of how experienced we are, we will always be children when conducting discourse with Boomers.

But given this limitation, given how disinclined people are to take their children seriously (politically speaking), how can we break through?

Well, it turns out that parents, and older peers, do sometimes learn from the children, but only in very particular ways. Here, I might start with the classic proverb:

"From the mouth of babes comes wisdom".

which is widely acknowledged as true even though the actual quote is:

"Out of the mouth of babes and sucklings thou hast ordained strength",

and the quote is from the book of Psalms not Proverbs. But either way, the point is taken. You can learn from the young. Those little bundles of joy are an educational experiences, and not just in changing diapers. But, if someone is receiving wisdom from a child, it would probably help if that knowledge had a child-like simplicity.

After all, what type of insight would you accept from a baby? Something innocent, or very basic at least. You probably aren't going to learn theory from a toddler, but you might listen when she reminds you of obvious facts right under your nose, too obvious for your worldly adult brain. The sky is blue, men are men, the emperor has no clothes. These are basic truths. Children know them and say them, and only adults are confused enough, educated enough, to want to deny them. And these basic insights are even more poignant when (Trebek-style) they are phrased in the form of a question.

People, regardless of how much they love you, aren't amenable to being corrected. But questions, or very basic observations, impose themselves. After all, parents have been answering your questions, and contextualizing your observations for decades. It's part of the job description. Answering your questions used to be easy, now it’s harder and requires some uncomfortable self-examination. But can a parent really dismiss an earnest question outright? Wanting to take a child’s curiosity seriously is their natural role. Refusing to do so is almost a dereliction of duty.

And this nature should be embraced by most people who want to make an impact on the older generation. Most wisdom traveling from the young to the old, from the innocent to the experienced, from the low to the high, is best when it follows the natural conduit established by generation of humans. Deep, nuanced, and theoretical wisdom flows downward towards the young. Sincere, experiential, and inquisitive insight flows upwards towards the old.

So this being the case, let’s build something more specific. Imagining we were planning our a discourse with a Boomer peer (possibly a Boomer parent) how would we structure a group of questions and basic observations? What would such a discourse even look like? Here, I provide a quick analysis for each of the two main Boomer cohorts: the Red-State Boomer and the Blue-State Boomer.

Questions for the Red-State Boomer

Starting with the easiest of the two options, the Red-State Boomers have just one (big thing) to get over: the American conservative movement and the mythology of the American founding (one actual thing!). Red state Boomers also have the distinction of being prominent losers on the American political scene. True, many were in denial about this fact, until very recently. But the Red-State Boomers are slowly waking up to the century-long American practical joke that has them as the butt. Cruel reality? Perhaps. But it makes them more likely to listen to a different point of view.

At any rate, the Red-State Boomers are asking themselves questions right now. And some particular questions, delivered by younger voices might point them towards greater truths. Perhaps something like the following set of questions?

1. “Why should we care about the constitution when so few people in power recognize that it has a consistent and binding meaning?”

2. “If the constitution doesn't bind the government, like the founders intended, what good does it actually have? Would the founders themselves have valued a barrier to abuse that doesn’t actually constraint power?”

3. “If the American founding relied on fundamental religious values, shouldn't we be more loyal to those values than the form of the government itself?”

4. “Do you think our government actively detracts from our values. If it detracts from those values today, how long has it been doing this?”

5. “How is it possible to re-establish our foundational values when the government has been undermining them for a hundred years?”

6. “If our religious principles come from a society that wasn’t democratic, liberal, or constitutional, doesn't that mean that a non-Democratic or non-constitutional society might be better at maintaining these values?”

Once more, we are just trying to pop the conservatism thought bubble. This is a pretty standard line of questions, and phrased appropriately they should work to spark some dangerous thinking. Red-pilling the middle American normie-con is basically down to a script at this stage. And probably very few people (familiar with this side of the internet) are not familiar with these types of questions. However, to take it a step further, we need to mark a common pitfall.

Often, after a tricky conversations about politics, Boomers defer to confusion. They acknowledge the points in theory but then to never follow-through and drift back into the comfortable marinade of the conservative outrage cycle so exploited by National Review and Fox News. As such, these conversations, even with the same person, can have a “Ground Hogs Day” feeling of constant repetition. More often than not, it’s less about convincing these people than getting the message to stick.

Here, I think two words need to foremost in one’s minds when trying to break this cycle: “priority” and “imperative”. These notions should be the frame for all conversations with Red-State Boomers, even if implicitly. First, our problem is a problem of priorities. The Boomers have their priorities backwards. They think about politics when they should be thinking about religion, they consider the next decade when they should be thinking about the next century, they ask themselves how to defend America and the constitution when they should be thinking about God and their posterity. Always return to the question: Which things are the most valuable things?

Keep on pressing the question. They know the answers even if they sometimes pretend that they don’t. Is what that Republican political candidate saying really important? Is this the thing that is really going to make a difference? Should we be asking about how to help preserve the constitution at this late stage, or are there more important concerns surrounding faith, community, and civilization? And if this <insert politician cause of the month> isn’t the thing that is going to make a difference, what are the things that will make a difference? Our time is short.

As always, when speaking with elders be sure to provide hope and patience. For the Boomer in question, you are removing a layer of security and trust they thought was there. This needs to be done gently. Despair helps nobody, and they need to be aware that there are other young people who care about standing up for the things which are truly import. This can be a long process, but it does occur organically.

Alright, but if that process seems too easy, maybe something more challenging?

Questions for the Blue-State Boomer

Trying to reach a progressive through discourse is a challenge. If red-pilling a Red-State boomer was breaking into a piggy bank, red-pilling the Blue-State Boomer is breaking into a bank vault with lasers, motion detectors, and a constantly updating security system.

Blue-state Boomers already think that they are the smartest homo-sapiens ever to have lived in the history of the planet, and 60 years of cultural victories hasn't helped their hubris. Furthermore Blue-State Boomers read mainstream "high-brow" publications that provide a daily dose of the most sophisticated crime-stop shipped in fresh from the Ivy leagues. There are no unguarded gates in the mind of a reasonably educated progressive baby-Boomer, and more likely than not, they will already have an opinion about your world-view before they even understand it.

But the problem goes deeper. Blue-State Boomers (unlike most past generations of Westerners) are now willing to discard previously held principles in order to persevere the impression that our current academic and media establishments are virtually infallible. For them, their political “side” is less a cadre of interests and promises (which might fail), and more a religion or god (that can only be failed). This is what gives us well-known progressive cultural phenomenon such as the "unprincipled exceptions" and the "moral parallax", where contradictions and incongruities can be folded seamlessly into the left-wing narrative without a hitch.

When disagreeing with a Blue-State Boomer expect to see plenty of burden-shifting, goal-post moving, and preening moralism at every point. Every turn in the conversation will be another opportunity for them to denounce you as evil. For what it’s worth you might question whether they are speaking in good faith, but most of the time they are. This is just how they have been taught. Very likely none of their rhetorical trickiness is willful. They don't even know they are playing that kind of game. They are simply reciting the litanies and ablutions of their priest caste.

Nevertheless, despite the difficulties, our solution to the Blue-State Boomer is fundamentally no different than before. We are talking to someone who thinks they know better than us. They can dismiss anything we argue, but if we stick to questions or basic experience-driven observations, break-through is possible. Personally, I have found rhetorical moves will only be effective with a temperament of blithe innocence. But it’s simple to approach a conversation in this spirit if you try. For example, the following observations might give even a dyed-in-wool progressive pause:

1. “I don't feel like our society is making progress. Things look a lot worse now than when I was younger.”

2. “Why does it seem that past progressive policies haven't actually made things better?”

3. “Do you really think we are going to solve this <progressive problem> by doing this <progressive policy> again?”

4. “I feel like if things keep going this way, my life (the life of my child) will be much harder and less safe.”

5. “Do you think anyone could have predicted that this <failed policy> might not work?”

6. “Why does it feel like we have tried a lot of these approaches before?”

7. “Have we considered that there might be solutions to these problems that aren’t considered progressive (or liberal)?”

Note here that these observations primarily work to manage your presentation. As someone who will be perceived as a child, your goal is avoid the image of a tantruming toddler demanding entitlements. Seek instead the image a forlorn innocent, on the verge of despair over a false vision that was promised. Think of adjectives like “tragic”, “wistful”, and “sincere”. Try to incorporate a common theme of disillusionment and searching. This present world isn’t the future the Boomer’s imagined when they first clasped eyes on that civil-rights movement. They might deny it in their rhetoric, but deep in their bones they know this is true.

Also, notice that our scope has changed  drastically. Whereas with the Red-State Boomer we were guiding them to a conclusion, for the Blue-State Boomer we are are simply introducing doubt.

The Blue-State Boomer is far down the rabbit-hole and will perceive any attempt to change their mind as an aggressive attack on their dignity. Ordinarily this would make push-back impossible. But for those progressive who have reason to care about us anyway, this defensive instinct that can be subdued behind the veil of inquisitive candor. You are a doubter, they are the teacher. You aren’t trying to convince them, they are trying to convince you. You need them to explain again, why you should believe in the world of John Lennon’s Imagine, just one more time. Can they do so without lying? Can they even make it believable?

The issue with the Blue-State Boomers is less priorities than moral concern. The Blue-state Boomer has a poor ability to recognize their political opponents as moral objects, as people who have legitimate concerns. The progressive narrative always conceives the reactionary as something outside of humanity, an obstacle that needs to be purged. Despite the flowery language, the internal dehumanization of the non-believer is ever-present. Your goal in conversation is to shatter this narrative perspective. Strive for a frame where they need to convince you of their progressive dream, slowly reveal you reactionary values, then force them to make your wrong-think part of their idealized vision. Is there a place in their Utopia for people like you? It sounds small, but it is a crack in the dam, and from this crack all future results will come. Perhaps understanding? Perhaps sympathy? Perhaps a re-thinking of their ideology itself? Slowly the thread of puritanism unravels, a doubter one moment is a reactionary the next.

I suppose here, in closing, I need to defend the shaky premise at the foundation of this article. I get the sense that any young dissident, in particular any Zoomer dissident, will voice a rather acute objection to what I said here:

Alright Dave, point taken. Certainly the Boomer generation is one of the biggest barriers to significant change. Obviously, nothing can get done until they are out of the way. Obviously, we can’t help but talk about this subject. But why the call for discourse? Isn’t this is simply an experiment in managed futility, looking to improve the efficiency of an endeavor that is, by your own admission, quixotic. Old people are almost impossible to convince. Certainly the tried and true method for generational change is less conversation than longevity. We just need to wait for the retirement (or perhaps the death) of the older generation. Then we will usurp their positions, over their very silenced objections.

And I have to grant this may be how the “Boomer Question” resolves itself. Such is the way of nature and I am not one to argue with its designs. Ultimately time will grant victory to the young over the old and nothing can stop that. But here, I would ask my readers to consider the benefit of discourse between generations, even if it occurs rarely, and mainly as a futile remnant of a dying tradition.

As dissidents (right-wingers of a sort) I think it is clear that we are missing something. There was a generational pass-down of responsibility, tradition, and wisdom that occurred throughout our civilization’s past that has, in this historical moment, been stopped. What past generations received by inheritance, we will have to build ourselves. What past generations could rely on as true moral axiom, we will have to re-derive and re-sanctify. What our predecessors could understand through teaching, we will have learn through hard experience. And it’s on this last point, we should pause.

Often, we look to discourse(rightly) as a zero sum game of rhetoric. But on a deeper level discourse has a didactic quality. Conversation sharpens the mind and spirit. It gives insight especially when we attempt sincere communication with people far removed from us in age and experience. As they say, the past is a foreign country. Even though the ways of the Boomer are backwards and manifestly unsuited for the world of today, they have learned many things across their decades of life. And just like a perennial flower, the folk wisdom now sterile in the soil of the present might bear fruit when the spirit of the age changes. Any leader looking to build something lasting must take this possibility seriously.

In my experience, there is a critical piece of classical wisdom which under-girds all attempts to communicate with elders. Despite the ultimate outcome, the old can grant irreplaceable wisdom that will enrich our lives as we inevitably age and take their place as the older generation. This insight is valuable, we just require the patience and understanding to receive it.