The following is a rough transcript which has not been revised by The Jim Rutt Show or Jeff Giesea. Please check with us before using any quotations from this transcript. Thank you.
Jim: Today’s guest is Jeff Giesea. Jeff is an entrepreneur and operator in media tech by background. He is also a writer and thinker about social change, information warfare, and national security. He is the founder of the Boyd Institute, a policy lab for America’s future looking at bold asymmetric solutions for the decades ahead, focused on tackling gerontocracy, overregulation, and social fragmentation. Welcome, Jeff.
Jeff: Thanks, Jim. Great to see you as always.
Jim: Yeah. I’m looking forward to this conversation. For those who want to get more of the Jeff Giesea perspective on the world, you can check him out at @jeffgiesea, G-I-E-S-E-A, on Twitter. And you can also do as I do and subscribe to his Substack at jeffgiesea.substack.com. In fact, it was reading one of his Substacks that caused me to reach out to him. He very recently—what, a day or two ago—published an essay called “Dionysian Futurism.” Tell us a little bit about what you were thinking and where you were going with that.
Jeff: Like you, Jim, I like thinking big ideas about the future. And I tend to be pro-technology. I think we share that as well. And there has been a movement in Silicon Valley of so-called techno-optimists, and I’m generally sympathetic to their perspective that they want to advance technology they believe will be more positive for humanity than negative for humanity. However, as I was looking at all of their images of the future, all of the images they would post about the techno-optimist future, I noticed they were lifeless, sterile, completely orderly. They looked almost cyberpunk, but they also looked sterile. And I thought, what’s up with that? And somebody else actually made that observation that stuck with me.
And then I was reading some different essays on Substack over the weekend, and something clicked. What was missing was Dionysian energy. And what I mean by that—as you may know, the philosopher Friedrich Nietzsche wrote a book called The Birth of Tragedy, and he talked about the two central drives of civilization as these Greek gods: Apollo on the one hand, that’s order, reason, structure, and Dionysus on the other, that’s the wine, laughter, irrationality, chaos. And his argument was that we need both of those energies to propel a civilization and high art. He believed that the West was suffering from a lack of Dionysian energy, that that vitality had gone too Apollonian.
And that frame was useful. As I looked at these images, I thought, oh, that’s what it is. They’re all Apollo, no Dionysus. So where are the humans? Where is the joy? Where’s the laughter? Where’s the sex? Where’s the feasting? Where are the intimate conversations and picnics in these visions of the future? The things that make us feel human and alive. And I saw a huge blank space there, and so I thought, I’m going to put a stake in the ground and make the argument that we need Dionysian futurism. We need to train our brains to imagine futures where we can actually see ourselves enjoying our lives and where humans are at the center of it still.
Jim: Yeah. I like it. I’ll point out it’s not just the techno-utopians. The world I tend to hang out in—the Game B world and the adjacent spaces of social change that are a little bit more hippie-ish, I would say—they also tend toward art and writing that focuses on quietude, you know, people meditating or doing yoga or Tai Chi or something and holding hands in a circle. They don’t have enough conviviality. They don’t have enough drinking and partying and people humping in the bushes. And I’ve been pushing the idea that real face-to-face conviviality is perhaps the thing that we’re missing most in our society. I find that when I meet somebody face to face, my relationship with them is just fundamentally different than if it’s only been virtual. You know, we’ve met once, had a really nice lunch a few years ago, and I’ve always thought I knew you way better than the people I’ve never had that experience with. And I think you hit it right on the head—for whatever reason, the intellectual leaders of our society in particular have been pulled into an Apollonian perspective where it’s all in the head, not in the groin.
Jeff: Right. Or in the heart.
Jim: Yeah. Or the heart.
Jeff: I think there’s an important distinction to make. When I floated the idea before I wrote my essay, one person said, well, I fear that our version of Dionysian future would be, you know, everybody’s obese, eating all the time, and addicted to dopamine and OxyContin or something like that. And I thought, woah. Ouch. That is a fear. And so I think there’s a distinction to make that Dionysian futurism, as I argue, is an open invitation. I’m not defining what it means. It’s for others to define. I think we need more people just thinking about it in general.
That being said, I want it to be positive—not utopian, but positive. And I think there’s a distinction between Dionysian energy that is life-giving and full of vitality, and Dionysian energy that is kind of dystopian and that takes away from life, that numbs life rather than enhancing it. So people will interpret that in different ways. Some people might think drinking alcohol at all numbs life somehow. Others will think, no, wine and laughter and some level of intoxication is part of vitality or conviviality. It’s okay to have those discussions, but I do think there is an important distinction to draw between positive Dionysian energy as I see it and numbness, degeneracy, and addiction that drags humanity down instead of up.
Jim: Yeah. And I think that is an important distinction. I often use the word decadence—that if we take our freedom and we don’t constrain it with some agreements about what the good is, it’s easy to slide into decadence, you know, wire-heading on Twitch and hitting the gambling apps all day long and swiping right—or is it left? I don’t know, I’m too old for that—on the dating apps. These are all kind of decadent ways of living. And it strikes me that what comes next ought to kind of recapture conviviality in its better forms.
And we’re going to talk later a little bit about generational change. I’m old enough to be able to remember kind of the decay in conviviality. My parents were Greatest Generation—actually, my mother was a very old Silent. My father was a GI Joe, born in 1923, and they and their friends were extraordinarily convivial. They were always at each other’s houses, having parties that went on to four o’clock in the morning, even when they were 50 years old. Us boomers, at least since we were in our twenties, would do parties till four in the morning very often. And there was just a huge amount of fun conviviality. They weren’t very Apollonian, I can say that, nor were they decadent in their Dionysianism either. And the boomers were less so. Well, the Silents were less so, and the boomers were even more or less so. And then Gen X and now the millennials—it’s like we’ve run downhill on conviviality over the last few generations.
Jeff: Well, I mean, first, it’s kind of funny—every time you say “conviviality,” that word sounds so Apollonian to me. So I would push back on that. I mean, obviously it has a Dionysian meaning, but I almost feel like “fun” or “passion” carry that sound more Dionysian. That’s just to my ear.
And then as far as generational changes and how this energy manifests, I think it’s a really interesting topic. I’m late Gen X, younger generation than you, but still on the middle-age side of the equation these days. And as I look at younger generations, there are these statistics about Gen Z having less sex than any other generation and not going on dates and stuff like that. And I try to sympathize because on the one hand, I think their forms of engaging in Dionysian energy have changed and evolved—that’s perfectly okay. On the other hand, I think the structure of life shifts how these things manifest. So if you have a lot of debt, and then on the other side you have all these dopamine traps and addictions, and everything’s done virtually instead of face to face in apps—how do you make space for a healthy Dionysian energy? I would argue for younger people, that’s a harder needle to thread. And so they either air on the side of decadence—to use your word—numbing themselves with video games all day, or whatever it might be, and just being overweighted Apollonian on the other side of it.
Jim: Yeah. I think, of course, as always, how we behave is conditioned by our culture. And we are currently in a culture where we’re being rained on with dopamine attractors, where the game is rigged to try to make everybody in debt in a major way. I mean, when I went to college, our local good state university cost $600 a semester, I think it was. And I went to an elite college and it cost me $16,000 for four years, including room and board, which is of course a tiny fraction of the $320,000 or whatever it would cost at list price today.
Jeff: Yeah. There’s a joke about boomers buying their first houses for, like, four huckleberries.
Jim: Yeah. I didn’t buy a house till late. My wife and I decided to stay footloose and fancy free and rent until I was 32 or 33. But I certainly had friends that bought houses for—say, what would that be, 1975—$50,000. You could buy a decent house. Nothing fancy, it’d be like 1,200 square feet or something, but you could buy a house for $50,000, and that would be equivalent to five years’ starting salary for a new college grad. That would be stretching it a bit, but with two fresh college grads making $20,000 a year, you could afford a $50,000 house. Now the average house is about $350,000, and the average starting salary is $50,000. Well, the ratio isn’t that different, actually.
Jeff: Yeah. I wouldn’t go too far down that path of conversation. We can move on from that topic.
Jim: Well, let me toss another one that’s closely related, and this is a graph I’ve been following for years. Back in the day, 85 percent of college freshmen believed that having a meaningful philosophy of life was of top importance, and those who thought being financially very successful was very important was like 35 percent. Today, it’s almost reversed. Only 40 percent think that having a sophisticated philosophy of life is important, while almost 75 percent believe being very financially successful is important. So the context in which we sort out our priorities has changed in a fundamental way where financial success is much more salient than it used to be.
Yeah. I remember when I graduated from college, I didn’t go on a single job interview, didn’t go to the placement office, hitchhiked around the country for a couple of years, basically just fooled around. And that was a little bit more extreme, but it was not that uncommon in the day. We weren’t all that worried about it. We didn’t really care. That may have been that the world was easier and we knew that if we got back on track we could take off easier, or it may have just been a different cultural time with different values and different status games.
Jeff: Yeah. I mean, I think it’s some combination of both. And again, I think it’s really dangerous for boomers to kind of say, “Back in the day, when we were like this,” and not understand that tuition has gone way up and the pressures on students to repay their student loans mean that of course they’re going to be more concerned about making money than they were in the past. Our society with globalization—there are just increased economic pressures. We have a housing affordability crisis. I mean, you talked about buying your first house late at age 32. I think many young people would listen to that and hear that as early. Being able to buy a house at 32 is kind of a privilege.
At the same time, I’m fully with you in terms of the importance of figuring out what the good life means and taking time to travel. I’m kind of on a bridge between the boomers and the younger generation. And I think I’ve written about why the humanities, why studying philosophy, why reading great books in this moment—especially as AI washes over the world—is so important. And so I wouldn’t be surprised to see young people in the last ten years starting to question the whole value proposition of college. I think they’ve started to question the structure of society and why it is so weighted to the old, for example. And then I think AI has introduced so much career uncertainty that they’re having to ask hard questions sooner about what it means to live a good life.
Peter Banks, the new president of the Boyd Institute—we had a livestream yesterday, and I was telling him how I read this Substack post about a guy who’s hiking the Appalachian Trail. He met a couple of different recent college grads, one of whom went to the same college he went to, University of Tennessee, studied business, and decided to go to ranger school. Part of his logic was that being a forest ranger would be protected from AI. And he loves nature, and that’s what he wanted to do. And in some sense, he was able to get to that thoughtful place faster than ten years ago he might have gone and worked for a big corporation or something like that. So I do think young people are going to be forced to ask harder questions sooner than maybe they have in the last twenty years. So I see a resurgence of the humanities, a resurgence of asking philosophical questions coming, at least among thoughtful young people.
Jim: Yeah. I’m seeing the same. Our Game B movement attracts a number of very thoughtful young people, and it’s been great to see. I’m going to make one comment about conviviality, and then I’m going to move on to the humanities revolution. This is just a little tip—the old dude telling what he thinks is cool about real conviviality—and that’s the contrast between the dinner party and meeting your friends at a restaurant. Since the sixties, it was probably 75 to 80 percent dinner parties, right? Where people come over to each other’s house and somebody cooks, or it might be a potluck, whatever, but they don’t go out to a restaurant. Now it seems like it’s 80 percent going out to a restaurant. And I look back at that change with a wistful sense of loss, because a dinner party at a home is somehow a much more convivial event than meeting up at a restaurant, and it’s easy to do. Anybody can throw a dinner party. Right?
Jeff: Yeah. I mean, that’s interesting sociologically. Because I think for me, I love dinner salons and having that space where people can come together over a meal. I’m agnostic whether that’s at a home or a restaurant. If it’s at a restaurant, that’s fine too. If it’s at a home, that’s kind of good. But I was having conversations with friends in Washington about how the culture of hostesses and Georgetown dinner parties has gone away and what we’ve lost as a result. We used to have these private dinner parties where Democrats and Republicans would come together and socialize, and some hostess—a very powerful, well-known Pamela Harriman-type hostess in Georgetown—would bring them together, and it would be very private, very cordial. And how we’ve kind of lost that in our politics.
And then, you know, you think about feminism, which has been terrific for women in the workplace—I fully support it. But you can also see how that might be a factor in losing the dinner party culture that we had in, say, the fifties.
Jim: Yep. There’s some truth to that. I’m with you—I’m a great supporter of second-wave feminism. Women should be able to do whatever they want to do in the world. Right? But we should also acknowledge that the elimination of the stay-at-home mother—though of course we now have some stay-at-home fathers—does come at the cost of the social infrastructure.
Jeff: Because it was the women that did a lot of that. Though I will say, I do a lot of the cooking when we have a dinner party—not always, but sometimes. Well, and I think there’s a pro-social role—where I violently agree and maybe where we’re landing together, I’ll throw this out—is bring back the host. Let’s bring back the hostess. Doesn’t matter if they’re men or women. Bring back the idea of somebody hosting something, bringing people together over a dinner salon. I know in my history I’ve never been a big party thrower. It’s just not my personality, and I get nervous about it. I did professional events. But hosting dinner parties and salons where there’s some topic of discussion, you bring people together, maybe eight or 12 people—I love doing that. It’s so much fun.
Jim: Yeah. And it’s an art form. There are two parts to the art form. One is the curation of the right people. When my wife and I do it, we’ll discuss for quite a while who are the right eight people. And then the second is the actual hosting—to make sure that some bore doesn’t dominate the conversation, might be me, and that everybody gets a chance to speak and that the topics move along, etcetera. You have to do it, of course, so subtly that nobody even notices. Right?
Jeff: So, Jim, just to turn this around—what makes you decide to host a podcast as opposed to more dinner parties?
Jim: That’s a good question. Frankly, logistics. Logistics and the topics that I want to do a podcast on. I live in a very remote place in Appalachia, and yet I’m interested in cutting-edge technology, social change, and philosophy, and there aren’t too many people interested in those topics on the ground here in Appalachia. And so it’s just a very natural thing for me to do a remote podcast around the world on the topics I’m interested in. I’d also point out that I do my podcast during the day almost exclusively, so it doesn’t really conflict with the idea of doing a dinner party, which we still do.
Jeff: Yeah. Fair enough and fantastic. And I think that’s a tension I feel and that many people feel, where so much of our civic life has migrated online. What are—in addition to just bringing back dinner parties, like you said—what are new forms of that online that are possible? I think there’s a lot more experimenting that can be done even with Substack lives, and it’s not going to be the same as sitting around the same dinner table and so forth, but you can replicate some of that with online spaces. So I fully support virtual hosting as well.
Jim: Yeah. And I will say I have not done as much of that as I probably should have. I’m going to have to look into the—what did you call it? The Substack lives?
Jeff: Yeah. Livestream. I think that form has a lot of opportunity to experiment. Right now, it’s very Apollonian, you could say. But I wonder how you can make it more Dionysian, how you can make it more of a salon-like space with multiple people instead of just one on one, and bring back some convivial spaces, you might say.
Jim: I’m going to look into that because I’ve only recently moved my podcast to Substack, and I haven’t really explored all the affordances of Substack yet. That sounds like it could be fun. Alright. Well, let’s move on to the next topic, and this was another one of your recent essays: “The Humanities Revolution Has Already Begun.” Let’s talk a little bit about the retreat of the humanities first, and then the signs that you have found that the humanities are coming back, though maybe not in the same form that they were in before.
Jeff: Yeah. So I recently discovered this nonprofit called the Kairos Project, and I love it. I think it grew out of St. John’s College, and it’s all about reading the great books. They organize decentralized, open-source book discussion groups. So it’s very Jim Rutt on-brand organizationally. And so I joined last fall. I joined one of their groups that was reading von Clausewitz’s On War. And then after that, I liked it so much—I was like, wow, great books—I decided to lead one, and I led one on Hannah Arendt’s book The Human Condition. She wrote that in 1958 in the wake of Sputnik, which was a huge cultural shock. Man going into space, and the Soviets were doing it faster. So it was both technological and geopolitical. And she was trying to figure out what does it mean to be human now in this new technological era. Obviously, it seemed very relevant to 2026.
And I realized with all of the AI stuff—machines are becoming smarter than humans for the first time, ever evolutionarily, in some areas at least—there’s an open question of what does it mean to be human? What does a good life mean or look like? So I see technology forcing a lot of philosophical questions. And so I was like, wow, there should really be a humanities revolution. And then I looked around, and one day I was in my Kairos Project group moderating a discussion, and I looked up and I was like, wow, there already is a revolution, and I’m already part of it. It’s not everybody. It’s not widespread. It’s more than two percent of the population. But you see young people reviewing great books on TikTok. Any great classic work you want, you can find on YouTube. The Kairos Project hosts hundreds of these book discussions with participants from all around the world. So I realized it’s global, open-source, highly democratic, and happening outside the university.
And so I thought, wow, this is kind of cool. Is it scholarly? No. It tends to be more amateurish, but it’s also more democratic and it feels like the tent revival movement. There’s an earnestness and a bottom-up aspect to it that I think is really exciting.
Jim: Good. And the thing about it being public and not scholarly is actually important. If we go back to the great original classics—Homer, right, in the Western tradition at least—the bards came around and recited those works from memory, and everybody listened. So the common material for discussion and analogy and metaphor for the whole Greco-Roman world was Homer, basically, and not just the scholars. And that’s something that we lost with the universitization of the humanities. And people forget how recent that is. The great writers were not college professors even in the nineteenth century. There were people like Thoreau or Melville or what have you. The twentieth-century turn of the humanities to the university is a historical anomaly.
Jeff: Yeah. And I looked at Substack, where I like to write—so go sign up for my Substack—it’s almost like, and I don’t want to overstate this or be too cute, but it’s kind of like the Renaissance. It’s like Renaissance Florence. You have a flowering of essay writers who are writing earnestly about philosophy and great books and all these different ideas. And that’s just a really interesting cultural space that’s been created there.
And I think also when it comes to the humanities, even myself—I find myself gatekeeping myself. Like, who am I to lead a discussion on Hannah Arendt? I don’t have a PhD. I didn’t take that path. But I think it’s really important for people not to gatekeep themselves and to realize that great books are a river that we can jump into anytime we want in different phases of our lives. I haven’t jumped in it in a couple of decades, but I can jump in and have that conversation with great minds. It’s there for me at any time, and it’s there for you as well. And I think that accessibility—not being afraid to jump in that river, not feeling like you have to, but knowing it’s there for you—when you want to commune with great minds, it’s going to hit you differently in different phases of your life. Jump in.
Jim: That’s interesting. Probably unconsciously, what you are seeing gave me a call about a year and a half ago, and I went back and read the Iliad in two different translations. And, woah, it really ignited something for me because I do recall that the Iliad was often considered the source waters for Western civilization. And the intensity of it, the vividness of it, and also the strangeness of it—these were Bronze Age people who thought rape and thievery were honorable occupations. When Achilles was not busy fighting major wars, he basically bragged about the sheep he stole and the women he kidnapped. Right? And this is very, very different. It really takes your brain back to before civilization had done its thing on us. And it’s, I think, really important to remember, to learn about the vividness of ways of life other than our own.
I then went on to read the Odyssey, which I’ve always liked. And right now, I’m just about done with what I would call a new classic, Zen and the Art of Motorcycle Maintenance. I don’t know if you’ve ever read that. I read it twice before, but not in forty years. And I must say, I’m taking much more out of it this time, and I’m really, really enjoying it.
Jeff: Check out the Kairos Project. I mean, I think you would love it if you’re not familiar. Again, the classes are free, and they have core curriculum stuff. So they have core curriculum groups that focus on timeless classics like the Odyssey and the Iliad and Plato’s Republic. And then they have general book discussions where, as long as it’s a great work, you can go and read The Brothers Karamazov or Emma or whatever the work is. I’m leading another group this summer session. I think they just opened summer enrollment. So go check that out.
I will say, you might find this story funny, Jim. I was at a party in Washington once, and I thought I was showing off somehow—the Odyssey came up, and I recited the first verse: “Sing to me of a man, Muse, the man of twists and turns.” And I thought I was so cool for remembering that. And the person I was with recited it back to me in ancient Greek. And I was like, woah. I’m not worthy. Slam dunk. That was so good.
But another point I want to make about reading great books that I’m noticing just as I’m doing it—getting the paper book, writing with my pen in the margins—it is the perfect balance for me with social media. I know you take social media breaks, and we both struggle with our relationship with it on some level. Reading great books in paper form, you have to really focus. My mind has to just shift off. Scrolling on social media is high reward in the short term, low reward in the long term. Reading a paper book or a great work is kind of painful in the short term, but has a higher reward in the long term. So I think it’s a really good—I’m tempted to set a rule for myself: every minute I spend on social media, I have to spend an equivalent minute reading a great book.
Jim: That’s actually a great idea. And reading books in general—even if they’re not the great books—is a dying art, unfortunately. If you read the statistics, the number of people still reading books, particularly in the younger generations, is falling off the table. And I continue to be a great reader. I still start around 100 and finish 75 books a year, just as I have since I was 10 years old. And I think reading serious books of any sort, of any vintage, is a far superior way to spend one’s time than arguing with morons on social media.
Jeff: Yeah. And I’ve discovered audiobooks. I would have looked down on audiobooks ten years ago, but in the last five years, I love audiobooks, because I can walk and do other things while I’m listening. And a lot of what I listen to is popular fiction and so forth. But just yesterday, I was starting to explore—hey, what would it be like to listen to a philosophy work on audio? Would that make sense? And I think for a lot of books, no. But for some books, yes. So as an experiment, I started to listen to a famous English actor doing Marcus Aurelius’ Meditations. And I was listening to it, and it kind of did lend itself to audio. I also started listening to Michel Foucault’s Discipline and Punish. And that was fascinating on audio. I mean, it’s gruesome.
Jim: Why? You’re not a Foucault fan?
Jeff: Not at all. If I would consider Foucault an enemy of civilization. Yeah. He’s poisoned the minds of two generations of scholars. That’s just my opinion.
Jim: So yeah. No. I agree. But my deeper point is: even give audiobooks a chance. Nothing replaces the paper copy and writing in the margins, but for some things, I think audiobooks can work for some people too.
Jeff: Yeah. I probably should do it. Oddly, I have some history with audiobooks. I’m the one who approved the first major venture investment in Audible—$10,000,000. And yet I have never listened to an audiobook since I did some testing of the early Audible. So it’s been thirty-five years since I have listened to an audiobook. My wife listens to them. My daughter listens to them. My friends listen to them. Jeff Giesea recommends them. I probably should give one a try.
Jeff: Well, Audible is fantastic. And, you know, being a business guy like you, I look and I realize a lot of these books are copyright-free, fair use. It’s tempting to hire actors and just produce better versions of them, because too many great works don’t have good audio versions. They’re just a computer reading the text. So I think there’s an opportunity to make them even better.
Now, something you mentioned in your essay was the turn of the humanities in the universities that frankly turned a lot of us off from the humanities. Talk about that a little bit.
Jeff: Yeah. So I arrived at college in the mid-nineties at Stanford, and Stanford tended to be pretty ahead of the curve in terms of a lot of the woke trends. And I was wrapping my head around them because I’d been raised in a more traditional twentieth-century model, and some of it made sense to me—I like diversity and open thinking. Some of it didn’t make sense to me, and I ended up getting involved in the kind of right-wing student rag that was quite critical of a lot of those trends.
Fast forward—the woke stuff really grew in intensity, and a guy named Jacob Savage recently wrote a piece called “The Lost Generation,” and he wrote about this lost generation of millennial white men in particular. I think beginning in the late nineties, you started to see systematic discrimination against certain categories of people. If you were too white, too straight, too male, that was bad. And you can understand why departments would want to increase their diversity—that’s not a bad objective—but it became systemic discrimination. And then at the same time, the ideology skewed so far left that a lot of these departments barely had any Republicans. Nobody expects the humanities department to be perfectly balanced, but I think we’ve seen universities in the last thirty years just skew so far left that they’ve marginalized any conservative or right-leaning voice out.
And so a lot of those people changed their path. I would push back on Jacob’s framing and say it’s not a lost generation. People who would have gone into academia or journalism a generation ago are saying, you know what, I’m going to go to Silicon Valley and start a startup. I’m going to go into finance and then do this stuff on the side. So my generation in particular and younger—you start to see these people who don’t want to, they’re not the most persecuted people in the world, I don’t think they’re dwelling on that, but they do have a little bit of a chip on their shoulder towards universities and are like, we don’t need universities anymore. We’re going to go be creative and do podcasts and YouTube videos and host our own book discussions on our own.
And so the flowering of this humanities revolution—one of the causes I mentioned in the essay is that. Another cause, of course, is just digital technology. Having Zoom and digital technologies makes it possible to do these courses. And then the third driver is AI. It’s just forcing some of these questions.
Jim: And it is interesting. AI has its risks, its negatives, but it also has its positives. I know when I’m reading a serious book, all day long I’m hitting either Perplexity or one of the other big engines—often Google, sometimes ChatGPT—and getting a deep gloss on a single word sometimes. What does this really mean? And I’m finding that AI and related technologies are really a great help for us non-experts to read these very difficult books. I’ve probably done ten such side researches while reading Zen and the Art of Motorcycle Maintenance, for instance.
Jeff: Yeah. I mean, the Kairos Project would say that’s bad, that you should just stick with the text and not use these secondary sources or let AI tell you what to think. So people have different philosophies about how to use AI, and sometimes the debates get overly tactical. Like, some people are like, oh, you should never use AI for writing ever. And others are like, well, I can have it edit and cut words or get ideas to strengthen an argument. I find a lot of those debates pretty silly.
I think AI is pretty incredible. The question that I would ask if you step back is the one that Hannah Arendt asks: when does technology empower us, and when does technology enslave us? When are we offloading cognitive load and learning from it, and when are we delegating our actual critical thinking? And I think a lot of philosophers think that we’re delegating too much of our critical thinking to AI, and there’s a valid critique there. I would argue that there’s another perspective: how much is AI reducing our cognitive load to be able to think about interesting things? Like, driving a long distance trip twenty years ago, you had to spend a lot of your cognitive load on your map figuring out where to go. But because of Google Maps, you don’t really have to think about navigating. Your mind is free to think about other stuff. And in the same way, I think technology or AI could move some people up this pyramid towards more and more critical thinking rather than, you know, how do I write this code?
Jim: It’s like, what should the right prompt be? I’m a user of AI a lot for all kinds of things—code, writing, etcetera. But I do think that you have to keep in mind what you’re trying to do. And actually, Pirsig in Zen and the Art of Motorcycle Maintenance has a concept called quality, right, which is very confusing, but I think I finally got my hands around it. And if we use quality as our North Star, then I do believe it is safe to use AI for all kinds of things. It’s a better copy editor than I am—not as good as a professional copy editor, but better than I am at the sentence level. So I’m going to use it for that. It’s also amazingly good for doing very deep research. It’s also very cool for combining two ideas that don’t seem to be related and finding the connections between them. On the other hand, if you have it just write something for you, it will suck. It’ll just be bland and not sharp. At least currently—that may change. So it seems to me one needs an extraneous measure, and something like quality strikes me as not a bad one.
Jeff: Well, this is why you’re hearing “taste” as a buzzword in Silicon Valley. Taste is basically the same thing as what you’re saying. Like, if you have good taste, you know what good writing looks like. And I think one of the concerns with AI for young people is they haven’t gone through the analog education you and I have, so they don’t even know what good writing looks like absent these computers telling them what to think. So it’s an interesting discussion and debate, but I’m broadly pro-AI for sure. I just want to make sure we’re using these tools to preserve our ability to think, our ability to act, and our ability to love and enjoy life.
Jim: Well said. Well said. Let’s move on to our last topic. We’ve got about ten minutes here. And that is you’ve recently written three essays on the goddamn boomers. Right? The three essays are “The Boomer Reckoning No One’s Ready For,” “Boomer Caregiving Will Wreck Our Politics,” and the most recent one, “The Long Boomer Farewell.” I should confess to being one of those dread boomers, born in 1953, though I still act like I’m 14.
Jeff: You’re a boomer, Jim? Wow. I didn’t realize that. You’re like a proto-boomer. You’re a turbo boomer.
Jim: Turbo boomer. Do you buy Skechers? Do you wear Skechers these days?
Jeff: I have nine pairs of Skechers in my closet. Right? I’m the guy in those Progressive Insurance ads. “You don’t want to turn into your parents.” I’m the parents.
Jeff: Well, yeah. So I mean, first of all, I live in the shadow of boomers. I’m Gen X, and my parents are just on the outer fringe of boomers. So it’s easy for my standpoint to be resentful of boomers for hogging the spotlight, for being the Marsha to our Jan in Brady Bunch terms. But as I stepped back, I realized I actually have a lot of boomers that I love in my life. And I like boomers, but they kind of annoy me. And I came up with this thing called the boomer paradox—that boomers are holding us together, but they’re also holding us back.
And I realized that the next twenty years of America, and indeed a lot of developing countries, is going to be defined by boomers retiring and fading into the sunset. That’s what I call the long boomer farewell. The Greatest Generation—you may recall in the late nineties, Tom Brokaw wrote the book, we celebrated them as the greatest generation, there were movies like Saving Private Ryan—it was celebratory. It was a moment in time, and it was a pretty clean transition, I think. The boomer transition will not be like that. I think it’s going to take place over an extended interregnum. I think culturally, it’s more complicated. We’ll miss boomers, but I don’t think anybody’s calling them the greatest generation, although they think they’ve contributed a lot. And I think unlike the Greatest Generation, this boomer transition is civilizational in effect because it’s tied to entitlement spending, the labor market, housing, geopolitics, and so many other issues. I think it’s really a defining twenty-year interregnum period that we’re facing.
And as I think about it, the key question that we’ll have to answer is a game theory question. As it stands right now, in five years, there are going to be more Americans 65 and older than 18 and under. That’s really a problem for democracy. We could easily—if we’re already not a gerontocracy—be five years away from complete gerontocratic capture. That is unhealthy. When we’re spending $6 on old people for every $1 on young people, when all of our entitlement spending is going to the people who are the wealthiest in society—we want to give them dignity, but there’s something a little bit out of whack there. And if we keep going down the path that we’re on, we’re entering a period of managed decline that’s going to lead to financial insolvency. And boomers will continue to vote for their interests by and large during this period.
What I advocate is active reform. I don’t want to declare generational warfare. I like boomers. I want to do right by them. I want to recruit boomers and other generations to help us rebalance the portfolio of generational power, thinking about their legacy and what they want for their grandchildren, and making sure that the future they leave behind is not robbing the future from their own grandchildren. So I think enlisting and recruiting boomers to help proactively address some of these issues and rebalance power in society—so that we can actively reform the country and provide a future for young people—is a wide-open question, and in my opinion, a hugely defining issue for American civilization.
Jim: Yeah. I absolutely agree, by the way. I just happened to read an article—maybe it was in the Wall Street Journal—that with the next cost-of-living adjustment, a couple at the top of Social Security—and actually it wasn’t the top, it was people who retired at 67, not at 71—will have a Social Security pension of over $100,000 a year. That strikes me—and these are mostly the higher-income and wealthier people, because you earn your Social Security by how many years you work, how much money you make, how much you pay in, all this stuff. So the people who need it the least are going to be getting the most. $100,000 a year. That’s like, what the hell? And I look at other advanced democracies, even welfare states in Europe, where the average top couple benefit is more like $50,000.
And you referenced, at least indirectly, why the gerontocracy is so strong—us old farts, we vote. Goddamn it. So the first step for the younger generations is to organize. I think you pointed out in the conversation we had recently: there is no AARP for young people. And young people need to sort of see what’s going on and that it is a generational tug of war to some degree. And if they don’t pull their end of the rope, they’re going to get the short end of the stick.
Jeff: Yeah. And like I said, there’s no AARP for young people. I’m walking the line between old and young myself. I don’t want generational warfare. I don’t want candy for Gen Z—identity politics for generations is kind of where we could be heading. But I do think we need to rebalance generational power and do it quickly and proactively if we’re going to avoid that kind of tug-of-war issue.
And one of the effects that we’re seeing right now that I think is dysfunctional is property tax relief. Even millennial governors like DeSantis—or Gen X, you know—they’re still pandering to their demographic of retired boomers by offering property tax relief. Well, I’m all for low taxes, but if we’re giving boomers relief instead of young families that are trying to have kids and enjoy life—why are we orienting our housing market around the needs of wealthy boomers instead of young families? Why are we trying to relieve property taxes while our schools suffer, for example? So I think that’s an example of the distorted effect of gerontocratic capture.
Jim: Yeah. And particularly bad in California, where they have these really crazed real estate caps and such. The boomers can be sitting in their $3,000,000 houses paying taxes as if it was a $300,000 house while the schools go to hell. California used to have the best schools in the country. Now they’ve got some of the worst. Those caps were enacted back in the nineties, and whether it was actually generational warfare at that time, I don’t know. But that’s been the result, and it’s almost impossible to repeal.
Jeff: Yeah. In my essay about how boomer caregiving will wreck our politics, I just realized how much cognitive dissonance there is in our society on these issues. For example, I spend a lot of time in Florida, and I know all kinds of Fox News boomer men in Florida who are like, “Deport the illegals.” They fully support enforcing the border and deporting illegal aliens. And yet they employ—I point out, like, well, what about your landscaper, or what about your nurse’s aide? And they’re like, you know, if ICE came for them, they’d probably protect them, defend them, try to help naturalize them. So there’s this interesting disconnect between what people say they want policy-wise and what they actually do in their lives that I think is interesting to note.
Jim: Yep. Indeed. Let me put a little highlight on the difference between Gen Xers and boomers. The oldest Gen Xers are now 61. And not only have they not elected a president, they haven’t even had a serious contender for the presidency from the Gen X generation. While the boomers have already had four presidents. Bill Clinton was 46. Obama was 47. George W. Bush was 54. The boomers came to power very early.
And then I was also thinking about the social changes that occurred. One of my favorite hinge people in literary fiction, of course, is Don Draper in Mad Men. I tried to estimate when he was born. My best guess was about 1923. The show started in the nineteen sixties, so I made him in his late thirties. And yet by the end of that show, he was a boomer in values. The boomer values just swept through and pushed out all the Greatest Generation values, at least amongst the elites. And then the boomers went on to dominate music and culture and everything else, and nobody’s been able to—the way we pushed out the power of the Greatest Generation and the Silents, that never happened to the boomers. Any thoughts on why that was?
Jeff: Well, I don’t know if I agree with your analysis. I agree with the first part, which is so many of the presidents—I think there were many of them born around the same year, around 1953 or ’54, something like that.
Jim: Actually, most of them are early boomers, like ’46, ’47.
Jeff: So a lot of them were born in the forties, but yeah, a lot of them were born from the nineties through today—we’ve had presidents born effectively in the same years. And so I think boomers have been a big generation. I would say they’re narcissistic in some sense. It’s a very self-centered generation. They always have been, and they’ve contributed a lot culturally and economically, and they’re living longer lives by at least ten years from their previous generation. And they’ve been part of these massive social changes, some of which have been quite good—women’s rights, civil rights. They’ve contributed meaningfully to society in many ways. You could argue they’ve pushed things way too far in certain directions, and I probably agree.
But I also think, by and large, they’re not really good at—and I’m grossly generalizing here—they haven’t really stepped away. They sometimes cling to power. And in my model, there’s like—you’d appreciate this—there’s the good boomer and the bad boomer. The boomer who knows how to be a tribal leader or elder, who there’s nothing better than finding a boomer who is able to become the chairman and support you and nurture you and not hog the spotlight, but actually knows how to play that role of a tribal elder—versus boomers who just cling to power and position and want to be the center of everything to the point where it’s like, you need to go. I mean, even now, I was listening to something this morning about a 92-year-old federal judge. I don’t want to be ageist, but why do we have judges who are in their nineties? That’s kind of weird.
So boomers—I love them, I think they’ve contributed a lot, I think all generations have shadow sides. I think they have a narcissism issue and kind of a question of how to be tribal elders. They’re not necessarily thinking about giving power to younger generations proactively.
Gen X is much smaller. I think we’re well positioned to be generational brokers. I think Gen X has built Silicon Valley and has changed the world in other ways through technology. I wrote this piece called “The Broligarchy Will Either Save the World or Destroy It,” and it made me culturally analyze my own generation. And I realized—if narcissism is sort of the sin of boomers, grandiosity is the sin of Gen X. Because we pretend like, oh, we don’t care, we’re detached. The goal of boomers was like, let’s have a three-car garage and a 5,000-square-foot house in North Dallas, and one of our cars is a sports car, and let’s go to the country club. For Gen X, it’s more like, I don’t want any car, I want to walk to work, and I’m building this technology that’s going to take over the world or get us to outer space. Elon Musk is a proto-Gen X figure who you can’t imagine contributing to the ballet in San Francisco or doing something in his own backyard, but he wants to get humanity to space—an intergalactic species, as he would put it. So there’s a certain grandiosity in Gen X.
And we also came of age in the eighties with the Cold War and good versus evil—Rocky, Wolverines, fighting communism, that kind of heroic insurgent struggle—and then entered the early nineties with Reality Bites. And so you see that attitude in older Gen X. And then the late nineties, it was like, we’re at the end of history, and technology is going to change the world. There’s no geopolitics anymore. Let’s go build startups that change the world. And that became some of the ethos there. And a lot of good has come out of that, but definitely some blind spots. One blind spot I think we’ve seen in Silicon Valley is just geopolitics.
Jim: But that’s—you know, the last five years, I think people have recognized that blind spot and started to address it. Yes. I’m going to add one last bit, and then we can wrap it up, which is you describe narcissism as the representative failure in boomers. It’s funny—when I was thinking about this podcast this morning, I identified hyper-individualism as the boomer failing, that we went too far with “do your own thing,” etcetera. And I suppose that could look like narcissism and maybe even turn into it. But I think the root is one level deeper, which is pulling away from the tribe and the community and the extended family, and representing oneself very strongly as an individual—that’s probably the thing that differentiated the boomers from the generations that came before more than anything else.
Jeff: You know, that’s interesting. I’d have to think about that. Looking at boomers from a younger vantage point, they seem to have some of that social civic fabric and memory of twentieth-century America—of what that was like—that is lacking among younger generations. So I don’t know if I see that as a major failing of boomers. I mean, I do recognize that in the eighties, half of our parents got divorced, and Phil Donahue was on, and Oprah was on, and they were preaching individuality stuff that had a certain effect on our social fabric. But today, I don’t know if I see that as its biggest sin.
I feel like boomers aren’t able to—I wish they would be more thoughtful about rebalancing power and thinking about younger generations and leaving the world better. I just wish they were a little bit more proactive about transferring power and more gracious about that. So I’ll leave it at that.
Jim: I agree with you, actually. I think the whole idea of an 80-year-old president is nuts. Right? As you mentioned, a 90-year-old judge. It ought to be something like a mandatory retirement for any senior government official. Anyway, you have to run. We have to wrap this up. I want to thank Jeff Giesea for an extraordinarily interesting conversation across multiple fronts.
Jeff: Thank you, Jim. It’s great to catch up with you as always.