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From Here We Go Again With Kal Penn: Will Technology Replace Us? with Jacob Goldstein - What's Your Problem? | Wave AI Podcast Notes

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From Here We Go Again With Kal Penn: Will Technology Replace Us? with Jacob Goldstein

What's Your Problem?

Thu Mar 26 2026

Summary

Podcast Summary: What's Your Problem?

Episode: From Here We Go Again With Kal Penn: Will Technology Replace Us? with Jacob Goldstein
Host: Kal Penn
Guest: Jacob Goldstein (journalist, host of "What's Your Problem?", author of Money: The True Story of a Made Up Thing)
Date: March 26, 2026

Overview

In this engaging episode, Kal Penn and Jacob Goldstein dive into the persistent fear that technology—particularly AI—will replace human jobs. With historical context dating back to the Luddites of the 1800s, they compare past and present anxieties about technological upheaval, examine who wins and loses in these transitions, and speculate on what the future holds for work, meaning, and society. Throughout, the conversation is frank, humorous, and deeply thoughtful.

Key Discussion Points & Insights

1. The Timeless Anxiety: Technology Replacing Humans

Setting the Scene: Kal Penn opens with a reflection on society’s recurring fear of new technology rendering human labor obsolete—be it actors fearing AI, or office workers dreading automation (00:00–02:16).
Quote: “The fear that maybe technology could replace us is like a real thing. It's not just creepy. It feels like it's getting out of control.” — Kal Penn (00:45)

2. The Luddite Parable: Echoes from the Industrial Revolution

Goldstein Recounts Luddite History: Jacob tells the story of the original Luddites—skilled English cloth workers in the early 1800s who violently opposed, and ultimately failed to stop, labor-replacing machinery (12:15–20:06).
Notable Insights:
- The Luddites were not against technology per se, but were skilled workers threatened by sudden technological change.
- They had little to no political power: no unions, no suffrage, leading to their collective, extra-legal response.
- The mythical “General Ned Ludd” was a fabrication, serving as a rallying symbol (15:11–17:15).
Quote:
“What they were doing [was] collective bargaining by riot because there were no unions. They basically didn’t have power in any organized way. So they were seizing power in this collective, ad hoc way.” — Jacob Goldstein (17:40)

3. Comparing Past and Present: AI as the New Loom

Similarities: Worker displacement due to innovation, fear and resentment, potential for large-scale unrest if transitions are too abrupt (22:44–26:09).
Differences:
- Today, workers have more political power (unions, the vote, policy channels).
- AI threatens knowledge workers as well (lawyers, journalists)—groups with traditionally greater political capital.
- Adoption bottlenecks: Despite hype, AI is “still a pain in the ass” to implement for many tasks (24:46–26:09).
Quote:
“For a long time, technological change threatened lower skilled workers… Now it's kind of across the board. And strikingly, people like lawyers and journalists are threatened.” — Jacob Goldstein (23:40)

4. Is Job Loss Temporary? The Case for New Work

Historical Pattern: New jobs previously unimaginable have always emerged after technology-induced disruption (26:20–27:43).
Example: The displacement of millions of US farm workers through mechanization eventually led to a booming labor force in other sectors.
Quote:
“People have been worried about technological unemployment for 200 years… But today, the employment to population ratio… is as high as it has ever been.” — Jacob Goldstein (45:06)

5. What Should Policy and Society Do?

Safety Nets and Redistribution: US social safety policies lag behind other developed nations, making swift adaptation challenging (27:43–29:35).
UBI & Political Realities: Universal basic income (UBI) is discussed more among tech leaders than politicians, with skepticism about its near-term political feasibility in the US (28:56–29:35).
Quote:
“Maybe there's incrementalism, right. Maybe you can get Social Security and Medicare 10 years earlier... It is, in fact, interesting that the people talking the most about universal basic income are AI people and tech people who actually think this might happen.” — Jacob Goldstein (29:13)

6. The Deeper Wound: Loss of Meaning

Beyond Money: For many, work isn’t just income—it’s identity and purpose. Mass technological job loss raises “not just the money” question, but that of existential fulfillment (37:08–39:56).
Quote:
“Work is meaning for a lot of people, right? Work is purpose. Work is just an organizing principle in life.” — Jacob Goldstein (38:32)

7. The Range of Futures: Between Doom and Utopia

Most Likely Path:
- Technological advance is probably gradual, not sudden, giving time to adapt (41:19–44:10).
- Some will learn to use AI as a tool, improving productivity and income, while others may be left behind.
- Impacts will be heterogeneous—not a neat rich-poor split.
Quote:
“You don't want to be competing against the technology, you want to be using the technology.” — Jacob Goldstein (34:05)

8. Hopes and Fears for the Future

Greatest Concern: Rapid, mass displacement could cause political and social instability, as seen with historical Luddite violence (44:25–45:06).
Greatest Hope: Human creativity for generating meaningful new work, even if unimaginable today (45:06–46:35).

Notable Quotes & Moments

On Fact-Checking AI:
“I never take the answer from the AI as a reliable answer. I go and I look it up elsewhere and I look at the source and I evaluate the credibility of the source material.” — Jacob Goldstein (10:55)
On Comedy and Creativity:
“Thank God, AI does a piss poor job at writing jokes. I'm sure one day it will learn.” — Kal Penn (32:12)
AI Art Skepticism:
“There is nothing that I would rather do less on a Tuesday night than come and see the product of you getting high in front of your laptop and pressing buttons. No, sorry, man.” — Kal Penn, on AI-generated art (35:45)
Closing Reflection:
“What a fucking time to be alive.” — Jacob Goldstein (46:39)

Timestamps for Key Segments

Introduction & Tech Anxiety Today: 00:00–02:16
History of the Luddites: 12:15–20:06
Comparing Luddite Times to Now: 22:44–26:09
How AI Might Shape Work: 26:20–30:58
Job Meaning & Policy Responses: 37:08–39:56
Possible Futures & Jacob’s Conclusions: 41:19–46:35

Summary & Takeaways

The cycle of technological fear and disruption is hundreds of years old, recently echoed in AI anxieties.
The Luddites’ story shows the risks for those directly displaced—but also the broader wealth, productivity, and job creation new technologies can eventually bring.
The main challenge: ensuring that transitions aren’t too rapid, and that economic and social support offset near-term harm, not just eventual gain.
Work’s value goes beyond wages; meaning and identity are at stake.
The future likely holds both individual stories of loss and gain, with policy, creativity, and adaptation the key levers for making disruption more positive than painful.

For listeners seeking historic parallels, expert insight, and a candid, hopeful-yet-realist take on the future of work and AI, this episode is essential.

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Transcript

Kalpen (Host) (0:00)

So like, literally a week and a half ago, hadn't logged on to Zoom for maybe, maybe two weeks. Right. It was around Thanksgiving. And then I was. I was traveling and I had this Zoom meeting, and I open it, I click on the link, you know, a minute before it starts. Because I'm early, I am professional. And of course it starts updating itself because it needed a software update. And I'm frantically texting everybody who I'm supposed to be meeting with, like, blaming Zoom, as if it's Zoom's fault. Oh, of course. Now Zoom decides to do a software update, blah, blah, blah. No, I knew in my heart that this was a me issue. Right, you knew you had a Zoom meeting log on 10 minutes early. Cuz it might need a software update. But that's like how young and old I am simultaneously, right? So old that I'm trying to blame Zoom for a thing that's clearly my issue. And young enough that like, you know, we all had roommates who did dial up porn, because that's what the 90s were like. But as we think about things more and more in a society, if you want to use the word, progresses, we've all thought about AI as well as an actor, of course. Terrifying. The idea that robots and computers could take all of our work. But it's not just actors. No matter what you do for a living, the humanity of your work, the interpersonal skills, the taking pride in your job, even if that means you're in a cubicle all day, whatever it is that you're doing, the fear that maybe technology could replace us is like a real thing. It's not just creepy. It feels like it's getting out of control. And it feels like the heart of the humanity that we all have is being questioned right now. So wanted to have a very interesting guest on who could help us sort through all of that, and that is journalist Jacob Goldstein, who tells me that we've been here before and it started

Jacob Goldstein (Guest, Journalist) (1:41)

in the cloth business. So these original Luddites were like the first people really to be impacted in a significant way by the Industrial Revolution. The first people to face this thing that we are talking about, that we were afraid of essentially losing their jobs to technological change.

Kalpen (Host) (1:58)

In my conversation with Jacob, we're going to go all the way back to the 1800s to the original Luddites, and I want to hear about their story. And we're going to talk about how technology changes, how those changes reshape our work, and then, frankly, who historically gets protected and who gets left behind here

iHeart Podcast Announcer (2:16)

we go again again, again, again.

Kalpen (Host) (2:22)

Hey, I'm Kalpen and this is Here We Go Again, a show that takes today's and headlines and asks, why does history keep repeating itself?

Jacob Goldstein (Guest, Journalist) (12:15)

Yeah, so. So the original Luddites were quite different, just to start, than the word we have today, Right? The word Luddite today means just like somebody who doesn't like technology because they don't like it. Right? So the original Luddites were cloth workers in England in the first part of the 1800s, like 1811, 1812. Around that time and for essentially all of human history, there was very little technological change, Right. This world we live in, where you just assume that technology changes generation after generation, that things get more efficient, that was not the nature of the world until the Industrial Revolution, which started in the second part of the 1700s in England. And it started in the cloth business, right? So these original Luddites were like the first people really to be impacted in a significant way by the Industrial Revolution. The first people to face this thing that we are talking about that we are afraid of essentially losing their jobs to technological change. The cloth business was actually a huge business for England at the time. And the Luddites were skilled artisans. Right. Like, we think of, you know, factory work as terrible in the 1800s, and it was. But before the Industrial Revolution, it was like something you did kind of in your home. It was farmed out. And so, you know, there were all these steps to making fabric, and different people specialized in different parts of it. So the croppers would take a rough piece of fabric and they would have these giant shears, like kind of giant metal scissors, and they would crop the. I guess, the nap. I don't know about fabric. They. They'd crop something off the wall to like, make it smooth and nice. Okay? So that was their job. And for the time, it was a pretty good job. Like, they worked for themselves. They set their own hours. Very poor by the standards of today, which is an important point. But in relative terms, at the time, they were doing well. And then along came the Industrial Revolution, which started out as machines to make cloth, right? So somebody invented a thing to spin raw fiber into thread, and somebody invented a loom. And then somebody invented a shearing frame, Right? A machine to crop. A machine to do what the croppers had done, right? And so this is the thing we are talking about. This is AI taking our job, but for the croppers, but for the skilled cloth makers.

Jacob Goldstein (Guest, Journalist) (15:21)

So these people who have these good jobs, who have these skills, see the machines coming and taking their jobs and they essentially think like, fuck this, like, no, we're not going to do it this way. And so what they start doing is going in the middle of the night and attacking these new machines, like literally physically, like breaking them with sledgehammers. It's like, oh, you're going to do this with the machine? No, I'm going to break your machine with a sledgehammer. And then you can come back to me and I'll keep cropping. And in, I believe it's 1811, it starts to get more organized. So these have been just kind of random ad hoc, kind of what we would call today, like maybe mob might be a word people would use today. But in 1811, it starts to feel more organized and there start to be these letters from this self titled general, General Ned Ludd. And he's actually holed up in Sherwood Forest like Robin Hood, who has kind of similar vibes, right? And these letters are taking on the tones of civil war, frankly, right? He has this title, General Ned Ludd. And at one point they call his army of Redressers, right? Like a redress of grievances. The main thing you need to know about Ned Ludd is there was no Ned Ludd. He was. He was a myth. He was a myth. He was like Robin Hood. He was like Robin Hood. I mean, there may actually have been a guy named Ned Ludd decades earlier who was like a frame breaker. But like this General Ned Ludd, this guy leading the revolt, he was an invention which is kind of genius, right? Like, it's a genius way for a people with no political power, for a group of people with no political power, to like create a movement, right? You invent a figurehead, a mythical general holed up in the forest who does not exist. And so it's this idea that the Workers are not just randomly breaking machines. They're organizing to fight back. And one thing that's interesting, there's this historian who has called what they were doing collective bargaining by riot because there were no unions. Like they couldn't even vote. Right. There wasn't a mass suffrage in, in England at the time. There were certainly no unions. They basically didn't have power in any organized way. So they were seizing power. And it's this collective kind of ad hoc way. And these attacks get more systematic. There's this one particularly dramatic one where these guys, they all mass at this bar and they're going to attack this mill. But the mill owner knows, like the Luddites attack, you know, have been attacking around this region. He's been preparing to defend himself. So the owner is actually like sleeping there. He's hired some people with rifles to defend the factory. He actually has like a vat of, I think sulfuric acid. He's going to like pour down on them. Yeah, it's very medieval, right? It feels very like medieval castle. He's made this factory like a fortress. And so the Luddites march on it. It is, it is very, is like proto civil war, right? This is an armed, organized attack on a heavily defended factory. And they get in and there's like actually an exchange of gunfire and ultimately they retreat. So there's two Luddites dead. They have failed in their attack. And around this time, Parliament, you know, the British government realizes that this is getting out of hand. And they have passed a law making attacking machines punishable by death.

Jacob Goldstein (Guest, Journalist) (37:08)

That's super hard. I mean, you know the. I think the closest thing in recent times that comes to my mind is workers who've lost their job to foreign competition. Right. Like in the kind of early part of the arts, there was what's come to be called the China shock, which was China entered the World Trade organization in like 2000. It's funny, not that long ago, right? China used to be a super poor country, was not a major competitor. And then bam, they entered the wto and there were places in the United States that were making things that competed with Chinese imports, like clothes, and they got obliterated. The United States as a whole did well. And I mean, ordinary people, right? Like it is the case that like, for working people, when clothes get cheaper, that is good, right? It means they have more money in their pocket, more money to spend on basic things. And I think it's easy to overlook that part. But the, the people and the towns that were competing against China were worse off, right? So overall everybody was better off. And it's important to say that, like, it wasn't just rich people who got better off. It wasn't just the owners of capital. Right? And I think that is likely to be true here as well. Right. It is a competitive world and I do think that there is a universe where overall people are better off from AI. The really hard question is, how do you help people who are clearly losing their jobs because of AI, Right? Like, well, give them money seems like a good part of an answer to me. Will it happen politically? I don't know for the reasons you said. But if I were waving a wand, give them money. In a way though, it seems like I don't want to say the easy part because it would be great if it happened politically, it would be hard. But there is this more complicated thing for everyone, right? And Keynes talked about it 100 years ago. It's like work is meaning for a lot of people, right? Work is purpose. Work is just an organizing principle in life. And so if we project forward, I don't know what's going to happen. I don't think all jobs are going to be gone in five years. Maybe I'll be wrong, but I doubt that. But if in fact lots of people are losing their jobs because of AI, yes, please give them money. Of course there will be more money to go around. There should be money for those people. But like, what do we do about everything else? How do we, like, help them find meaning in their life? It feels hand wavy to me, but like, might be my own problem in three years, right? Like, my identity is my work to some significant degree. And like, technology might put me out of a job in a way it's easier for me to talk about now that it's me. I don't just sound like some asshole talking about other people in a condescending way. Like, this is me. Like, truly, I could put me out of a job before I want to be out of a job. And like, it will be hard in many ways if that happens, not just the money.

Jacob Goldstein (Guest, Journalist) (44:25)

So I guess what still worries me when I look ahead is the rate of change of AI. Because when you look at these instances and the alternatives, right, so like the Luddites are this very dramatic story where these people who had a decent life lost their jobs to machines and their lives got worse on a much vaster scale was the automation of farm work, right? That was like almost everybody worked on a farm and then almost nobody works on a farm now. But there wasn't really. I mean, you know, farmers organized politically in various ways and they wanted different policies, but you never had a kind of Luddite moment for farmers, in part because it was gradual, in part because you had industrialization alongside it, so people could leave the farms and go work in a factory. So if it's really sudden, if a huge amount of people lose their jobs really fast, that just feels super politically dangerous and unstable. Right. Like, it could be violent, it could be bad. I mean, the hopeful thing fundamentally to me is that people have been worried about technological unemployment for 200 years and indeed pockets of people have really suffered from it for long periods of time. But today, the employment to population ratio, the share of working age people with jobs, is like as high as it has ever been. Right. Much higher than it was 50 years ago when far fewer women were working despite incredible amounts of innovation, technological change, technological job loss. So I think we really do underrate the extent to which we are good at coming up with new jobs. Jobs we cannot imagine today. And like, I actually think that'll happen in the long run. It'll be maybe embodied things, you know, like maybe I'll go, I don't know, be a meditation instructor or something. And yes, you could have AI be a meditation instructor. But there are some things I think people who will be richer overall will pay for a human being to do. I just don't know what those things will be.