
American Socrates
Think Deeper. Live Better.
Tired of shallow takes and surface-level answers? American Socrates helps you cut through the noise and see the world more clearly. This is a podcast for anyone who wants to think for themselves, challenge assumptions, and live a more intentional, meaningful life. Host Charles M. Rupert brings the power of critical thinking and timeless philosophical insight into everyday questions—like how to find purpose, make good decisions, grow as a person, and navigate a world full of misinformation and confusion.
From art to relationships, social justice to success at work, no topic is off-limits. This isn’t a lecture on famous philosophers. It’s a wake-up call for your mind.
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American Socrates
What Does Working-class Freedom Look Like?
Jake got out of the military expecting freedom. What he found instead was gig work, debt, and a life lived at the mercy of corporate algorithms. In this episode, we follow Jake’s journey—not just through the quiet desperation of techno-feudal capitalism, but toward a vision of what could be. What if rent didn’t rule your life? What if income was guaranteed—not earned through suffering, but given as a right? What if ownership was shared, not hoarded?
This episode imagines a bold left-wing alternative—not just to the neo-feudalism of the right, but to capitalism itself. Through narrative, glimpses of real-world models, and emotional reflection, we offer something rare in political media: not critique, but a dream worth building.
Jake thought he was a free man. I mean, he'd finished his three-year enlistment in the military. He had gotten out clean; he was honorably discharged. He was done being told what to do. No one telling him when to wake up, what to wear, what to eat, where to be, and when to be there. He was going to set his own schedule from now on. Well, sort of. He didn't want to have a boss. He didn't want to have a time clock. Isn't that what freedom means? At least that's what everyone told him.You serve your country, you learn some skills, you get support when you come home. Fortunately for Jake, when he got back to Ohio, many of the programs that were supposed to support him while he transitioned back to civilian life, were being gutted. The job training program that he had enrolled in vanished in the latest round of budget cuts. The benefits, especially his health insurance, were delayed, denied, and then disappeared. Now Jake's working delivery. Some days, he works ride shares, some days he delivers food, but he doesn't own his car. He just leases it through the gig company. He still has no health insurance, no savings, no real plan for the future. And still, he tells himself he's free. Technically, he can quit. He could start his own business or move to a different city or just do something else. He wants to own his own food truck. Yep. Jake tells himself he's free every single morning, but you and I both know that he's not, and so does Jake. You see, oppression doesn't just have to come in the form of iron chains or overt laws. It can come feeling just like freedom, and that's what makes it so dangerous, because you don't know that you're being oppressed. It feels like freedom, but it's actually control. Last week, I raised the idea that a dominant narrative on the right involves moving past capitalism into what I was calling technological neofeudalism. In this episode, I want to explain that a little more and propose a sort of left-wing counter idea. I want to imagine a different future for us, a better one, I think, for working people, for struggling families, for the folks holding this country up day after day with tired backs, frayed nerves, basically for my people. Because the visual we're being offered right now, the one that's coming out of Silicon Valley billionaires and right-wing intellectuals, and influencers who sound like they care about suffering, but really just want obedience, is the new kind of feudalism. This is where language is freedom, but the structure itself is actually control, which is, in my estimation, a pretty good working definition for oppression. That's what oppression feels like. That's what it looks like. It sounds like it's offering you a bunch of choices. When in reality, those choices were highly limited from the beginning, and you simply get to choose among the ones that someone else had already selected. That's the future I fear we are heading towards, if we don't imagine something better than capitalism here on the left. So that's what I'm going to do today. I'm going to do this by telling a story about a man you've already met him named Jake, and the invisible cage that he's now trying to escape. Along the way, we're going to ask some simple but dangerous questions, the chief of which is, what if we don't have to live like this? Jake is 27. He's white, he's working class. He grew up in a family in Ohio. He joined the army at 20, partly out of patriotism and partly out of desperation. He left the service after five years. He liked the promise of it, the structure, the skills, maybe college down the line, and support if he needed it. But when he came home, the landscape had changed, and the safety net that he thought he had suffered some pretty significant holes. So Jake did what a lot of people do. He signed up for the Reshare Act, then a delivery app, and now he juggles both, plus, you know, the occasional task rabbit gig. He's always driving, he's always hustling, just trying to stay ahead of his bills. Jake is the working poor. He's a pauper. He works full-time, more than full-time in most weeks, but he still can't make ends meet, let alone save up any money for something else. And it's not like he lives extravagantly. He has a tiny, shared rental that he hates, but he really can't afford to leave it. It's overpriced, moldy, and the landlord barely returns his car. Oh, and if he does, it's only to tell him that his rent's going up next month. And moving costs a lot. And Jake doesn't have that kind of money. Yeah, he'd love to buy a home, just like everybody else. But that's not even a dream for him anymore. It's withered, like a raisin in the sun. He tried, but the down payment, the credit score, the hoops that he'd have to jump through, they just were not built for people like him. And he didn't serve long enough to even qualify for the VA Home loan assistance program. He owns nothing. Every asset is someone else's income stream. And when something breaks in his life, his car, his health, his phone, he takes out short-term loans with loan shark-like rates, just to stay afloat. Keep working. Jake exists in an invisible cage, because it's invisible, Jake and everyone he knows thinks of him as free. But every path forward has already been shaped by somebody else's hand, by corporate policies, by budget cuts, by algorithm tweaks, by court decisions, by statutory laws. These decisions were made far above him, and in many cases, long before he was even born. Jacob is oppressed. He feels the weight of it, but he can't recognize it because he's not black or a woman or a gay man. He's not an immigrant or a native. He's not disabled. He's not anything except poor in a capitalist country. Capitalism doesn't work for Jake, and he doesn't know what to do about it. Now, enter the techno bros and their modern right-wing solution to all of this, this neofeudalism. If you just empower me to rule over you, Jake, I'll make a place for you in my new order. I'll restore you the dignity that was once belonged to your grandfather or great-grandfather. In the old days, peasants were legally bound to the land, meaning that whomever held the land, the serfs, as they were known, became a part of the package, right? The land could chain the hands, but the serfs stayed with the land. They had to work the land, but they couldn't be removed from it. They couldn't be fired from their position. They farmed for their Lord, and they prayed to God for rain. They paid the Lord a percentage of the produce that they generated, and they got to keep the rest. They could either eat it or sell it at the market for their own profit, something like that. And In a sense, they're freer than Jake, because they were assured access to the land, to farm, and to have a house to live in. Generation after generation, these serfs knew that they could stay in this place, and they could live this life. And there's an essence of economic security in serfdom and feudalism. Jake's not bound by law to any kind of job, and hence his economic insecurity that ultimately oppresses him. That's the result of the freedom of capitalism, you know, freedom and scare quotes here. It's one Jake longs to escape from. This new feudalism promises just that. Jake's not going to be tied to the land, of course, but he will be tied to some sort of technocorporate overlord. He will not be bound by the law. He's going to be bound instead by economic necessity. He will not pray to God for rain, but he will pray to the algorithm that he gets a night full of ride shares so that he can make money. And maybe the most heartbreaking aspect of all of this is that Jake blames himself for his problems, for not figuring out how to succeed in society, maybe not working hard enough, for not being able to climb higher, for falling behind. There's an appeal, then, self-preservation instinct in him that pushes Jake towards things like sexism and racism. Maybe he could say that, well, DEI is the reason he's not successful. If those people just stayed in their place, they wouldn't take my job that I'm better qualified for, then there would be room for me in this economic table. And so really, it's this progressive egalitarianism that is the problem. Jake's isn't some one-in-a-million story here either. Jake is everywhere. He is the guy who's delivering your groceries. He's the guy who's bringing you your McDonald's order. He's the guy who delivers your Amazon packages. He's the guy you call to fix your sink. He's the guy who bags your groceries. He's the guy who's selling you your next cell phone. Jake's tired. Jake's stuck. And Jake is wondering what the hell went wrong. So let's start with the simple truth. Jake didn't fail. The system failed Jake. And if we can see that, I mean, really see it. We can start to imagine something better than isn't some sort of techno feudalism and the classism, sexism, and racism that are required in order to support a system like that. You know, what Jake really needs to set him free? Ownership. I know that it's probably not what you're thinking, from a left-wing alternative to capitalism or something that I would suggest. But that's the answer all the same. Jake doesn't need stocks or real estate. That's going to be out of reach for him anyway, but he does need his own business, a hustle that he can actually call his own. Something where people don't take a percentage of what he does. Something honest, something practical. You know, he's always been good with his hands, so what if he started a mobile car repair service? Low overhead, flexible hours, growing need? Seems like a solid bet. Now, maybe Jake watches some YouTube tutorials on drafting a business plan. Maybe he even took a few free online courses at his local library. He made a logo, he found a cheap van on Facebook Marketplace. But dreams need fuel. And in this country, fuel means credit. So maybe Jake applies for a small business loan, and what he'll get is a crash course and find financial feudalism. The terms of this loan are going to be brutal. They're going to have high interests. They're going to have short repayment windows. They're going to have hidden fees that multiply, like weekseds, if anything, and I mean anything, doesn't go quite to plan. But what choice does he have? He'll either take the loan, and that'll be that. Or he's going to work for somebody else. If he takes the loan, he's going to find out Jake still has a new boss, not a person, but a payment schedule. Every job he picks up, every oil change, every brake pad he replaces. Before he can pay himself, he has to pay them. And then there's gas, there's the suppliers, there's the insurance. And, of course, he's still paying rent. Even as a business owner, Jake wouldn't own where he ultimately lives. That check will go straight to his landlord, who's never going to lift a f finger, but he's going to make more than Jake does by breaking his back, working at this business. It wouldn't take long before Jake started to notice something strange. His name might be on the business, for sure, but his time, his money, his energy, all that belongs to other people, just as assuredly as if he were their employee. Jake's not going to be able to escape this way. He's just going to jump from one kind of cage to another. Don't get me wrong. He's going to do better this way, but it's not ultimately an escape. He will not be able to lay down his burdens. When he stops being able to work, he will stop being able to make money. OK, let's zoom out a little bit here. Jake's story is a blueprint. The system we're living in has sold us a lie. It's an old lie, but maybe with a new rapper. The lie is that if you work hard enough, hustles smart enough, own just one thing, be it a business, a car, a dream, you'll be free. But under capitalism, ownership doesn't mean freedom. It means risk. It means debt. It means taking on all the responsibility, but not necessarily all of the power or all of the income. Some of the aspects of old feudalism remain in capitalism, like landlordism. Neofeudalism is hoping to expand on those aspects, to remove democracy and restore hierarchy, to save us from capitalism. Company towns once gave workers a place to live and a place to work, and in exchange, they took every cent that that person made. There's no quibbling about it. It's a kind of slavery, where you ultimately do all the work, and your master makes sure that you're able to continue working. Nowadays, we call those company towns live, work, play communities, or even worse, smart cities. We used to have public town centers, and now we have private shopping centers. This isn't yours anymore. And you can't go there and speak your mind in the public square. Instead, you go to the mall and you will be removed by mall security if you disrupt commerce. Amazon builds the warehouse, then the apartment. Then they buy the grocery store. Then they sell you your surveillance doorbell, and suddenly, your entire life, your job, your rent, your food, your security. It's not a single platform. It's under a single brand. That's not innovation. That's the new enclosure. It's the same strategy feudal Lords used 800 years ago, just with better marketing, I guess. Jake can't escape this, not by working for himself, not by working for someone else, either. His only hope is to do something completely different. So Jake's world has been a grind. It's this relentless cycle of gig work, mounting debts, and elusive dreams of stability. But let's put him somewhere new and see how things could look different. This new world would look pretty much just like ours. There are still families in it. People still live in houses. They shop at grocery stores. They go to church. They watch football on the weekends. People still go to work. They still make money. They carry around in their wallets and spend it on things like that they want and need. None of that's going to change. It's hard at first even to notice what the real difference is going to be. But as you look at this new world, you begin to notice there is a pleasantness everywhere. Maybe the people are just a little friendlier. They seem less anxious, less scared, less angry. There aren't any homeless people. Everyone seems like they're doing okay. Jake seems happy. He's got his food truck. He owns it. He makes sandwiches for hungry workers at a nearby tire factory. So what changed? What could we do to bring about that world? There are two simple things that we would need to change. The first is the abolition of rent, or you're taking away people's ability to make money simply through owning things, you know, not through their labor, but by simply owning something. be it shares, be it a house that they rent out or a loan that they draft an interest from? Owning should not be enough to draw any kind of income in our world. You have to work for a living, which at the same time requires that workers own the businesses and the capital that employs them. Models of this, like community land trusts, local credit unions, and tenant or worker co-ops, already exist under capitalist constraints, which is kind of a minor miracle. With all the pressures capitalism puts on these businesses, they're still able to run and operate a successful business, even without the kind of investment, incentives, and models that corporations use under capitalism. Imagine how much better they would be able to work if all businesses had to operate on that same model. There would be no investors in a business because you would have no way to make money off of it through investment. The only way you could make money through a business is by working at the business and generating income through the business. They might provide limited, but useful examples of what this world would look like, but the real power of the change can't be realized in this piecemeal way. It would come only from the idea that no one can be exploited. Nobody can work and have a portion of their income taken away from them. That's just not an option anymore, ever. The other change is the guaranteed income. You can retire, get injured, have a baby, or maybe even just drift for a little while without completely losing everything you possess in life. I'm not saying your money would be great and you would be living well doing this. You're not going to make as much as you would by working. But in this world, no one falls off the bottom rung in the ladder. This would provide people with time and stability and the freedom, then, that they would need to develop themselves into who they really want to be, instead of being forced to be tools for some kind of master in a great hierarchy of control and domination. And that's it. These two ideas sound simple, and they really are. They wouldn't be hard to institute. They wouldn't be hard to put in place. A simple law saying that you can't make money from your money should be sufficient. And the establishment of a guaranteed income would be more complex and there are different models for a universal basic income. And we could talk all day long about which one of those is the best. But some sort of system would need to be in place. Otherwise, you would find that you have a similar problem to Jake's, in which you stop working and you stop being able to support yourself. This would cause a kind of desperation where people would work, take jobs that they don't want, that they don't like, just to be able to make a living, which means that they would be able to accept lower wages than they would otherwise accept. You can think of this, you know, universal basic income as making a backstop on how low wages can get. People would enter into businesses, even as part owners, where they wouldn't necessarily, the other people who worked in the business wouldn't necessarily want them to make as much money as possible, because that gives them a larger share of whatever the business generates. So there would still be pressure to push wages down. But these people would then have to hire them at a wage that was comparable enough to entice people to come and work for them, or they would have to figure out a way to do the work without them. In my own thinking, the ideal form of guaranteed income would be pegged somehow to a, you know, per capita of the GDP. This would allow the amounts you receive to vary depending on how well the country is doing. When times are good and the country's being productive, the amount of money you could get from not working would be high. And so people would retire, people would, you know, take the time off. On the other hand, that would slow productivity. The amount would go down. And so people would naturally have to go back to work because they're not able to purchase. Like it would work in two ways. You would get less money from this guaranteed income, while at the same time, the prices of everything on the market would go up. So you'd be bringing in less money while things are getting more expensive. Eventually, I imagine this would find its optimal point. There would be equality in the sense that there would be a certain amount of people working, a certain amount of people not working, and it wouldn't actually vary up and down wildly. My, to be honest, what I imagined would happen is something like, you know, people would work from the age of 20 to the age of 40 and that would be it. Most people would retire by the age of 40. So you'd spend 20 years of your life working and making an income, and then you would retire on whatever it was because you'd have things like you'd own your house, you'd own your car, you'd have plenty of money in reserve to take vacations and do other things that you wanted. And you could just live on what your society provides to you. You provided for your society for 20 years, and now other people provide for you, and the system just continues on and endlessly like that. So let's take Jake, for example. In this world, Jake could go to school until he was 20, maybe still enlist in the military and do that for five years, then come out and take a job doing something else somewhere else, perhaps as an auto mechanic, do that for so many years. And if he really enjoys his job, you know, starting his own business and working a food truck, he might do that for the rest of his life. Nothing says he has to retire. If he enjoys running a food truck, he can just do that. He could even hire other people, but those people have to be invested in his food truck business. They're not his employees. They would become his business partners. Right? They would get a share of the profit. Of course, they also have to invest. If he owns a bunch of capital in the business, they would have to invest in that capital as well, meaning they would have to pay Jake back for their share of the capital. If I own 100% of the business and you join me, you have to purchase 50% of the capital in the business, and you can do that through labor if you don't have the money right up front. You know, we could take a chunk out of every paycheck. They would be your money going to me to pay me back for the capital. Of course, if you retire, then the business has to pay you back out, right? If we sell off the capital and you own 50% of it at this point, you're going to have to get 50% of whatever we sell it for. In this way, it sort of has its own built-in retirement plan. This isn't to say that this system would be entirely utopian. This is not going to solve all of our problems. We will still have things like sexism, racism, and perhaps even classism. There will be different issues, but what I'd like to think would happen is that that a lot of those would get toned down. It's not so desperate if someone calls you a name when it doesn't affect your ability to make money. If you're doing just fine, economically, people can call you names all day long. It's not going to bother you. It's when those names also have an impact on your job prospects that they become very damning.. They're real world, real concrete damage that can be done. We would still have issues in finance. We would have issues of trying to figure out who to give loans to, how to help people purchase houses when they're starting with nothing, things like that. But all of those are easily overcomeable with just the most minor of innovations. You do not have to be a financial wizard to figure out how to solve those kinds of problems. You know, Jake hasn't made it there yet. And nor will he be able to make it to this place on his own, because these problems are ultimately structural. They are baked into the system that we built. Currently, he's still driving. He's still renting. He's still watching his paychecks vanish before the week's even done. But now, he might have a vision of something that's different. And a vision once seen is hard to unsee. Emerson said, "A mind once stretched by a new idea never returns to its original dimensions." Jake saw a world where literally everyone owned their homes, not just rented their future. He saw people with time on their hands, and not just tasks that needed to be done for money. He sold dignity that didn't just come from setting yourself on fire to keep your superiors warm, but from being human in a community that honors that. And yeah, that shook him, because it wasn't some utopian fantasy. It's a real possibility. And the only thing that's lacking here is the will to make it manifest. It's already happening in places, right now, in pockets, in places that you just don't see on the news. People are organizing, building housing that no one can flip for a profit, running worker-owned businesses, fighting for guaranteed incomes, not as charity, but as a foundation for freedom. And so my call to action for this episode is simple. Are you not Jake? What would your life look like if you didn't have to hustle every minute just to breathe? If your rent didn't eat your dreams, if quitting a toxic job didn't mean risking everything. If you didn't have to choose between paying the bills and getting your medicine. If being free didn't come at the price of everything you do and everything you are. This isn't about politics. It's about power, who has it and who doesn't. And it's about building a world where more of us have a real say in what happens. The right wants you to think that there's no alternative to the bloodbath of capitalism other than their neo-feudalist system, that the only options are to surrender to their masters or perish. Obey or be irrelevant. But that's not true. We don't have to accept serfdom wrapped in gig economy freedom. We don't have to work ourselves to death to make someone else rich. We can build something better. The question isn't whether we can afford this future. The question is whether we can survive anything less. So I leave you with this. Can you see yourself in this brave new world or not? Thanks for tuning in to American Socrates. If today's episode of philosophy got you thinking in new ways, make sure to subscribe so you'll never miss an episode. New, full episodes drop every Wednesday. If you enjoyed the show, leave a review. It helps others find us and it means a lot. And if you know someone who could use a little more practical wisdom in their life, share the episode with them. Want more? Visit AmericanSocrates.buzzsprout.com for show notes, resources, and exclusive content. You can also follow me on Facebook, Blue, or TikTok to keep the conversation going. Until next time, keep questioning everything.