Today’s wrong question is: “Does everybody need to become an entrepreneur?”
There’s a big undercurrent of this kind of message right now. Really smart folks saying the era of stable employment is over, the future belongs to the builders, go start something, best time in history to be an entrepreneur, blah blah blah.
Some version of that is… true.
I’m not going to sit here and tell you the future of work looks like the past, or the present. It doesn’t. We’ve talked many times about why A.I. is real, why the disruption is real, and why the unbundling of jobs into tasks is real.
But here’s what’s also real, especially in the United States: your job isn’t just a job. Your health insurance is attached to your job. Your retirement savings is attached to your job. Your parental leave is attached to your job. Your paid time off, your disability coverage, your unemployment paycheck… all of it, attached to a full time job.
So when someone says “the era of stable employment is over” — in the U.S., what they’re actually saying, whether they mean to or not, is: the era of a stable social contract is over.
And that is a conversation I’m just not hearing. So we’re going to have it today.
The Stupidest Social Contract
Did you know the U.S. is the only developed country in the entire world where losing your job also means losing your healthcare?
Seriously.
Brings a new meaning to “American Exceptionalism,” doesn’t it.
No other developed country on earth looks at the thing that keeps you alive and says, “Yeah, we should run all that through your boss.”
I hope we can agree: that’s a remarkably, almost unbelievably, stupid idea, even though in the U.S., it’s the most “normal” thing in the world.
But did you know this arrangement happened mostly by accident? Here’s how.
During World War II, the government froze wages. Companies couldn’t compete for workers with bigger paychecks, so they started offering health insurance instead. The government said “thumbs up,” and even added tax benefits for employers and employees.
Then the war ended. The wage freeze lifted, but the tax break stayed. So companies kept doing it — not because it was the “right” system, but because it was cheaper than paying equivalent wages. Incentives! And, because, let’s be honest… if your healthcare is attached to your job, you’re a lot less likely to quit.
“Congratulations, here’s your leash, sir.”
And the kicker is: nobody really “designed” this. A wartime accounting rule became a tax loophole which became corporate retention which became… the foundation of the American social contract.
I call this kind of nonsense a “frankensystem” — a janky, pieced together system-like-thing that’s awkward as hell and is frightening to look at.
For the last eighty years, the U.S. has built its entire social safety net on this rickety foundation — not as a public system, like the rest of the developed world, but as a private system, delivered through your employer. You want healthcare? Get a job. You want retirement security? Get a job. You want to be able to afford your bills when you have a baby? Get a job… maybe. Better hope it’s a good job that likes babies. And make sure you don’t tell them you like babies before they hire you… it’s a whole thing.
The W-2 i.e. Full Time Employment i.e. FTE became the U.S. delivery mechanism for a functioning social contract. I’m going to use those three terms interchangeably in this episode, by the way.
And remember: the U.S. is completely and utterly alone in the world in doing things this way.
To make our social contract worse, let’s bring in neoliberalism. If you caught the episode two weeks ago, you know this is the ideology nobody admits to liking but has somehow has still ruled the last almost-50 years of our economy.
Starting in the late 1970s and accelerating through the 80s and 90s, the dominant economic logic became: markets are efficient, government is not, privatize everything, deregulate everything, and just trust that the “invisible hand” will sort it out. Right? You’re familiar with this playbook. This is the world of my entire life.
One of the quieter effects of this era was a systematic weakening of the institutions that could have provided some alternatives to this employer-based social contract.
Unions might have helped, but they were being actively undermined by Reagan (and others). Private pensions could have helped but were quietly replaced by 401(k)s. Public housing was deliberately stigmatized and then demolished, leaving the market to “solve shelter” for working people. And a LOT of propaganda — including the creative use of some powerful bogeyman “-isms” like “socialism” — helped ensure universal healthcare never got traction in the U.S. (you might notice some of this is still happening right now, today).
The logic was, and in many ways, still is: the market will handle it. Your employer will handle it. You’ll be fine.
But… my friends, we are clearly not fine.
Look around… I don’t think I know anyone that feels like things are “fine.”
To me, it seems clear: the invisible hand is giving us the invisible middle finger.
“Coase’s Law Is Now Dead”
Almost a hundred years ago, an economist named Ronald Coase wrote a paper asking a deceptively simple question: “Why do companies exist?”
Like, really… why?
In a market economy, theoretically, you could just contract everything out. Hire a freelancer for this, a specialist for that, negotiate every transaction separately. Why bundle all of that into a single organization with employees in the first place?
His answer: because transaction costs inside an organization are cheaper than outside it. Managing, coordinating, and trusting people you’ve hired to be there all the time is ultimately less expensive than renegotiating every task with a new contractor every time. So we bundle. We build firms. We create employers. And employees.
Coase’s insight basically explains the entire architecture of the modern corporation. Companies exist because coordination is expensive, and centralization makes it cheaper.
But A.I. seems poised to destroy this logic.
If A.I. agents can coordinate workflows, manage communications, handle back-end logistics, and string tasks together automatically, the complex transaction costs that justify a “company” collapse.
Peter Diamandis, entrepreneur and futurist, recently called this “the organizational singularity.” He argues that one person with A.I. can now outcompete a traditional firm with dozens of employees. That companies will shrink to a fraction of their current size while solo operators run entire operations. He even cites Coase directly, in a “I’m reporting on a murder” way, basically saying: “Coase’s Law is now dead. You must become an entrepreneur… now!”
This might be directionally-correct (I largely think it is), but here’s what Diamandis, and everyone I hear making this kind of argument, just breeze right past: in the U.S., a company isn’t just an “economic coordination unit.”
It’s the delivery vehicle for our social contract.
If, or probably when, “Coase’s Law” dies, my friends, the W-2/FTE arrangement will die with it.
This is what we ought to call a “big-ass problem,” because the W-2 was never just a paycheck. It’s also a bunch of other stuff that makes your whole life work.
What The W-2 Was Actually Doing
At this point, all my U.S.-based entrepreneur friends listening to this are nodding like, “Yeah, duh, Josh.” Because I’m basically describing the reasons why being an entrepreneur really frickin’ sucks.
We entrepreneurs have always had to like, jerry-rig some kind of social infrastructure around ourselves like a Rube Goldberg machine. We’ve always had to pay out the nose for health insurance that covers mostly nothing and pray to the gods of Pfizer that we won’t ever need a prescription for anything. No one has ever “matched” our retirement or paid us to take time off. We don’t get paid every two weeks; in fact, it’s perfectly legal for Gigantic McCorporation to hold our money for two full months after we complete work before paying us! (It’s called Net60, and it should be illegal for large companies to use on small businesses, but it’s not.)
But all that said, I’m quite certain we have folks listening to this who have primarily had Full Time Employment roles their whole lives. This episode is really for you. Y’all need to hear this, because it’s really, really important.
That invisible middle finger I mentioned a moment ago is actually aimed at YOU.
Companies have been quietly dismantling the FTE structure for a while. And I bet you’ve seen it… there’s just a lot more going on than you might have realized.
You’ve probably noticed Uber, Lyft, and DoorDash… they didn’t build “workforces,” they built “platforms,” which legally meant their drivers weren’t employees, but “independent contractors.” No health insurance, no sick days, and no unemployment.
The companies called it flexibility. Workers called it… other names.
If you’re in a Full Time Employment situation, I think it’s easy to write that off as a “gig economy” problem that doesn’t really impact you.
But it shows the larger direction of all this.
What you probably haven’t noticed is that some of our largest, most prestigious, most profitable companies have been running a very similar playbook… inside their corporate offices.
Did you know in 2019 Google reportedly had more contractors than Full Time Employees? 121,000 contractors working alongside 102,000 FTEs. Same offices, similar jobs, but very different agreements. Contractors got no health insurance, no job security, no seat at the table. A shadow workforce, hiding in plain sight.
From my research, it seems like Google wasn’t an outlier as much as a typical scenario.
The actual numbers are incredibly hard to pin down — which makes sense as this is a PR nightmare waiting to happen and companies don’t have to disclose this kind of information — but we can piece together what’s happening through various employee misclassification suits against companies like Amazon, Ritz-Carlton, and Costco.
I’m pretty sure this is just the tip of the iceberg, y’all.
But I don’t think there’s any kind of mystery or conspiracy here, just incentives: companies are incentivized to increase capital, so that’s what they do.
FTEs are very expensive; when we account for so-called “benefit” costs, those people cost about 30% more than contractors. Multiply that across a payroll of hundreds or thousands or hundreds of thousands and you don’t need an “evil genius plan” to figure out why companies are trying to avoid that cost.
But this isn’t all companies do to save money. When companies aren’t “optimizing costs” through employee classification, they’re just straight up taking away “benefits” from FTEs directly.
Just last week, Deloitte — one of the most prestigious employers in the world, a firm that reported $70 billion in revenue last year, up 5% — announced it’s cutting parental leave in half for a segment of its workforce. From 16 weeks to 8. How much adorable baby time do you need? (8 weeks. The answer is 8 weeks.) They’re also eliminating pension accruals, cutting paid time off by up to 10 days, and scrapping fertility assistance and adoption reimbursement. Take note: this is a company that apparently doesn’t like babies.
Their revenue is growing. But their cuts are accelerating. Why? A professor at Wharton explained it with remarkable candor: because “With the job market slack, they feel they can.”
That’s it. That’s the whole thing.
Here in the U.S., we use a peculiar word to describe these services offered to employees: “benefits.” I just used it a couple times. I’ve always found this word a bit odd, but it’s all making sense to me now. These aren’t rights, and they never were. They’re not seen as things humans need. They’re a “benefit,” which means they are gifts that can be returned to the giver. Not because companies are struggling. But because the power balance has shifted, and companies are taking what the moment allows.
Now let’s zoom out.
Deloitte is doing this before the full wave of A.I.-driven workforce restructuring hits.
This is just the preview, my friends.
The actual “Feature Presentation” — when firms shrink to 20% of their current size, when the gig model extends into white-collar work, when “Congratulations, you’re a contractor now!” becomes standard — that’s when the W-2 erosion goes from “trend” to “new normal.”
I want you to notice: A.I. isn’t creating this dynamic, A.I. is just going to remove the last reason companies had to hire you full-time in the first place.
Bye-Bye Health Insurance
What happens when you lose full time employment in the U.S.?
As mentioned, there’s a whole litany of “social contract” items that come with Full Time Employment that often go unnoticed (if you’re an FTE): retirement savings, paid time off, parental leave, regular paychecks, quick paychecks, HR departments, support and resource groups, unemployment pay, and so on.
But the biggest one, of course, is health insurance. Or as people in other parts of the world call it… just kidding, they don’t call it anything! They don’t have this abomination in other parts of the world! Nobody else has this kind of mechanism for covering basic healthcare.
U.S. health insurance itself could be a whole episode, but for now let’s take a brief look at the numbers.
About 164 million Americans get health insurance through an employer. This is the W-2/FTE system working as designed. This is about half of us.
Another 120 million are on Medicare or Medicaid — elderly, disabled, or low-income enough to qualify. Keep in mind when I say “low income” I mean LOW — the number varies by state, but as an example, to qualify for this in Colorado in 2026 a single working-age person must earn under $1769 a month. That’s $21k a year. Can you live on that? This is about 36% of the U.S.
Then, about 35 million are utilizing what we call the “Affordable Care Act” (ACA/Obamacare) Marketplace or direct-purchase plans. These are the self-employed, the small business owners, the freelancers, paying out their ears for the privilege of figuring it out themselves. This is 10% of us.
About 27 million Americans have no coverage at all. This is about 8% of us.
But there’s another number that doesn’t really get talked about: 23% of our working-age adults are underinsured. If we include the uninsured in this figure, that’s between 60-70 million people. What does “underinsured” mean? It means we have some kind of coverage, technically, but we still don’t have affordable access to care.
I am one of these people.
Just last month my plan was up, so I shopped extensively because I hate the plan I was on (it cost me a fortune last year). After all my shopping I found the best plan available to me as a self-employed person was… the crap plan I had. I pay a hefty premium every month, and I’ll be writing a $7,000 check later this year for a medically necessary surgery. Remember, this is with insurance.
I shopped around. A lot. I did the math. This was my best option.
I am incredibly fortunate. Knowing this is coming, I should be able to budget for this and make it work. Far too many people are not this privileged.
Add all of this up and we’ve got a system where almost all of us in the U.S. are either one job loss away from a healthcare crisis, or we’re already in some version of one. Medical debt contributes in some way to two-thirds of bankruptcy filings here. And remember, “medical debt” is a concept other developed countries wouldn’t even comprehend.
And now we’re about to dramatically accelerate the dissolution of the Full Time Employment social contract that makes all of this mostly livable for the rest of us.
Why are we not connecting these dots??
The entire architecture of U.S. healthcare access is built on the assumption that most adults have a full time employer. What happens to that architecture when the employment relationship becomes optional, fluid, short-term, or just… gone?
I am not hearing any good answers to this yet.
And if the trend continues in the direction I think it will, I’m afraid a whole lot of my W-2/FTE friends listening to this are soon going to be living on the entrepreneur side of the social contract line.
Let me tell you something: you aren’t going to like it.
There’s a lot of great things about being an entrepreneur in the U.S. This is not one of them.
What We Need: The Commons
So if the W-2 is the delivery mechanism for the U.S. social contract, and A.I. is killing the W-2… what replaces it?
The problem, at its core, is this: we’ve been running two fundamentally different kinds of things through the same system — The Market — and pretending that made sense. It doesn’t.
The Market is genuinely extraordinary at certain things. Novelty. Competition. Variety. Driving down costs through innovation. Making weird snacks at Trader Joe’s. All of that is great.
But The Market has one prime directive: maximize capital. That’s just what the system is built to do. And it works fine for certain things… things we don’t NEED.
The Market works terribly — catastrophically, actually — for things we need to survive. Housing. Childcare. Clean water. Education. Energy. Healthcare. The things where, if The Market decides you can’t afford it, you just… don’t get it. And then you die, or your kids don’t learn, or you stay in a dangerous situation because you have no alternative.
We’ve made our life-support systems work like slot machines and then we act surprised when a bunch of people lose.
What I’m proposing — and developing in much more detail in the upcoming book — is a structural separation. Two economies, running in parallel.
The Market keeps doing Market-y things. Competition, innovation, disruption, fun socks… rock and roll everywhere our future isn’t on the line.
The Commons is the second economy, the one we need to build. It covers everything required for a good life in the modern world: healthcare, housing, childcare, energy, education, public transit, and so on.
The organizing principle of The Commons is simple: if a thing is required for life, it should not be for profit.
Now, let me clarify: this is not some kind of government takeover. The supply chains, the manufacturers, the innovators, the producers — all of that can still be competitive and market-driven. The Commons just governs access. Public access doesn’t require public production. This distinction matters enormously, and I’ll be going deep on it in the book.
And here’s the thing: this kind of arrangement isn’t theoretical, we just need to pull together pieces from different parts of the world.
In Vienna, Austria, about 60% of residents live in publicly owned or subsidized housing, all classes, not stigmatized, not segregated.
In Finland, education is free from primary school through doctoral degree. Not cheaper, not “accessible with loans”… free.
In Denmark, nearly 90% of children aged one to five attend daycare, every child is guaranteed a place, and a single parent spends 2% of their income on childcare. In the U.S., a single parent spends an average of 37%.
These structures don’t happen by accident, and they don’t naturally emerge from The Market. They come from civic leaders deliberately investing in the future.
Here’s what makes The Commons more than just a “nice idea” — it delivers a system-level solution for a system-level problem.
Right now, most people work because they have to. Not because they’re passionate, not because the work is meaningful, but because the alternative is an impossibility. Not having a full time job means no healthcare. It means losing your housing. It means losing your emotional support scaffolding (which I didn’t even really talk about!). It means the floor underneath you, holding up your whole life, disappears.
The Commons is a floor for everyone to stand on.
Here’s the really cool part: when the floor is guaranteed to be there — when survival is decoupled from employment — the entire dynamic between workers and employers evolves.
When this happens, The Market will have to compete for human workers on human terms. It will have to offer work worth doing, culture worth belonging to, leadership worth following.
This is the problem I’ve been trying to solve, and mostly failing to move the macro needle on, for the last twenty years of my life. I couldn’t do it because this isn’t a “point solution” type of problem.
The Commons is a system fix for a system problem.
And here’s the part that should matter to everyone listening, especially my FTE friends. Remember that wrong question we started with? “Am I going to need to become an entrepreneur?”
The reason that question feels so terrifying isn’t the entrepreneurship itself. You are creative and resourceful. You’re human, this what we ARE.
That question is mostly scary because of the absence of a floor.
A solid floor enables new business creation. Without something to stand on, “go become an entrepreneur” isn’t really freedom at all. It’s scary.
This two-economy path isn’t anti-capitalism. It’s actually going to raise the bar on capital, on competition, and help capitalism work the way it was supposed to.
The Commons is the infrastructure we need to land the coming transition away from Full Time Employment without our society crashing and burning. And A.I. is making the timeline a lot more urgent than most people realize.
In addition to fleshing this out in my upcoming book, I’m also in the very beginning stages of setting up a project to help create The Commons. If you have ideas or things we should think about or want to participate in some way please let me know in the comments or shoot an email to future@hellotomorrowpodcast.com.
The Commons is the thing we need to establish a new social contract in the U.S. that will genuinely work for everyone.
Leadership Lens
For my leader friends, here’s this week’s Leadership Lens.
The workforce you’re managing is increasingly anxious — not just about A.I. taking their jobs, but about what happens to their lives if it does. That anxiety is the Dysregulation Tax we’ve talked about before, and it is expensive. It shows up as reduced innovation, reduced creativity, reduced engagement.
You know this: people in survival mode do not do their best work.
So here’s my challenge to you: are you part of the solution or part of the problem?
Deloitte’s approach: “The job market is slack, so we can” is a bleak, heartless, shortsighted strategy that only works until it doesn’t. Until your best people leave for organizations that treat them better. Until the regulatory environment shifts. Until the political pressure builds. Don’t fall into that trap.
The leaders who win the next decade will be the ones who understand the transition to an A.I.-augmented workforce requires more investment in people, not less.
Here’s what else you can do: be an advocate for portable benefits. Support policy that decouples healthcare from employment. And do whatever you can to structure your own organization to actually deserve the workforce of the future.
The floor underneath workers is eroding. Your choices can accelerate that, or you can be one of the people helping build something better.
We need your leadership now, more than ever.
The Optimistic Rebellion
For all my friends, here’s this week’s Optimistic Rebellion.
The kind of “forced-entrepreneurship” moment we’re entering could be liberating. Here’s a delightful imagined future if you want some inspiration. More autonomy, more flexibility, more people building things they actually care about… that future is worth wanting.
But we have to build the floor first.
Entrepreneurship with a floor is freedom. You can take risks, try things, leave bad situations, build something new without gambling your family’s health on it. But this will require the creation of a new social contract. To get there, we must stop accepting the Full Time Employment model as a Law Of Nature.
We must also start demanding — from our representatives, our industry, our own organization — a better infrastructure that makes real choice possible. I call this The Commons.
The era of stable employment may genuinely be ending. That doesn’t have to be a tragedy. It could be the moment we finally replace the accidental, rickety, WWII-era workaround with something we actually design on purpose.
Let’s create the floor. Then we can actually get excited for what we can build on top of it.
