The Great Unbundling: How We Quietly Cut Young Workers’ Pay by 30%
In the first piece, I talked about the death of the old deal: work hard, get some education, start at the bottom, move up. The ladder might have been rickety, but it existed.
This one is about something quieter and, in some ways, more brutal:
We didn’t just make it harder to get a job.
We changed what a job is—and pretended nothing happened.
On paper, wages have “risen.” In reality, we’ve spent 30 years quietly stripping pieces out of the compensation package and shifting risk from companies to 24-year-olds who can barely afford new tires.
That’s what I mean by the Great Unbundling.
Back When a Job Was a Bundle, Not Just a Wage
If you came up through the workforce anytime before, say, the mid-2000s, this will sound familiar.
A “real job” meant:
You were a W-2 employee, not a 1099 contractor.
Your employer covered most of your health insurance.
There was a retirement plan—maybe a pension, maybe a solid 401(k) match.
You got paid time off. If you got sick or took a vacation, the lights stayed on.
The company provided your tools—your computer, your phone, sometimes even your car.
Was every job like this? Of course not.
But that was the template for a basic, middle-class job. When you sat down to negotiate an offer, the conversation was never just “What’s my salary?” It was:
What’s the salary?
What’s the health plan?
What’s the match?
How much vacation?
Is there a bonus?
It was a bundle.
And that bundle is what made the math of adulthood work.
How We Unbundled the Job (While Calling It “Freedom”)
Fast forward to today.
A shocking number of people under 30 are working in arrangements that would barely have counted as “having a job” 30 years ago:
They’re “contractors” or “consultants” or “TVCs” (Temps, Vendors, Contractors).
They sit in the same office as full-timers, doing similar work.
But they:
Get no employer-paid health insurance.
Get no retirement contributions.
Get little or no paid time off.
Can be turned off like a light switch at the end of a quarter.
We dressed this up as flexibility and freedom:
“You’re your own boss.”
“You can work from anywhere.”
“You’re an entrepreneur.”
Look under the hood and it’s simple: we took pieces that used to be included in the job, and we shoved them back onto the individual’s plate.
Health care? Your problem.
Retirement? Your problem.
Taxes? Your problem.
Risk of a downturn? Your problem.
The company still gets the work.
The shareholder still gets the earnings.
The young worker gets… a laptop and a “great opportunity.”
“But Don’t Hourly Workers Get PTO Now?” (The Washington Reality)
In Washington State, there has been some pushback on this trend—and it’s important to acknowledge it.
Here, even hourly employees earn paid sick leave by law. In some places, local rules go further. That’s a good thing. It’s a floor that didn’t exist thirty years ago.
But:
It’s a minimum, not a full bundle.
Sick leave is not the same as real vacation time.
And those protections apply to employees—not to the growing number of people pushed into 1099 contractor status, temp agencies, or gig platforms.
So yes, a lot of hourly workers in Washington have a small cushion now when they get sick. That’s progress.
It doesn’t change the bigger truth: the modern job has been unbundled. The legal floor doesn’t replace what used to be baked-in—healthcare, retirement, and PTO as part of a coherent package. And if you’re one of the many young people classified just outside “employee” status, you don’t even get the floor.
The Hidden Pay Cut: Health Care, Taxes, and Time Off
Let’s strip the emotion out of it and look at the math.
Take two 25-year-olds:
1995 Anthony:
Makes $35,000 as a W-2 employee.
Employer pays most of his health insurance premium.
Employer contributes to a pension or 401(k).
Employer pays half of FICA (Social Security and Medicare).
He gets 2 weeks of paid vacation plus sick days.
2025 Ava:
Makes $50,000 doing similar work as a 1099 contractor or TVC.
Buys her own health insurance on the exchange.
No employer retirement contributions.
Pays the full 15.3% self-employment tax.
Little or no paid time off beyond whatever the law requires—and if she’s a true contractor, even those protections don’t apply. If she doesn’t work, she doesn’t get paid.
On paper, it looks like Ava is doing better.
In reality, by the time you:
Subtract what she pays for health insurance,
Add the extra FICA she’s paying,
Factor in the lack of retirement match or pension,
And account for unpaid time off (because nobody works 52 perfect weeks a year),
her real compensation is meaningfully lower than Anthony’s, adjusted for inflation.
We’ve managed to create a world where a $50k “opportunity” can easily be worth less than a $35k “boring job” was 30 years ago.
That’s the Great Unbundling in one snapshot.
Pensions → 401(k)s → “You’re On Your Own”
We did the same thing with retirement.
First, we removed pensions and said:
“Don’t worry, you’ll do even better with a 401(k). You’re in control now.”
Then, once everyone had adjusted to that, we:
Shrunk the matches.
Stretched the vesting schedules.
Classified more people as contractors, temps, or gig workers — which conveniently come with no retirement plan at all.
So instead of:
“Work 30 years and we’ll pay you a check for life,”
we now tell a 25-year-old:
“Open an account you don’t understand, invest in markets you don’t control, and contribute out of a paycheck that barely covers rent and student loans. Also, don’t make any mistakes for 40 years.”
And if they say, “I don’t see how I’ll ever retire,” we act like they’re being dramatic.
They’re not. They’re reading the fine print.
“You Have a Job” vs. “You Have a Stake”
Here’s the deeper problem: we’ve turned employment into rental.
In the old bundled model:
You had a stake in the company’s future.
If the company did well, your pension was safer, your bonus was bigger, your job was more stable.
The company’s success and your long-term security were at least loosely tied together.
In the unbundled model:
You are a line item that can be erased.
You don’t share in the upside, but you absolutely share in the downside.
When the quarter gets tight, you’re gone. When things improve, they don’t call you back; they post a new contract.
You’re not building a career. You’re renting your time.
And there’s no equity—financial or emotional—in renting your time.
Why This Hits Under-30s the Hardest
If you’re 50 and reading this, there’s a good chance you rode at least part of your career inside the old bundle. You had years of:
Employer-subsidized healthcare
Consistent retirement contributions
Real PTO
Some level of job stability
Even if it wasn’t glamorous, those years were compounding in the background.
If you’re 25 today and you spend your entire twenties in unbundled “jobs”:
You don’t build wealth.
You don’t build a stable credit profile.
You don’t contribute meaningfully to retirement.
You don’t get consistent healthcare—so one bad medical event can blow the whole thing up.
Then, when you hit 30 and try to “get serious,” you find out you’re a decade behind and all the asset prices (homes, etc.) moved without you.
We like to talk about this as if it’s an attitude problem. It’s not. It’s a compounding problem. You can’t compound what you never get the chance to start.
So Where Does Prosperity-Works Fit In?
Prosperity-Works is my attempt to answer a simple question:
“If the modern economy is going to stay flexible, how do we rebuild the bundle without killing small businesses?”
We are not going back to giant single-employer life-time careers. That ship has sailed, for better or worse.
But we can build a new structure that:
Gives workers a W-2 home base instead of being permanently 1099.
Pools employers so they can share the cost of good benefits instead of each trying (and failing) to do it alone.
Re-bundles:
Health insurance
Retirement contributions
Paid time off
Training and upskilling
under one regional umbrella.
Think of Prosperity-Works as a shared backbone:
We are the employer of record.
Workers stay on our books, with continuous benefits and history.
They work at local businesses across Southwest Washington—farms, restaurants, shops, marinas, logistics, manufacturers—who pay for their time without carrying the full HR burden alone.
For workers, that means:
One W-2 identity.
Real benefits.
The ability to move between employers as seasons and opportunities change without resetting everything to zero.
For employers, especially small ones, it means:
They can offer a real bundle—health, retirement, PTO—without building a massive HR department.
They can flex staffing up or down without destroying someone’s entire life.
They can compete for talent on the things that matter, not just on “we’re like a family” posters.
Rebundling the Job Without Rebuilding the Old Machine
I’m not nostalgic for the old world in every way.
Some companies abused the old system.
Some pensions were badly managed.
Some careers trapped people in places they were miserable.
I’m not trying to resurrect 1975.
What I am saying is this:
We’ve pushed all the risk down the ladder. We’ve unbundled the job and then acted shocked that young workers don’t feel secure, can’t buy homes, and don’t believe in retirement.
If we want different outcomes, we need different infrastructure.
Prosperity-Works is my version of that infrastructure: rebundle the job—benefits, stability, retirement—while keeping the flexibility that modern life demands and giving small businesses a path that doesn’t crush them with compliance and cost.
In the next piece, I’m going to get very specific about how this plays out here, at home—
in Pacific, Wahkiakum, Cowlitz, Lewis, Skamania, and Clark Counties.
Because it’s one thing to talk about this in theory.
It’s another to ask: “What would it feel like to be 24 in Longview or Ilwaco if this existed?”
Gemini edited version
The Great Unbundling: How We Quietly Cut Young Workers’ Pay by 30%
In the first piece, I talked about the death of the old deal: work hard, get some education, start at the bottom, move up. The ladder might have been rickety, but it existed. This one is about something quieter and, in some ways, more brutal: We didn’t just make it harder to get a job. We changed what a job is—and pretended nothing happened.
On paper, wages have “risen.” In reality, we’ve spent 30 years quietly stripping pieces out of the compensation package and shifting risk from companies to 24-year-olds who can barely afford new tires. That’s what I mean by the Great Unbundling.
Back When a Job Was a Bundle, Not Just a Wage
If you came up through the workforce anytime before, say, the mid-2000s, this will sound familiar. A “real job” meant:
You were a W-2 employee, not a 1099 contractor.
Your employer covered most of your health insurance (often paying 90–100% of the premium with a $200 deductible).
There was a retirement plan—maybe a pension, maybe a solid 401(k) match.
You got paid time off. If you got sick or took a vacation, the lights stayed on.
The company provided your tools—your computer, your phone, sometimes even your car.
Was every job like this? Of course not. But that was the template for a basic, middle-class job. When you sat down to negotiate an offer, the conversation was never just “What’s my salary?” It was:
What’s the salary?
What’s the health plan?
What’s the match?
How much vacation?
Is there a bonus?
It was a bundle. Economists estimate that in the 90s, these non-cash benefits added roughly 30% to 40% to the value of your salary. And that bundle is what made the math of adulthood work.
How We Unbundled the Job (While Calling It “Freedom”)
Fast forward to today. A shocking number of people under 30 are working in arrangements that would barely have counted as “having a job” 30 years ago:
They’re “contractors” or “consultants” or “TVCs” (Temps, Vendors, Contractors).
They sit in the same office as full-timers, doing similar work.
But they:
Get no employer-paid health insurance.
Get no retirement contributions.
Get little or no paid time off.
Can be turned off like a light switch at the end of a quarter.
We dressed this up as flexibility and freedom: “You’re your own boss.” “You can work from anywhere.” “You’re an entrepreneur.”
Look under the hood and it’s simple: we took pieces that used to be included in the job, and we shoved them back onto the individual’s plate.
Health care? Your problem.
Retirement? Your problem.
Taxes? Your problem. (And that problem costs you an extra 7.65% off the top).
Risk of a downturn? Your problem.
The company still gets the work. The shareholder still gets the earnings. The young worker gets… a laptop and a “great opportunity.” Surveys show nearly 70% of recent graduates are doing some form of gig work—not because they love "hustle culture," but because the traditional jobs aren't there.
“But Don’t Hourly Workers Get PTO Now?” (The Washington Reality)
In Washington State, there has been some pushback on this trend—and it’s important to acknowledge it. Here, even hourly employees earn paid sick leave by law. In some places, local rules go further. That’s a good thing. It’s a floor that didn’t exist thirty years ago.
But:
It’s a minimum, not a full bundle.
Sick leave is not the same as real vacation time.
And those protections apply to employees—not to the growing number of people pushed into 1099 contractor status, temp agencies, or gig platforms.
So yes, a lot of hourly workers in Washington have a small cushion now when they get sick. That’s progress. It doesn’t change the bigger truth: the modern job has been unbundled. The legal floor doesn’t replace what used to be baked-in—healthcare, retirement, and PTO as part of a coherent package. And if you’re one of the many young people classified just outside “employee” status, you don’t even get the floor.
The Hidden Pay Cut: Health Care, Taxes, and Time Off
Let’s strip the emotion out of it and look at the math. Take two 25-year-olds:
1995 Anthony:
Makes $35,000 as a W-2 employee.
Employer pays most of his health insurance premium (Copays are ~$10).
Employer contributes to a pension or 401(k).
Employer pays half of FICA (Social Security and Medicare).
He gets 2 weeks of paid vacation plus sick days.
2025 Ava:
Makes $50,000 doing similar work as a 1099 contractor or TVC.
Buys her own health insurance on the exchange (Average deductible is now over $1,700).
No employer retirement contributions.
Pays the full 15.3% self-employment tax.
Little or no paid time off beyond whatever the law requires—and if she’s a true contractor, even those protections don’t apply. If she doesn’t work, she doesn’t get paid.
On paper, it looks like Ava is doing better. In reality, by the time you:
Subtract what she pays for health insurance (often $300–$500/month),
Add the extra FICA she’s paying (an immediate $3,800+ tax hit Anthony didn't have),
Factor in the lack of retirement match or pension,
And account for unpaid time off (because nobody works 52 perfect weeks a year), her real compensation is meaningfully lower than Anthony’s, adjusted for inflation. We’ve managed to create a world where a $50k “opportunity” can easily be worth less than a $35k “boring job” was 30 years ago. That’s the Great Unbundling in one snapshot.
Pensions → 401(k)s → “You’re On Your Own”
We did the same thing with retirement. First, we removed pensions and said: “Don’t worry, you’ll do even better with a 401(k). You’re in control now.” Then, once everyone had adjusted to that, we:
Shrunk the matches.
Stretched the vesting schedules.
Classified more people as contractors, temps, or gig workers — which conveniently come with no retirement plan at all.
So instead of: “Work 30 years and we’ll pay you a check for life,” we now tell a 25-year-old: “Open an account you don’t understand, invest in markets you don’t control, and contribute out of a paycheck that barely covers rent and student loans. Also, don’t make any mistakes for 40 years.” And if they say, “I don’t see how I’ll ever retire,” we act like they’re being dramatic. They’re not. They’re reading the fine print.
“You Have a Job” vs. “You Have a Stake”
Here’s the deeper problem: we’ve turned employment into rental. In the old bundled model:
You had a stake in the company’s future.
If the company did well, your pension was safer, your bonus was bigger, your job was more stable.
The company’s success and your long-term security were at least loosely tied together.
In the unbundled model:
You are a line item that can be erased.
You don’t share in the upside, but you absolutely share in the downside.
When the quarter gets tight, you’re gone. When things improve, they don’t call you back; they post a new contract.
You’re not building a career. You’re renting your time. And there’s no equity—financial or emotional—in renting your time.
Why This Hits Under-30s the Hardest
If you’re 50 and reading this, there’s a good chance you rode at least part of your career inside the old bundle. You had years of:
Employer-subsidized healthcare
Consistent retirement contributions
Real PTO
Some level of job stability
Even if it wasn’t glamorous, those years were compounding in the background. If you’re 25 today and you spend your entire twenties in unbundled “jobs”:
You don’t build wealth.
You don’t build a stable credit profile (which helps explain why the age of first-time homebuyers has jumped from 29 to ~35).
You don’t contribute meaningfully to retirement.
You don’t get consistent healthcare—so one bad medical event can blow the whole thing up.
Then, when you hit 30 and try to “get serious,” you find out you’re a decade behind and all the asset prices (homes, etc.) moved without you. We like to talk about this as if it’s an attitude problem. It’s not. It’s a compounding problem. You can’t compound what you never get the chance to start.
So Where Does Prosperity-Works Fit In?
Prosperity-Works is my attempt to answer a simple question: “If the modern economy is going to stay flexible, how do we rebuild the bundle without killing small businesses?”
We are not going back to giant single-employer life-time careers. That ship has sailed, for better or worse. But we can build a new structure that:
Gives workers a W-2 home base instead of being permanently 1099.
Pools employers so they can share the cost of good benefits instead of each trying (and failing) to do it alone.
Re-bundles:
Health insurance
Retirement contributions
Paid time off
Training and upskilling under one regional umbrella.
Think of Prosperity-Works as a shared backbone:
We are the employer of record.
Workers stay on our books, with continuous benefits and history.
They work at local businesses across Southwest Washington—farms, restaurants, shops, marinas, logistics, manufacturers—who pay for their time without carrying the full HR burden alone.
For workers, that means:
One W-2 identity.
Real benefits.
The ability to move between employers as seasons and opportunities change without resetting everything to zero.
For employers, especially small ones, it means:
They can offer a real bundle—health, retirement, PTO—without building a massive HR department.
They can flex staffing up or down without destroying someone’s entire life.
They can compete for talent on the things that matter, not just on “we’re like a family” posters.
Rebundling the Job Without Rebuilding the Old Machine
I’m not nostalgic for the old world in every way.
Some companies abused the old system.
Some pensions were badly managed.
Some careers trapped people in places they were miserable.
I’m not trying to resurrect 1975. What I am saying is this: We’ve pushed all the risk down the ladder. We’ve unbundled the job and then acted shocked that young workers don’t feel secure, can’t buy homes, and don’t believe in retirement. If we want different outcomes, we need different infrastructure. Prosperity-Works is my version of that infrastructure: rebundle the job—benefits, stability, retirement—while keeping the flexibility that modern life demands and giving small businesses a path that doesn’t crush them with compliance and cost.
In the next piece, I’m going to get very specific about how this plays out here, at home—in Pacific, Wahkiakum, Cowlitz, Lewis, Skamania, and Clark Counties. Because it’s one thing to talk about this in theory. It’s another to ask: “What would it feel like to be 24 in Longview or Ilwaco if this existed?”
