The Broken Deal: Why “Work Hard, Get a Degree” Stopped Working
by Antony Barran
When I was coming up, the deal was simple.
Work hard. Get some education. Show up on time. Don’t be a jerk.
If you did that, you might not get rich, but you’d land on your feet. There were rungs on the ladder. There was a path, even if it wasn’t glamorous.
That deal is gone.
Today I talk to people in their twenties – smart, driven, doing everything they were told to do – and they’re exhausted before they even get started. Degree in hand, debt on their back, living with their parents, grinding in jobs that don’t use what they studied, being told they’re “entitled” for wanting… a stable life.
I don’t buy that story.
The problem isn’t that this generation is softer. The problem is that the rules changed and nobody bothered to update the instruction manual.
This first piece is about naming what broke. Prosperity-Works is about fixing it. But if we don’t start with an honest diagnosis, everything else is just marketing copy.
The Old Deal: A Pipeline with Real Rungs
If you came of age in the 80s or 90s, this will feel familiar.
The formula looked like this:
Finish high school.
Maybe college, maybe not – but if you did get a degree, it actually meant something.
Land an entry-level job where the title had the magic words: “Will train” or “No experience necessary.”
Learn on the job.
If you showed up and didn’t set anything on fire, you moved up.
The job wasn’t just a paycheck. It was a bundle:
A modest salary
Health insurance the company mostly paid for
A pension or a strong retirement plan
Some paid time off
And an unspoken assumption: if you didn’t screw up badly, you’d still be there next year
In other words, it was a pipeline. You entered at the bottom and were expected to move forward. Nobody thought it was all sunshine and roses. But the steps existed, and they were visible.
You could be 23, renting a dingy apartment, driving a beat-up car, and still have a reasonable belief that in five years you’d be in a better place.
That belief matters.
The New Reality: A Filter with Fewer Seats
Now let’s talk about today.
We pushed “college for all” for thirty years. We doubled the number of degrees. We told every kid that the safe path ran straight through a four-year campus. We wrapped it all in glossy marketing: dorm life, football games, “follow your passion.”
What we didn’t do was double the number of good jobs on the other side.
So here’s where we are:
A bachelor’s degree is no longer a differentiator. It’s an entry ticket just to be considered.
Many “entry-level” job postings now demand 2–3 years of experience.
The grunt work that used to be training ground – basic analysis, data entry, admin support – has been automated or outsourced.
The system doesn’t function like a pipeline anymore. It functions like a filter.
The message to a 24-year-old today is basically:
“Congratulations. You paid a fortune for the right to stand in this line. There are fewer seats than players, and if you don’t get one quickly, the interest meter on your debt keeps running.”
It’s not just that it’s hard. It’s structurally different.
The Barista with a Bachelor’s, the Counselor with a Master’s
People joke about the “barista with a bachelor’s.” It’s not funny anymore.
Underemployment – working in jobs that don’t require your degree – used to be a brief phase. You took the retail job, the restaurant job, the temp assignment, and then the economy absorbed you. You moved into something closer to your field.
Now, a lot of young adults get stuck there for years. That early stall doesn’t just bruise the ego; it permanently dents lifetime earnings. You don’t build the skills, the network, or the confidence you need when it counts most.
For women, especially, there’s another layer.
We told an entire generation of young women that a Master’s degree was the fast track: more options, more pay, more security. In reality, for a huge swath of fields – education, social work, counseling, nonprofits – the math is upside down:
Tuition has exploded.
Wages in those fields have barely moved.
And many of those low-ROI programs are dominated by women.
So you end up with a 27-year-old with a Master’s, doing work that matters – teaching, counseling, community work – and she’s staring at a debt load that would scare a cardiologist.
She didn’t get scammed on work ethic. She got scammed on pricing.
Retirement: The Promise We Broke Twice
There’s another piece of the old deal that quietly disappeared: how you retire.
For our parents’ generation, the picture looked like this:
Work 25–30 years for a company.
The company runs a pension.
You retire with a guaranteed monthly check for life.
Was it perfect? No. But it was simple. The risk sat on the company’s balance sheet, not on the 24-year-old trying to pick mutual funds on their phone.
Then we were told: pensions are old-fashioned, rigid, too expensive. Don’t worry – we have something better.
Enter the 401(k) era, sold with three big promises:
You’re in control. You get to choose your investments.
The market always goes up over time. Just stay the course.
We’ll match your contributions. Free money.
For a while, pieces of that worked. Employer matches were real. There was at least an attempt to say, “We’re shifting the structure, but we’re still in this with you.”
And then, slowly, the second break of the promise:
Matches got smaller, or disappeared.
Vesting schedules got longer.
More people ended up in jobs with no retirement plan at all – especially as gig work, temping, and contracting exploded.
So here’s the view from a 25-year-old today:
No pension. That disappeared before they were born.
Maybe a 401(k), but only if they land one of the shrinking number of jobs that offer it.
No match at all if they’re freelance, on a contract, or bouncing between short-term roles.
Full responsibility for figuring out investing, taxes, and risk… with no training and inconsistent income.
We didn’t just move from pensions to 401(k)s.
We moved from “we’ll carry the risk with you” → to “you’re on your own, but we’ll help a bit” → to “good luck, hope you watched enough YouTube videos about index funds.”
That is a massive, generational shift in risk that almost nobody talks about out loud.
And it matters, because when young people say they don’t see a path to retirement, they’re not being dramatic. We took away the guaranteed path, handed them a do-it-yourself kit with missing pieces, and then started pulling away the tools.
The Ticket Got More Expensive. The Ride Got Shorter.
Let’s go back to student debt for a second, because it sits on top of all of this.
If you strip out all the politics and just look at it like a businessperson, the story looks like this:
The cost of the ticket (tuition) shot through the roof.
The value of the prize (extra earnings, stability, real retirement) flattened out.
The risk – if you graduate into a rough job market or get underemployed – sits squarely on the backs of 20-somethings.
In the 90s, you could take on a modest amount of debt, land a decent job with benefits and a retirement plan, and pay it off in a few years. It wasn’t fun, but it was manageable, and you could still imagine retiring at a reasonable age.
Today, it’s not unusual to see:
Bachelor’s graduates with $30k–$40k in debt.
Master’s graduates with $60k–$80k+ in debt.
Jobs with no pension, shaky 401(k) support, and no guarantee you’ll still be there in two years.
If you hit a recession, a layoff, or a health issue early in your career, the debt doesn’t care. The rent doesn’t care. The missing pension doesn’t suddenly reappear because the economy hiccuped.
We used to talk about education and employment as a path to wealth. For a lot of young people, particularly in the wrong programs and the wrong jobs, it now feels more like a path to permanent financial anxiety.
The Delay of Adulthood Isn’t a Character Flaw
Now layer housing, healthcare, and this retirement uncertainty on top of all that.
A lot of folks my age look at younger adults living at home and say, “In my day, we just moved out and figured it out.”
Well, in our day:
Rent consumed a smaller share of income.
Starter homes were priced at three-ish times a household salary, not five to seven.
Entry-level jobs came with benefits, a retirement plan, and a decent chance you’d still be there in a year.
If you’re 25 today, here’s what your reality might look like:
You’re working – maybe more than one job – but neither offers benefits.
You’re paying for your own health insurance or rolling the dice without it.
Your student loan payment eats a chunk of your disposable income, or it’s looming in deferment.
You have no pension, a spotty or nonexistent 401(k), and no idea what retirement is supposed to look like.
Rents are high enough that moving out on your own means you never save.
So you move back home. Or you never leave. Not because you’re lazy, but because you’re doing basic math.
On paper, it looks like “failure to launch.” In reality, it’s a rational response to being handed all the risk with far fewer tools.
Why the Avocado Toast Lecture Needs to Die
Here’s the part that really grates on me.
We have an entire generation that:
Did what we told them.
Took on the debt we encouraged.
Accepted the end of pensions because we promised 401(k)s would be “even better.”
Entered an economy we designed.
And when it doesn’t work, the loudest voices say, “Well, if they just stopped buying fancy coffee…”
That’s nonsense.
You cannot “stop buying lattes” your way out of:
A structurally narrower entry-level job market
A benefits package that’s been silently stripped down
The disappearance of guaranteed retirement and the erosion of 401(k) support
A housing market distorted by decades of policy, speculation, and scarcity
A debt load that would have looked insane to a guidance counselor in 1995
Personal responsibility matters. I’ve built my life on that belief. But there’s a difference between asking people to show up and earn it, and handing them a rigged game and then blaming them when they lose.
Right now, they’re being told to play a game that doesn’t exist anymore.
So What Do We Do About It?
This is where Prosperity-Works comes in.
I’m not interested in writing one more think-piece about how hard it is for young people. They know it’s hard. Their parents are starting to feel it too as their adult kids boomerang home, delay families, and can’t get a foothold.
What I am interested in is rebuilding the bottom rungs of the ladder – locally, practically, and in a way that actually works for:
Workers under 30 who need stability, training, benefits, and a real shot at building wealth over time.
Small and mid-sized businesses that can’t afford to offer “Google-level” packages on their own but still want to do right by their people.
Communities like ours in Southwest Washington that are tired of being told to wait for a solution from somewhere else.
At its core, Prosperity-Works is about this simple idea:
What if we stopped lecturing people about the old deal and started building a new one that actually matches the economy we live in?
In the next piece, I’m going to dig into how jobs have quietly been unbundled – how we took apart the package of wages, benefits, retirement, and stability – and how a different model can rebundle those pieces in a way that works for workers and employers.
Because if we want our kids and grandkids to have a shot at the same basic life trajectory we took for granted, we’re going to have to stop waiting for permission and start building the infrastructure of a new deal ourselves.
