
WEDNESDAY, SEPTEMBER 2, 2026 · ISSUE #03
THE OPEN
Good morning.
Wednesday… yeeap, I know…
Far enough from Monday to feel accomplished.
Not close enough to Friday to become reckless.
Today we’re talking about something slightly more concerning than your calendar:
The beginning of your career.
Apparently we’ve been renovating it without installing all the stairs.
Let’s get to work.
BTW…. If you’re still here, good choice. You might actually enjoy this and further issues. If not, no drama, the exit is conveniently labeled “unsubscribe.”
BIG STORY
The career ladder is missing a few rungs
For years, younger workers have been accused of giving up on traditional careers.
They don’t want to climb the ladder.
They want side hustles.
They want flexibility.
They want to become creators.
They want to sell something called a “digital product” from Bali.
There may be another explanation.
The ladder itself has changed.
MIT professor emeritus Paul Osterman has spent decades studying the American labor market.
In new research based on a survey of more than 6,000 U.S. adults and nearly 100 interviews, he estimates that roughly 35% of the American workforce — more than 55 million people — now falls into what he calls “disposable” work.
That includes contractors, freelancers, gig workers and a large group of regular W-2 employees who are hired without much expectation that they’ll stay, advance or become deeply attached to the company.
And here’s the interesting part:
Gig work is only a small piece of the story.
Osterman estimates it at around 2% of the workforce.
The bigger shift is happening inside regular organizations.
Companies have become very good at hiring people for work.
They have become less consistent at creating places for those people to go next.
That matters because the old career bargain involved more than a paycheck.
You joined.
You learned.
Someone more experienced gave you work you were slightly unqualified to do.
Eventually, you became the experienced person.
Now employers increasingly want the experienced person immediately.
That creates a wonderfully efficient system:
ENTRY-LEVEL POSITION
Requirements:
3–5 years experience.
Executive communication skills.
Strategic thinking.
Industry expertise.
Leadership ability.
Salary:
Entry-level.
There are legitimate business reasons behind some of this.
Teams are leaner.
Managers have less time.
Companies want employees who can contribute quickly.
Training costs money.
But careers require apprenticeships somewhere.
You cannot hire experienced people forever without occasionally creating one.
That may be the real problem facing younger workers.
They haven’t stopped wanting careers.
They may simply be arriving at the ladder while someone is removing the bottom steps.

WORTH KNOWING
01 / There are 7.27 million job openings. Hiring still looks tired.
The latest U.S. labor data shows 7.27 million job openings in July.
That sounds encouraging.
Hiring actually fell to about 5.05 million, while layoffs remained relatively low.
In other words:
The jobs exist.
Companies are just being cautious about filling them.
The labor market continues to resemble a party where nobody wants to leave and nobody new is getting through the door.
02 / Private hiring slowed again in August
ADP reported that private employers added just 38,000 jobs in August, below economists’ expectations.
July was revised slightly higher, but the overall message remains the same:
Hiring is moving.
Slowly.
The bigger government jobs report arrives Friday.
Everyone please prepare to interpret the same labor market twelve different ways.
03 / Bosses say Gen Z isn’t “workplace ready”
Employers continue complaining that younger workers lack communication, professionalism and critical-thinking skills.
Colleges are getting blamed.
Young workers are getting blamed.
Employers, interestingly, are spending less time talking about how much training companies used to provide themselves.
A surprisingly efficient arrangement.
Everyone agrees someone should train new workers.
Preferably someone else.
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WORK SMARTER
Start a brag file
Create a document.
Call it whatever you want.
Mine would probably be:
Things I Did So I Remember Them During Performance Review Season
Every Friday, add three things:
Something you finished.
Something you improved.
Something somebody thanked you for.
That’s it.
Projects disappear into Slack.
Numbers disappear into dashboards.
Compliments disappear into email threads.
Six months later your manager asks:
“What were your biggest contributions this year?”
And your brain responds:
I attended several meetings.
A brag file gives you evidence.
Use it for reviews, raises, résumés, interviews or the awkward moment when somebody asks what exactly you do around here.
Five minutes a week.
Your future self can buy you coffee.
MONEY
Your salary isn’t the only thing you’re negotiating
When people compare jobs, salary gets almost all the attention.
It shouldn’t.
Take two jobs paying $100,000.
One includes:
four weeks vacation
a strong 401(k) match
remote flexibility
good health insurance
a reasonable commute
The other includes:
two weeks vacation
no meaningful match
five days in the office
expensive insurance
a 50-minute commute
Those are not two $100,000 jobs.
Before accepting an offer, make a simple spreadsheet.
Column one:
What they pay me.
Column two:
What working there costs me.
Commute.
Parking.
Insurance.
Lost retirement match.
Extra childcare.
Vacation.
Time.
Then compare.
Compensation is the package.
Salary is simply the number companies know you’ll screenshot first.
STILL MONDAY
ENTRY-LEVEL POSITION
Experience required: 5 years
Management experience: Preferred
Industry expertise: Required
Leadership skills: Essential
Salary: Entry-level
Training provided: Minimal
Career growth: We’ll discuss that in your annual review.
Application question:
“Why do you think you’re ready for an entry-level role?”
ONE MORE THING
Your first career may not be your longest one
There’s a tendency to treat the first job after school as if you’re selecting a character in a video game.
Choose carefully.
This will define your existence.
It won’t.
Your first job needs to do something much simpler:
Teach you something valuable enough to make the second job easier to get.
That’s a considerably less terrifying decision.
Technically Wednesday. Emotionally Monday.
See you tomorrow.
— The Still Monday Desk

