The hiring crisis nobody saw coming

Hey everyone,

It used to be that “entry-level” positions were almost never the person’s actual first job. Because kids bagged groceries or cut lawns or worked retail. 

Not these days. 

Twenty-somethings show up with their parents. Basic workplace norms like showing up on time, dealing with a difficult customer, handling small adversity – these are foreign concepts.

And over the last few decades, we've lost over half of America's working teenagers. Most business owners have no idea why or what it means for their hiring pipeline.

Let’s unpack why this happened and what it means for our businesses.

Small changes compound into catastrophe

What killed teenage summer jobs wasn't one thing.

First, grandparents. The 65+ workforce has jumped from 11% to 19%. Employers quickly figured out that the 60-year-old retiree shows up on time, doesn't check their phone, and actually wants to be there. Easy choice.

Then immigrant labor, which hit teenagers three times harder than adult workers. Food prep, cashiers, valet parking — these low-level jobs are now filled year-round by people with no school schedules.

Add automation. Self-checkout replaced teenage cashiers. I’ve read about some restaurants that use overseas workers via Zoom to run registers. Wild.

Finally, regulations made teenagers expensive and annoying to hire. Higher insurance costs because teens get injured more. Hour restrictions. When my own teenage kids tried getting jobs here in San Antonio, employers took one look and said, "You can only work after school, that won't work for me."

None of these changes felt dramatic individually.

But 45 years of small shifts, all pushing in the same direction, and your entry-level pipeline just evaporated.

The training ground disappeared

Teenage jobs weren’t just about cheap labor for employers. They were where people learned to work.

How to show up on time. Handle an angry customer. Deal with small workplace adversity when the stakes are low.

My first summer job was lifeguarding at a pool in San Antonio. I learned some hard lessons about showing up and delivering on my commitments.

Without that, we’re seeing the consequences:

Twenty-somethings with zero work experience before their first career job, who don’t know not to bring mom to their interviews.

There’s an economic trend, too: kids from families earning under $150k are half as likely to get a summer job compared to wealthier kids. 

And while parents are pushing kids into college prep and enrichment programs, admissions counselors are saying they'd rather see a meaningful summer job than some expensive certificate.

Structural problems need structural solutions

It’s a doom loop: fewer teenagers have job experience → employers hire them less → even fewer get experience → employers avoid them more.

Summer 2026 is projected to be the worst teenage job market in history.

So if your business hires young talent, what can you do? 

It’s not about writing better job ads, because your labor pool has fundamentally changed. 

And finally: don’t expect them to act like the candidates you’re used to. I’m not saying lower your standards, but be open-minded about their differences. 

(A few years ago I wrote this list of 10 do’s and don’ts for working with Gen Z.)

The companies that adapt to the new reality will win. The ones waiting for things to "go back to normal" won't.

A quick Proud Dad moment: 

Our family business is selling fireworks in Texas, and my son Seth ran one of our stands leading up to New Years 2024. 

Basically a crash course in running his own business for 12 days. He was responsible for inventory, managing people, keeping the site secure, wrangling signage, dealing with competitors… the works. He even slept in the trailer with a fire extinguisher to make sure the whole thing didn’t go up in flames. 

I was super proud of him. And he even turned a profit. (He made daily updates you can watch here.)

It’s an opportunity I wish more kids could have. But I don’t know how many would take it.

Thanks for reading!

Michael

P.S. Reminder - come out next Wednesday, and bring your questions about business buying tradeoffs! RSVP for free right here. Everyone who signs up will get the recording.

P.P.S. I posted a teaser to this topic on Twitter. It got a ton of great responses, and some fun nuance and personal stories. Join the conversation here!