🚪 Breaking In: The Door Isn't Opening. So Build Your Own.

WorkLifeFuture | Guidance for parents supporting emerging adults in the age of AI & automation

Happy Tuesday.

Let me start with something that might sound counterintuitive given everything you're watching your kid go through right now.

Scott Galloway — NYU professor, author, someone who's built a career reading where things are going — has been saying this out loud lately:

"The biggest risk for young people today is waiting too long to take action."

And Mark Cuban:

"There has never been a better time to start a business than right now — because technology has leveled the playing field."

These aren't motivational posters. These are serious people pointing at something real.

And here's what I'd add from 35 years of watching careers unfold:

The young people who feel stuck right now — the ones applying into the void, refreshing their inboxes, doing everything right and hearing nothing — may be sitting closer to this opportunity than they realize.

For a meaningful slice of new graduates, the early-career, white collar pipeline feels unusually narrow right now. Applications disappear. Interview processes stall. Even strong candidates are waiting longer than anyone expected. It's heartbreaking.

I'm talking about really bright, talented young people. I should know — I hired a bunch of 'em.

And don't listen to folks who say it's all their fault.

It isn't a motivation problem. It's structural.

Technology is reshaping how organizations think about entry-level work. Employers are cautious. Competition has intensified. For graduates without strong signaling advantages — top-tier school, deep network, prior connections — the margin for error has narrowed considerably.

I expect this tightness to persist before it improves.

The old playbook isn't enough anymore.

So what is?

At the exact moment traditional hiring has tightened, the friction involved in starting something real has dropped dramatically.

Cuban is right. The playing field has shifted.

I like “Gary Vee” (Vaynerchuk) because he is even more blunt:

"If you’re young right now, the cost of starting a business is basically zero."

A motivated 22-year-old today can build a professional website, write marketing copy, create a brand, draft basic contracts, handle customer communications, and analyze a local market — all with AI tools that cost very little. What used to require a team, startup capital, and months of runway now takes one person, a laptop, and a willingness to figure it out.

Early data is beginning to reflect what many are sensing. Nearly half of new businesses formed last year — 47% — reported using generative AI, up from just 21% the year prior. And 81% of those founders said AI helped them move faster and operate more efficiently.

This isn't just a tech-sector story. These are small businesses, solo operators, and young people choosing to build rather than wait.

Another notable shift: Women now represent roughly half of new business owners, up significantly from just a few years ago. Representation among Black and Hispanic founders has also increased meaningfully. The tools are widening access.

I think about a young woman I heard about recently — communications degree, six months of applications, nothing landing. She started offering one simple service to local small businesses: using AI to improve their customer follow-up. Emails that actually get sent. Review requests that don't get forgotten. She now has four paying clients. She's learning faster than she would have in any entry-level role she applied for.

That path would have been much harder to start even three years ago.

My 20-year-old son, Whit, is still a few years away from graduating. But like many young people right now, he's been digging into AI tools out of pure curiosity — exploring how agents work, building small experiments, testing what's possible. He feels empowered. I love the thrill in his voice when he shares something he's built (and gives me tips!)

What strikes me watching him isn't the specific thing he's building.

It's the posture.

He's not waiting to be given access. He's figuring out what he can make. Just like I did way back when getting my hands on my first Macintosh computer.

I suspect that instinct — build first, ask permission later — is exactly what this moment rewards.

Galloway frames this in terms of leverage:

"Young people should think less about finding the perfect job and more about building leverage."

Over 35 years of hiring, I've seen this repeatedly. When someone walks into an interview and says, "I started something," I lean forward. Every time. It tells me more than a GPA. More than a brand-name internship where they mostly observed. It signals initiative. It signals exposure to reality.

But there's a bigger possibility here.

For some young adults, the business becomes the career. The door that wouldn't open turns out to be a door they didn't actually need.

That's not consolation.

That may be the new game.

And modern AI tools mean having a business-building coach and staff a few keystrokes away.

Wait for a calm moment — not a frustrated one. Then try this:

"I've been hearing what people like Scott Galloway and Mark Cuban are saying — that this might actually be one of the best times in history to build something because of AI. Not as a backup plan. As a real opportunity. What problem do you think you could solve for someone — even one local business — using tools you already have access to?"

Then stop. Let them think out loud.

You're not redirecting their life.

You're widening what they imagine is possible.

If they hedge, or lack confidence, try a line I used with my staff for decades: "What if we just decided to shed the constraints of what feels impossible. How about we just try it? I believe in you."

The young people I'm seeing gaining traction right now share a common trait: they made a decision and committed to it. The welder. The HVAC apprentice. The pilot in training. They're not thrashing because they stopped waiting for the system to place them — and placed themselves.

That same opportunity is available to every kid sitting at home refreshing their inbox right now.

Build something real. Use the tools that just became available to this generation and no one before it.

The market may not fix itself quickly.

But your kid's agency is available today. Right now. No one's telling them they can't just do stuff.

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🍾 To building something worth talking about,

Barry