By Michael Penwarden

The old rules are dead. Here’s how to write the new ones.

This piece emerged from insights gathered at “AI and the Future of Work,” an event hosted by Greg Shove of Section, where leading voices in technology and business shared their unvarnished views on what’s really coming.

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The storm is here

(See “Young Graduates Are Facing an Employment Crisis”)

While you’ve been cramming for finals, the world outside has been quietly dismantling everything us “adults” have told you about your careers.

• The corporate ladder? Sawed off at the bottom.
• Entry-level positions? Automated away.
• The safe harbor of a steady job? There is no harbor anymore—only open ocean.

You’re smart. That’s good. But intelligence without direction is just expensive drift.

The machines are coming for the predictable work—the template-filling, the answer-generating.

What they can’t touch—what they’ll never touch—is the raw human genius of:

• seeing connections others miss
• asking questions that haven’t been asked
• walking into a room and changing the weather

This is your map through the chaos.

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The Metacognitive Gambit

“AI increases the metacognitive demand of what we do.”
— Jaime Teevan, Chief Scientist at Microsoft

Translation: The valuable work isn’t producing answers anymore. It’s asking better questions.

We’re entering what she calls the “metacognitive era”—a time when thinking about thinking becomes the ultimate competitive advantage.

While others are trying to outpace machines at their own game, you’ll be playing an entirely different sport.

Memorizing facts is dead work.
Building things is table stakes.

The real game is integration—seeing patterns across disciplines, questioning systems, thinking in three dimensions while others are still drawing straight lines.

Your move:

• Study philosophy alongside data science
• Read Camus and Kafka
• Practice explaining quantum physics to your grandmother, then her wisdom to a physicist

The future belongs to translators, not just specialists.

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The Human Frequency

“Nothing wonderful is going to happen to you on a screen.”
— Scott Galloway

Galloway makes his kids talk to a stranger before they’re allowed back in the house. It sounds harsh—until you realize he’s teaching them the most valuable skill in an AI world:

Being irreplaceably human.

While your peers are perfecting their LinkedIn profiles, you should be perfecting your handshake.
While they’re optimizing their résumés, you should be optimizing your presence.

Charm, clarity, and courage compound like interest.

In a world where AI can write your pitch deck, your edge is being the person who can:

• deliver it with conviction
• adapt it on the fly
• connect with the human across the table

Your move:

• Join the debate team
• Start a podcast
• Learn improv
• Practice public speaking until your voice carries authority

Stories move markets—learn to tell them well.

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The AI Sparring Partner

Here’s what the career counselors won’t tell you: AI isn’t your competition. It’s your training partner.

• Teevan calls AI a “thought partner”
• Galloway calls it a mentor, a truth-teller, a brutal benchmark

“Ask your AI: Am I about to get laid off? Am I actually learning here? Does my boss seem invested in me?”

But here’s the trap: offloading your cognition to AI is like letting GPS do all your navigation.

You’ll get there, but you’ll never learn the territory.
You’ll become a passenger in your own career.

The winners use AI like a mirror—to sharpen their thinking, not replace it.

They:

• run two models against each other
• compare insights
• feed their work back through the machine to find blind spots

They don’t just prompt—they spar.

Your move:

• Use LLMs to critique your ideas, not generate them
• Write something, then ask AI how to make it better
• Run the same question through different models and compare

Make the machine your intellectual sparring partner—not your ghostwriter.

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The Proximity Principle

Remote work is seductive. It’s also a career killer.

“Get into the office. Bounce off people.” — Galloway

The ambitious young professional who thinks they can build a career from their bedroom is making a catastrophic miscalculation.

Mentorship happens in margins—the hallway conversation, the coffee run, the “Hey, what are you working on?”

These moments don’t translate to Zoom.
They can’t be scheduled or optimized.
They require presence, proximity, and alchemy.

The future belongs to those who show up.

Your move:

• Take the job that puts you in the room with smart people
• Move to the city where things happen
• Volunteer at events
• Sit at the bar, not behind the screen
• Pay your dues with presence

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The Navigator’s Mindset

The old career advice is worse than useless—it’s dangerous.

There is no ladder anymore. There are no guaranteed paths. The maps are all wrong.

But here’s what they don’t tell you:

The ocean of opportunity has never been wider.

You’re not just a student collecting credentials. You’re a navigator charting unknown waters.

The greatest skill isn’t mastering a tool—it’s being able to reframe your value in a world that’s rewriting itself daily.

“There’s a capability overhang,” Teevan notes.
The tools are ahead of us.

The question isn’t whether you can keep up with tech.
It’s whether you can keep up with the possibilities it creates.

Your move:

• Build your own compass
• Know your values, but hold tactics lightly
• Learn to sell ideas, not just execute them
• Follow your curiosity across disciplines
• Trust your instincts, but verify with data
• Most importantly: keep moving

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The Choice

This is the best time in history to be highly intelligent—if you’re brave enough to be human about it.

AI will make:

• the top 10% unstoppable
• the bottom 90% invisible

It will amplify genius and automate mediocrity.

The question isn’t whether this is fair—
It’s which side you choose to be on.

The future belongs not to those who can compete with machines,
But to those who make machines irrelevant:

• Not by being faster
• Not by being more accurate
• But by being more human
• More curious
• More connected
• More alive to possibility

So use the tools, but don’t become one.
Build systems, but don’t become systematic.
Optimize for efficiency, but never at the cost of serendipity.

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Final Word

The old world is ending. The new one is beginning.

And you—brilliant, restless, ready—you get to help write it.

Now go make it happen.