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As heard at the Section AI “Future of Work” event, hosted by CEO Greg Shove
By Michael Penwarden

For decades, Gen X was the Jan Brady of the workforce—sandwiched between boomer dominance and millennial disruption, playing it cool while everyone else got the spotlight and the think pieces.

But here’s the plot twist nobody saw coming: the overlooked middle child of modern work may be the most perfectly positioned generation to own the AI revolution.

At the recent Section AI: Future of Work event, two voices cut through the noise with startling clarity: Jaime Teevan, Microsoft’s Chief Scientist, and Scott Galloway, NYU professor and serial entrepreneur. Together, they revealed why Gen X’s peculiar blend of analog wisdom and digital fluency isn’t just relevant—it’s essential.

They Lived Both Worlds

Gen X was the last generation to grow up pre-digital, which means they know how to read a room, run a meeting, and handle difficult people without melting down in Slack. But they also rode the first internet wave, survived the dot-com crash, and adapted to mobile before it was mandatory.

Unlike some boomers, they’re not intimidated by technology.
Unlike younger workers, they’re not enslaved by it.

“This transition requires more than tech skills,” Teevan observed.
“It demands metacognition—thinking about how you think, and asking better questions.”

Gen X has the perfect distance: close enough to technology to master it, far enough to question it.

They’re Flying at the Right Altitude

Gen Xers are now managers, directors, VPs. They’re senior enough to shape strategy but not so entrenched that they fear change.

They’re not junior devs watching their jobs get automated.
They’re not fresh MBAs wondering why consulting offers are disappearing.

They occupy the Goldilocks zone: experienced, adaptable, and empowered.

“Mid-level managers are the ones who can use AI as a mentor,” Galloway noted.
“Upload your work history. Ask if your boss is invested in your success. Benchmark your value. No one’s going to do it for you.”

Gen X learned long ago that nobody was coming to save them.
That’s exactly why they’re ready.

They Remember Life Without a Co-Pilot

Here’s the paradox: AI is most valuable to those who don’t depend on it completely.

Teevan described the coming shift not as replacement, but reorientation:

From executing tasks to integrating systems
From production to orchestration

Orchestration? That’s Gen X DNA.
They’ve been project-managing chaos since they were latchkey kids coordinating their own afterschool lives.

They don’t expect AI to do the work for them.
They expect it to amplify their capabilities—and they know how to direct that power.

They’re Disillusioned in Exactly the Right Way

Gen X never bought the “company as family” mythology.
They came of age during mass layoffs, economic crashes, and the death of pensions.

They understand that corporations will eliminate 20% of staff while issuing press releases about “innovation and efficiency.”

That realism isn’t cynicism—it’s operational intelligence.

“CEOs are quietly asking how to extract 20–30% more productivity with fewer people,” Galloway revealed.
“They’re not buying ‘augmentation.’ They’re buying ‘replacement.’”

Gen X isn’t shocked by this revelation.
They’re already sharpening their tools.

They Still Insist on Being Human

In a conversation that spiraled into reflections on isolation, digital addiction, and algorithmic manipulation, Galloway’s sharpest warning wasn’t about job displacement—it was about human displacement.

“AI is creating a generation of young people who are anxious, disconnected, and substituting simulation for authentic experience,” he said.

Gen X recognizes the danger because they remember the alternative.

Mixtapes
Face-to-face confrontations
Road trips without GPS
Jobs landed through actual conversations

They’re not nostalgic—they’re grounded.
And they might be the essential bridge between a hyper-digitized future and a meaningful one.

This Is What Gen X Was Built For

Forget the apocalyptic AI narratives. The opportunity is massive—but it’s uneven.

Those who can communicate, integrate systems, and lead humans working alongside machines will dominate.

And for once, Gen X has perfect timing.

No viral campaigns
No performative disruption
Just quiet, competent revolution

So to every Gen Xer reading this:
You’ve been waiting in the wings long enough.
Now take the helm and set sail.