Taking A Walk With Steve Jobs

I’ve been thinking about Steve Jobs a lot lately. I rewatched the documentaries and dug back into Isaacson’s book. None of them quite captured it all, but they helped me frame the conversation I wanted to have with him.

He’s been gone for over a decade, but right now, with social media in crisis, with Gen Z demanding change, I kept wondering: What would Jobs see in this moment?

So I invited him for a walk.

Jobs arrives, characteristic black turtleneck, that intense focus, as we stroll around the pebble path of Apple Park, which loops around the Norman Foster building that opened in 2017.

Rosenbaum: Thank you for doing this. I’ve been obsessing about social media lately…

Jobs: (sharp glance)You mean that digital wasteland that’s eating our kids’ minds?

Rosenbaum: Exactly. And I keep thinking: You saw around corners. You saw the Mac when others saw command lines. The iPhone, when others saw keypads. What do you see now?

Jobs: (pauses, considering)You know what everyone gets wrong about innovation? They think it’s about technology. It’s not. It’s about human beings — what they need before they know they need it.

The late afternoon light is hitting Silicon Valley just right as we walk.

“Social media is a crisis masquerading as a success story,” he says as we climb a slight incline. “But everyone’s looking at it wrong.”

I wait. With Jobs, silence often yields more than questions.

“When we made the Mac, we didn’t start by asking how to make computers better. We asked how to unleash human creativity. The problem isn’t social media — it’s that we’ve built digital cages and called them communities.”

“You have to understand,” he continues as we round a corner, “when we launched the iPhone, carriers thought they owned the customer relationship.” (Scoffs.) “We broke that model because it was broken. Social media today? Same thing.”

The sun’s getting lower now. Jobs walks in silence for a moment, processing.

“These platforms — Facebook, Instagram, TikTok — they think they own human connection. They’ve monetized anxiety and called it engagement. But you know what’s fascinating about Gen Z? They don’t just want better tools — they want better outcomes.

“When we built the iPhone, we had this phrase: ‘the intersection of technology and liberal arts.’ That’s what’s missing from social media.”

Jobs picks up his pace as the last light fades.

“When we designed the original Mac interface, we obsessed over every pixel. Not because pixels matter, but because human attention is sacred. These social platforms? They treat attention like currency to be strip-mined.

“When we made the iPhone, everyone said ‘People want keyboards.’ No. People want magic.”

Our conversation shifts to the present day. “Parents want a simple fix. But there’s nothing simple about this. The real issue isn’t phones in schools. It’s what these platforms do to developing brains. We didn’t give kids cigarettes in schools, but banning smoking wasn’t what solved the problem. Education did. Regulation did. Creating better alternatives did.”

The growing dusk descends, and Apple’s circular building glows.

“These kids need digital literacy more than they need digital abstinence. When we put Apple computers in schools, we weren’t just adding technology — we were teaching creative empowerment. That’s what’s missing now.

“But here’s what parents are right about: their kids are being harmed. They just don’t understand that taking away phones without providing better alternatives is like taking away cars without building public transit.”

Now he’s brainstorming solutions. “Schools need clear frameworks. Maybe phones are locked during class, unlocked during breaks. Maybe they’re tools for specific learning moments. But this all-or-nothing approach? Remember when schools banned calculators? Same panic, wrong problem. The real question isn’t ‘phones or no phones.’ It’s ‘How do we teach these kids to be masters of technology, not slaves to it?’

“The problem isn’t the hardware. It’s what runs on it. These social platforms turned our devices from tools of creation into tools of consumption.

“You want to fix education? Give kids devices loaded with creative tools, but locked down from social media during school hours. Simple. Clear. Enforceable.”

He turns to face me directly. “When we launched the Mac, that first ‘Hello’ changed everything. Your moment is bigger. These kids don’t just need a new platform. They need their minds back.”

He starts walking away, then stops. “And remember: Stay hungry, stay foolish. But most importantly… stay human.”

Jobs pauses in the moonlight and turns back one last time.

“You know what the iPad was originally called? The Safari Pad. Because we thought web browsing was the killer app. We were wrong. It became something entirely different: a canvas for human creativity.

“That’s the real mission. Not building a better social network, but building a canvas for human connection, for genuine growth. For digital liberation.

“The world’s ready. These kids are ready.”

This walk is metaphorical, as no one can know what Jobs would have said or done given the changes in tech since the iPhone launched in 2007. But given the massive impact Jobs has had on me and the world, I tried to be honest about what I think his concerns would be at this critical moment in tech history.