A Walk With Steve Jobs

I’ve been thinking about Steve Jobs a lot lately. He’s been gone for over a decade, but right now — with social media in crisis, with GenZ 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 that 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. Jobs has always done his best thinking in motion — those legendary walks with Laurene, with Ive, with candidates he was trying to recruit to Apple. Today he’s walking with me.

“Social media is a crisis masquerading as a success story,” he says, hands animated 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.”

A group of teens passes us, heads down in their phones. Jobs stops walking.

“Look at that. Just look at that. We gave them supercomputers, and they’re using them as slot machines. That’s not their fault — that’s by design. But these kids…” He starts walking again, faster now. “They know something’s wrong. They can feel it. They’re ready for something completely different.”

“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 GenZ…” He stops at a viewpoint overlooking the valley. “They’re like the Mac users of ’84. They’re ready to throw the hammer through the screen.”

The path starts to wind downhill. Jobs seems energized now, like he’s piecing something together in real-time.

“You know what’s fascinating about GenZ? 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.”

A notification pings from one of the teens’ phones nearby. Jobs winces.

“Every ping, every notification — it’s a little theft of human potential. But here’s what gets me excited: for the first time, we have a generation that sees through it. They’re not asking for better filters or more features. They’re asking for their brains back.”

The valley’s lights are starting to twinkle on in the distance.

“The idea of doing rapid prototypes, testing with real users, that’s right. But remember: the goal isn’t to build a better social network. The goal is to build something so fundamentally different that it makes social networks obsolete.”

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.”

A teenager skates past, AirPods in, phone glowing.

“Look at that — infinite information, zero wisdom. But these kids are smart. They don’t want another app. They want meaning. Connection. Real power to create. That’s the next big opportunity.”

Jobs becomes nostalgic, remembering: “When we launched the Mac, 90% of the genius was in what we left out. But we had to build the whole thing first to know what to cut. When we made the iPhone, everyone said ‘people want keyboards.’ No. People want magic.”

Our conversation shifts to the present day. Jobs stops at a bench, he wrinkles his brow as we discuss the growing concerns about children and technology. After a moment, he speaks.

“When Lisa was young, I saw this pattern. 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 is now glowing with shapes and forms.

“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.”

His voice gets fiercer. “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.”

“No.” Jobs is emphatic. “But banning them isn’t the answer either. What’s in schools now is chaos — kids switching between TikTok and assignments, their attention shredded.”

He’s becoming more animated, shifting from nostalgia to thinking about the future. “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? That’s lazy thinking.”

“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?’”

“That’s the ultimate irony.” Jobs shakes his head, almost amused. “Apple created tools for creativity, for learning, for human potential. But somewhere along the way, these devices became delivery mechanisms for social media dopamine hits.”

He stops walking. “The iPhone was meant to be a bicycle for the mind. Now people are treating it like digital fentanyl. That’s not Apple’s fault directly, but…”

He pauses. “We didn’t see this coming. We didn’t build enough guardrails.”

“But banning Apple products from schools? That’s missing the point entirely. 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.”

Jobs leans against a tree, moonlight catching his profile.

“Tim’s brilliant. But this isn’t an engineering problem. Look at Ping — Apple had the engineers, had the resources. Failed completely. Why? Because social connection isn’t about perfect code or beautiful interfaces.”

He straightens up. “Apple excels at contained experiences. Control every pixel, every interaction. But true social platforms? They’re chaos. They’re messy. They evolve in unexpected ways. That’s not Apple’s DNA.”

“The business model question — that’s where everyone gets stuck,” Jobs says, walking faster. “They think it’s binary: either harvest attention for ads, or charge subscriptions. The companies winning the ad business today? They’re strip-mining human attention. There’s no long-term future in that. None.”

You may have noticed, I’ve stopped asking questions. Jobs doesn’t need an interlocutor; he’s his own best internal interrogator.

“These social platforms? They’re leaving money on the table. The real opportunity isn’t in selling ads against anxiety. It’s in creating spaces where genuine value can emerge.”

And now he’s looking around corners. “Look at the creator economy — it’s trapped inside these attention casinos. What if instead of optimizing for engagement, you optimized for creative output? For genuine connection? For actual human flourishing?”

His eyes narrow. “The money follows meaning. Always has. Build something meaningful enough, and the business model becomes obvious.”

“The business model of the future?” Jobs gestures to the valley below. “It’s not about monetizing eyeballs. It’s about monetizing transformation. To do that, you need three clear steps.”

We’ve gone past our planned time, walked around the building twice, and now it’s dark, but Jobs wants to leave me with advice, more like marching orders.

“First: Speed. Not rushing, but velocity with direction. Every week spent building the wrong thing is a week young minds stay trapped.

Second: Standards. Your platform has to be insanely great from day one. The first hundred users will determine if you get the next million.

Third: Soul. The soul of this project isn’t technology — it’s liberation. Every decision, every feature, every line of code has to serve that mission.”

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.”

“Make it worthy of them.”

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

Jobs pauses in the moonlight, 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 your real mission. Not building a better social network. 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 2017. Given the massive impact Job’s has had on my career and life, I tried to be honest about his concerns and ideas at this critical moment in tech history.