Last week I told you about failing the GMAT and feeling like a misfit. About learning that intelligence comes in forms our education system doesn’t measure or value. This week, I want to talk about Steve Jobs. But not the Steve Jobs you think you know.

In 1995, Jobs sat down for a raw, unfiltered interview that got lost for 16 years. When it finally surfaced in 2011, shortly after his death, watching it was haunting. Not because he was predicting the future. Though he was. But because he understood something most business leaders still miss.

Jobs was another misfit. Fired from his own company. Running a struggling computer business and a small animation studio that hadn’t yet proven itself. Sitting in that interview, he was 40 years old and considered a has-been.

He was also brilliantly, instinctively right about one critical thing:

You cannot innovate from inside a silo.

The Macintosh team wasn’t just engineers and programmers. Jobs deliberately hired “musicians, poets, artists, zoologists, and historians who happened to be computer scientists.” Not despite their diverse backgrounds. BECAUSE of them.

He understood that breakthrough thinking requires different minds colliding. He called it the “Rock Tumbler Theory.” Essentially, you throw in ugly, sharp rocks, add grit, turn on the motor, and they smash against each other. The friction is the point. The next day, they come out polished and beautiful.

But here’s where Jobs had a massive blind spot.

He built what he called “a bicycle for the mind” – tools that amplified human capability exponentially. He was right about that. The computer, and now AI, absolutely amplifies what we can do.

But he never questioned where we were riding that bicycle TO.

He gave us unprecedented tools without probing the systems those tools would serve. He optimized for efficiency and leverage without asking: efficiency toward what end? Leverage in service of what vision?

This is the trap we’re still living in.

Jobs also diagnosed a disease he couldn’t cure.

He explained why great companies like Xerox and IBM stopped innovating. When you achieve a monopoly, the product people can no longer move the needle. You are already winning. So power shifts to sales and marketing. Process becomes more important than content.

“People get very confused that the process is the content,” he said. “IBM has the best process people in the world. They just forgot about the content.”

What he didn’t say – maybe didn’t see – is that this is fundamentally a SILO disease. When you only have MBAs talking to MBAs, engineers talking to engineers, finance people talking to finance people – you get locked into folklore. Everyone is optimizing the same tired playbook because everyone learned from the same system.

You get extraction masquerading as innovation. You get quarterly earnings driving decisions that mortgage the future. You get the best processes in the world, building toward outcomes nobody actually examined.

This is where we are right now.

Business leaders operating in their silo, optimizing for metrics that make no sense if you step back and ask the bigger question: What are we actually building toward? Sustainability people operating in their silo, armed with data and warnings that business leaders tune out because the framing doesn’t connect to how they think. Artists and polymaths and systems thinkers relegated to the margins because our education system spent decades churning out intellectuals at the expense of visionaries.

The problems we’re facing – climate instability, economic fragility, systems designed to extract rather than regenerate – these cannot be solved from inside the silos that created them.

We need business leaders who can hear what artists see in natural patterns. We need engineers who understand what historians know about systems that collapse. We need financial minds who can integrate what poets understand about human meaning and motivation.

We need the friction. The sharp rocks tumbling against each other. The musicians in the room with the computer scientists.

Not because it’s nice. Because it’s survival.

Jobs understood that the bicycle amplifies us. He was right.

But amplification without direction is just speed toward the wrong destination.
We have more tools than ever before. More leverage. More capability. AI is handing us a rocket ship when Jobs only had a bicycle.

The question isn’t what these tools can do. The question is: What are we building? And who’s in the room when we decide?

If it’s just the people who’ve always been in the room, having the same conversations they’ve always had, using the same frameworks they’ve always used – we’re just going to get better at building the wrong things.

The misfits aren’t a nice-to-have. The diverse thinkers aren’t a DEI checkbox. The people who see the world completely and utterly different from you aren’t annoyances.

They’re how we survive what comes next.

Don’t stay in your silo. It’s the most dangerous place you can be.