The Great Reversal: When the rules we’ve lived bystart to flip.

Businesses used to adapt to software. Careers were built around expertise that took years to acquire. Hard work and a good education were supposed to lead to a better life.

AI is challenging those assumptions, and we’re only beginning to understand the consequences.

Some of these changes could put extraordinary power into ordinary people’s hands. Others could fundamentally threaten the opportunities and security we’ve spent generations building.

The Great Reversal is about understanding both, and questioning who gets to decide what comes next.

The biggest story isn’t what AI can do. It’s what happens to the rest of us when the old rules stop applying.

By Jake Woodward

Technology executive. Entrepreneur. AI builder. Educator.

Read the latest essaySubscribe

Latest essay

After AI... Are You Still Playing?

If AI can do the work and make the decisions, at what point do we stop participating in our own lives?

Read the essay

“But there’s a difference between asking AI to help you play and asking AI to play for you. And I don’t necessarily think one is right and the other is wrong.”

More essays

  1. We’ve Had Software Backward for 30 YearsA small clinic just replaced a $200-a-month subscription in two weeks. That’s the start of something bigger.
All essays

I’ve spent 25 years inside the technology industry. What’s happening now is unlike anything I’ve seen.I’ve spent 25 years inside the technology industry. What’s happening now is unlike anything I’ve seen.

Jake Woodward

I’m Jake Woodward. I’ve founded businesses, led product and technology organizations, and spent most of my career building software.

Over the past two years, I’ve also spent more than 3,000 hours building with AI. Not just studying the technology, but putting it to work and seeing firsthand what it can and can’t do.

Today, I’m also a faculty member at Golisano Institute for Business & Entrepreneurship, helping prepare students for a world where the relationship between technology, business, and work is changing rapidly.

The Great Reversal is where I connect those experiences to the bigger questions I think we should all be asking.

More about Jake

The future isn’t waiting for us to figure it out.

Every week, I explore an assumption we’ve lived with for decades that’s starting to come apart.

Sometimes that’s exciting. Sometimes it’s uncomfortable. Often, it’s both.

If you’d rather understand what’s changing than be surprised by it, join me.

Subscribe to The Great Reversal