Look what I learned this week…
For the last few years, I’ve been leaning further and further into the “human” side of things.
The more AI takes over, the more valuable the human side of thing of things will become.
I found the map that does a great job of reinforcing that.
It’s called the “AI Proof Quadrant” (credit to Perry Marshall via his monthly print newsletter).
I sketched it out in my notebook last weekend. It validated everything we’ve been talking about here at Redefining Retirement.
If you’re still clinging to the old rules of the workplace – efficiency, speed, predictable results – you might want to reconsider.

The “AI Kill Zone”
Here’s what my chicken scratched sketch is saying about the economic reality we are facing.
Top Left (Unproductive & Predictable): Bureaucracy. Middle management. Admin. AI takes this easily.
Bottom Left (Productive & Predictable): Coding. Data entry. Logistics. AI takes this.
Bottom Right (Productive & Unpredictable): Strategy optimization. Agentic AI is eating this sector faster than we thought.
If your income relies on being “productive” or “predictable,” you are in the kill zone. The robots are, or will be, cheaper than you.
The Human (Celebration) Zone
That leaves the Top Right corner: Unproductive & Unpredictable.
Corporate culture hates this zone. It looks like waste it’s messy. But for us, it is the only safe harbor even though it may not feel right.
Here are the six traits Perry listed that define this zone. Algorithms struggle to replicate these:
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Analog: Not online. Real paper, real handshakes.
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Artistic: Creative work that doesn’t follow a template.
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Altruistic: Doing things without a calculated ROI.
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Subversive: Thinking like an outsider.
Subversive is the one intrigued me the most.
But I had look it up to really get a handle on it…
The “Subversive” Mindset
To stay AI proof in your career or business, you have to break the rules. AI is the rules.
Here’s the checklist of what I found on how to create a subversive mindset::
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Question Everything. Shouldn’t be a problem for us cynical Gen Xers.
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Think Like a Supervillain. Look for the edges of the system.
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Embrace Disagreeable Thinking. If everyone agrees with your idea, it is predictable.
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Understand the System. You have to know how it works to subvert it.
We aren’t trying to out-churn the AI with more content. We are going the other way. We are building something messy and human.
Here’s how you can work on that…
AI Exercise: The “Rory Sutherland” School of Anti-Logic
Who is Rory Sutherland? He is the Vice Chairman of Ogilvy and the author of Alchemy. He is a master of the “Unproductive/Unpredictable” quadrant.
Why he matters: Rory argues that the modern world is obsessed with logic, but humans aren’t logical. We are psychological.
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Logic says: Make the train faster to increase satisfaction. (Costs $6 billion).
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Alchemy says: Put WiFi on the train so people enjoy the wait. (Costs $50 million).
If you rely solely on data (The “Productive” zones), you miss the magic. You need to learn “Psycho-logic.”
Step 1: The Education Prompt Before you apply this to your career or business, let the AI teach you the framework. Copy/paste this to understand the “Subversive” mindset.
