Why "optimized thinking" won't work in the AI era
The optimization era turned our minds into compliance departments that avoid mistakes. The AI era needs a different kind of thinking.
Over the past few weeks, I’ve been listening to ideas on where to take this newsletter.
(Thank you to all who took the time to respond!)
The majority said:
I want to learn how to think more deeply.
So I’ll be upfront.
I think most current “deep thinking” advice isn’t preparing us for the future…
My obsession with mental models
For years, I assumed “thinking deeper” just meant having a better decision-making toolkit.
I became obsessed with “mental models” (essentially logical frameworks and formulas).
You’ve likely seen the cheat sheets online.
They promise to help you eliminate bias, minimize loss, and stop you from making “dumb” mistakes.
I collected these frameworks like insurance policies.
I thought if I had enough of them, I’d finally feel like a confident, grounded thinker.
Instead, a weird thing happened.
I became more anxious, not less.
I stopped looking for breakthroughs and started looking for “errors” everywhere.
I wasn’t building a unique vision; I was just auditing my every move to make sure I wasn’t being “stupid.”
My mind became a compliance department for my life.
It took me a long time to realize that these tools weren’t the problem.
They were symptoms of the incentive system we're in.
Why thinking became defensive
Every era rewards a particular style of thinking.
The Greeks looked for virtue. The Renaissance looked for beauty. The Industrial Age looked for efficiency.
During periods when authority is centralized and mistakes are punished, thinking inevitably becomes cautious.
That's what happened in the Middle Ages, and I think we're in a modern replay of it.
Back then, the Catholic Church held immense power.
Even the most brilliant theologians had to work within a mental fence: “Will this thought be approved by the Church?”
There was always a compliance process running in the background.
Today, the authority isn’t religious, but economic.
We live under the Church of Optimization.
Under this power, mistakes are punished during performance reviews, and every choice must be “de-risked.”
This is why we naturally reach for tools that help us play defense.
We don't ask, “What is worth building?”
We ask, “What’s the most optimized move?”
Like the theologians of the past, we're thinking deeply.
But it’s all in service of defensive thinking.
We use our mental toolkits like shields to protect us from the “sin” of an unproductive hour or a “wrong” choice.
The AI era: Why optimization is a dead end
We're not just burned out from stress or being overworked.
We're going through an intellectual burnout of concentrating all our mental power on thinking like machines.
This is why people are taking the leap and starting over in their 30s, 40s, and 50s to step off the “logical path”.
Others feel empty and directionless even though they’ve made all the “right” choices.
The goals are shifting towards: Meaning over mere productivity, alignment over “safety” defined by others, and curiosity without obsessing over ROI.
Many of us are feeling a disconnect with our minds and where we want to go.
The mental toolkit we’ve been building helps us stay within the “safe compliance zone”, when we want something beyond that.
And this isn't just about what we want.
We need to think about the changing needs in the new age we're living in.
In the AI era, LLMs can generate every possible scenario better than you, but they can't create your vision.
The human thinking that becomes valuable is your unique perspective and seeing outside the "safe" logic of our time.
Defensive thinking isn't going to help you do that.
From defensive to expansive thinking
So at this point, people often think “So what? Am I supposed to just start doing risky stuff?”
Well, not quite either.
The history makers and visionaries aren’t reckless contrarians who enjoy risk for the heck of it.
They do stuff that only appears stupid to the masses because they operate at a different thinking level.
It’s not because they ignore consequences, but because they stay with questions others aren’t willing to sit with.
Most of us use mental models like insurance policies, constantly asking: “Is this a practical, risk-minimizing decision?”
Great minds use them as levers to stretch what’s possible: “What is the truest version of my vision, and how do I build around it?”
This is the leap from defensive to expansive thinking.
It's where you stop building a shield and start building your truth.
In the AI era, being an “optimized” thinker means you're competing with machines.
Expansive thinking allows you to operate at the level of visionaries.
Cultivating it isn't a matter of luck; it requires a new set of mental practices:
Honing taste: Developing the "aesthetic eye" needed to identify truly great ideas in a sea of generic AI sameness.
Defining your theory of everything: Connecting ideas into a coherent, signature worldview only you can see.
Pursuing the “useless”: Building an “unpromptable” foundation of curiosities that make you irreplaceable.
Sitting with the mess: Learning to stay in uncertainty until a unique solution emerges, instead of grabbing the first “safe” answer to stop the anxiety.
Life as a lab: Shifting from “auditing errors” to “running experiments”.
Setting the tone for the year
For the rest of the year, this is where the Thinking Arc is headed.
If you’re looking for more thinking tools to help you play it safe, you probably won’t find them here.
But if you’re ready to stop managing your potential and start expanding it, I hope you’ll stay.
We’re going to stop treating our minds like calculators for risk and start treating them like instruments for orientation and vision.
I’m looking forward to thinking together.
— Dawn
P.S. FREE essays will stay the same (they're just moving to Tuesdays).
P.P.S On January 29, I’m opening a dedicated space for those who want to move from theory to application and develop this kind of thinking more deliberately. I’ll share more next week.
Defensive thinking is rooted in trauma and fear. How can you force a person to think when they are afraid and don't even understand the source of that fear? That is, if they even realize what’s troubling them at all. Isn't this a form of self-violence? Shouldn't we focus on healing first, in order to truly perceive reality and hear our own inner voice?
However, while expansive thinking can transcend optimization by delving into the great unknown for ideas, that great unknown is full of risks. People who are able to become visionaries are usually people with strong safety nets where they can afford to take risks (i.e. drop out of college, start a company), or people with nothing left to lose (which is why violent revolutions tend to occur as a result of a critical mass of the desperately poor).
If you have just enough safety net to be stable, but not enough to cushion an emergency fall without losing a significant amount of key resources (house, car, job, family, etc.), you will be incentivized to avoid risk and think as defensively as possible to prevent loss. This is why it's usually the poor and the rich that think expansively and try crazy things, while the working and middle classes think very defensively on survival and securing their wealth from loss.