Morning, CEO!
Let’s talk about the absolute worst way to fall asleep: Trying really, really hard to fall asleep.
You lay there. You command your brain to shut down. You scream “RELAX!” internally at your own eyelids.
And the result? You are wide awake, staring at the ceiling, calculating how many hours of misery remain until your alarm goes off.
This isn’t just you being bad at sleeping. It’s a cognitive glitch that ancient Chinese philosophers were trying to debug 2,000 years before melatonin gummies existed.
Today, we’re looking at Edward Slingerland’s book Trying Not to Try. It’s not about doing nothing. It’s about how to stop strangling your own success.
1. The “Try-Hard” Problem
We all know that person at the networking event.
They are making perfect eye contact. Their handshake is calibrated to the exact millinewton of pressure. They have a rehearsed anecdote about “synergy.”
And they are completely terrifying.
Why? Because they are “trying.” You can smell the effort.
In ancient China, the goal was Wu-Wei (effortless action). Think of a jazz pianist improvising or a butcher slicing meat without looking. They aren’t lazy; they are in a state where high skill meets zero conscious effort.
Here is the science part (because I need charts to understand feelings):
We have two systems. System 1 (Hot) is fast and automatic. System 2 (Cold) is slow and controlling.
Most of us spend our careers letting System 2 bully System 1. We have a “Smoke Alarm” in our brain scanning for errors, and a “Firefighter” trying to fix them. When both are running, you are awkward. You are slow. You are the person calculating how to be funny instead of just being funny.
I used to think being a professional meant keeping the Firefighter awake 24/7. But true mastery—whether in strategy or coding—happens when you shut the Firefighter up.
You have to try very hard (training) so that you can eventually stop trying (mastery).
2. Why Your “Vibe” is an Asset
Let’s talk about your “De.”
No, not the thing you get on a report card. In early Chinese thought, De translates to “Virtue,” but it’s actually more like “Charismatic Power.”
It is the superpower of Wu-Wei.
When you stop micro-managing your own personality (System 2) and let your trained instincts (System 1) take over, people trust you.
Think about a politician reading a teleprompter. Every hand gesture is scripted. You don’t trust them. They have zero De.
Now think of the leader who goes off-script, maybe stumbles a word, but speaks from the gut. You follow them into battle. They have massive De.
As you build your own enterprise, remember this: Artificial Intelligence is pure System 2. It is pure calculation. It has zero De.
Your clients and bosses aren’t hiring you just for the output; they are hiring you for the judgment that comes from your Hot Cognition.
If you try to act like a computer—perfectly logical, emotionless, rigid—you are competing with AI on its home turf. You will lose.
Your competitive advantage is your ability to be effortlessly, spontaneously human.
3. Four Ways to shut up the “Firefighter”
So, how do we actually achieve this “effortless” state without just taking a nap?
The book outlines four ancient philosophers who are basically the Board of Directors for your brain. They all want Wu-Wei, but they argue about how to get there.
Director 1: Confucius (The Grinder)
The Strategy: Fake it ‘til you make it.
The Vibe: Carving rotten wood into a statue.
Use when: You are learning a new skill. You force the habits. You memorize the scripts. You grind until the unnatural becomes natural.
Director 2: Laozi (The Minimalist)
The Strategy: Unlearn everything.
The Vibe: Return to being a baby.
Use when: You are over-thinking. Stop reading business books. Stop optimizing your calendar. Just sit there. Trust your gut.
Director 3: Mencius (The Gardener)
The Strategy: Nurture the “sprouts.”
The Vibe: You are already good; just add water.
Use when: You feel a spark of excitement. Don’t force it (Confucius) or ignore it (Laozi). Just gently encourage the natural inclination.
Director 4: Zhuangzi (The Surfer)
The Strategy: Lose your mind to find it.
The Vibe: Ecstatic flow.
Use when: You are in the crisis zone. Forget “good” and “bad.” Forget the outcome. Just ride the wave.
I used to only listen to Confucius. I thought suffering was the only path to value. Now, I try to rotate the Board members depending on the problem.
The Punchline
We are trained to believe that “Agency” means “Control.”
But the highest level of agency is actually Trust.
Trusting the years of experience you’ve banked. Trusting your gut over your spreadsheet. Trusting that if you stop strangling the steering wheel, the car will drive smoother.
Stop trying so hard to be the CEO. Just be the one who knows where the ship is going.
Links:
https://www.edwardslingerland.com
https://www.amazon.com/Trying-Not-Try-Science-Spontaneity/dp/0770437613
