Issue 031
Fall In Love With Good Iterations
February 5, 2026
What if the fear of making mistakes is the actual mistake?
For years, I tried to avoid mistakes by over-analysing all my decisions and perpetually planning.
I thought I was being careful, but all that caution didn’t make me better. It just made me slower, more anxious, and trapped in a prison of my own making.
The breakthrough came when I realized mistakes aren’t the problem. They are the solution.
Here’s the thing: mistakes are inevitable because you don’t know what you don’t know.
We all operate in the world using our misconcepts - mental models of the world that are inherently fallible and incomplete. If our understanding of the world is always a work in progress, then a "mistake" is simply necessary information. It reveals exactly where our model needs error-correction.
“All models are wrong. Some are useful.” - George E P Box
Once I saw mistakes this way, everything changed.
The question was no longer “How do I avoid mistakes?”
It became “How do I iterate faster?”
Think of iteration as a learning loop:
- Decision: Made based on your current misconcepts
- Action: Decisions implemented in the world
- Feedback: Real-world results of the action
- Update: Use the feedback for error-correction
- Repeat: Make a better decision using your updated misconcepts
The faster you cycle through this, the faster you improve.

I used to think I needed to be right. Now, I just want to get better because I know I can’t always be right.
The fear of making mistakes keeps you stuck.
But iterations? They compound. Every cycle makes you a bit sharper, a bit wiser, a bit freer.
I’m still practicing this, and honestly, some days it’s still hard to fail. But I’m falling in love with good iterations because it’s the only way forward.
Making the Change
Here's my question for you: Where are you currently stuck because you’re afraid to be wrong? What would just one iteration look like?
Start there. Try. Fail. Learn. Iterate.
If this was useful, the next one will be too.
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