Howdy wizards,
I’ve partnered up with Worldward, a simple product that does something quite extraordinary.
The core idea is that we remember a decision we made, but we often don’t accurately remember why we made it.
We remember the justification our mind came up with instead.
I’m so guilty of this.
When I make a decision that turns out to be the right one, my reasoning often seems obvious in retrospect. “Of course that app I made was going to go viral”.
When I make a decision and reality turns out different than I had imagined, in a way that doesn’t feel like a win, then I rationalise the other way. “There was no way I could’ve foreseen that this XYZ shitcoin I invested in was going to plummet”.
But what was I actually thinking and expecting before I made the decision?
And where do I keep making calls that are too optimistic, or pessimistic?
This is what Worldward helps you keep score of and analyse, with the help of AI.
You get into the habit of recording important decisions, with the reasoning for why you made them, and a probability you assign to them for becoming a success.
AI keeps track of your decisions, and assigns its own probability for success to each of them.
That means, later, when your mind quietly starts to edit the reason for why you made that decision, you’ll have the raw proof.
Over time, you’ll be able to see where, how, and how much you were right or wrong. And where you’re consistently too optimistic or pessimistic.
Two weeks in, here is my own record. I am more confident than Worldward on all six.
What I bet on | Me vs Worldward |
|---|---|
Luggage safe at a hotel reception | 95% vs 78% |
Password plan done by October 1 | 80% vs 73% |
Small niche partners beat big ones | 80% vs 62% |
Three demos built in two days | 75% vs 60% |
Backups run to December with no fix | 65% vs 32% |
Extra-long blog post ranks page one | 55% vs 32% |
I really like the idea of letting AI take a guess at the probability. As you’ve probably noticed—AI knows things, and it doesn’t know things.
If you track decisions consistently, my bet is you’ll develop ninja-level judgement on where AI can help you make better decisions; and just as important, where it can’t.
I wouldn’t use this for all my decisions. That’s not the point of this product.
It’s intended for decisions that are repeated, uncertain or expensive.
If I’m making a decision that matters to me, and I want to see it through and learn from it whatever the result is, tracking it makes all the sense.
With the Worldward MCP, I can log decisions right from Claude or ChatGPT:
Me: I’m publishing a blog post about twice the length I usually go for, to try to rank for a specific search term. It'll have been right if the post is on Google's first page for that term by 9 December. I give it 55% chance it will be right.
Claude: On the record. Worldward says 32%.
In a world where everyone is reaching for AI for easy answers and letting their critical thinking atrophy, tracking your judgement like this is an atomic habit.
You build discipline in reasoning about what will happen when you decide something.
You get good at showing up with a hypothesis.
And imagine in a year, when Claude has context on many of my important decisions and how they turned out versus how I thought they would. That structured context might make AI an actually useful decision partner.
If you’re interested in trying Worldward AI, you can start using it for free today.
Put a probability on an open question, save your Call, and return when the outcome can be checked. Then record a decision of your own.
❦
You are a delight.
