Thinking with AI · Coming soon
Remember why you made the call, before hindsight rewrites it
Once you know how a decision turned out, you cannot recall what you believed when you made it. This course gives you a short decision record you fill in before you commit, an AI partner that argues the other side, and a review routine that compares the record with what happened.
The course: A decision journal with an AI partner
$15 $29 early-bird price
This course is being built now. Join the early-access list to reserve the early-bird price and shape what it covers.
The course is still being built. Joining the list is free, and you pay only if you buy at launch, at the early-bird price.
If this sounds like your week
- A decision turns out well or badly and you judge it by the result, because you no longer know what you knew at the time.
- You make the same kind of mistake twice and only notice the pattern afterwards.
- Nobody around you pushes back before a big call, so your first reasoning goes unchallenged.
- You started a decision journal once and it became a chore you stopped after a few entries.
What you do now, and where it stops working
Today your past decisions live in memory, scattered notes or nowhere. Memory edits the story after the outcome, so the lesson you draw is often from the result and not from the reasoning.
What changes after the course
- Each important decision has a record, written before you commit, of the options, your reasoning, what you expect and how confident you are.
- Before you commit, you have read the strongest case against your choice.
- On a set schedule you compare each record with the outcome and mark whether the reasoning or the luck drove it.
- After a few months your records show the kinds of decision where you tend to be overconfident.
How it works: Record, challenge, review
- 1Record: fill in a one-page template before you commit — the decision, the options, your reasoning, the expected outcome and your confidence.
- 2Challenge: give the record to an AI partner with a prompt that argues against your choice and names what would change your mind.
- 3Commit: note what you changed, if anything, and decide.
- 4Review: when the outcome arrives, compare it with the record and separate decision quality from result.
- 5Look for patterns: every quarter, read your reviews together and write down one rule you will apply next time.
What you get
- Decision record template for Obsidian, Notion or plain text
- AI challenge prompt set
- Outcome review template and schedule
- Video walkthrough of a decision from record to review
This is for you if
- You make a handful of decisions a year where money, people or your career are on the line.
- You have read about decision journals and want one you will keep using.
- You want someone to argue with your reasoning before the decision, not after.
Skip it if
- You want an AI to make decisions for you. Here it challenges you; you decide.
- Your decisions are small and frequent. The record is meant for the few that matter.
- You want a lesson within a week. Reviews arrive when outcomes do, which can take months.
Before you join
- I do not have time to journal.
- This is not a daily journal. You write a record only for the decisions that matter, and the template fits on one page. Most of the work happens at review time, on a schedule you set.
- I tried a decision journal and stopped. Why would this one last?
- Journals usually lapse because reviewing them feels like a chore with no reward. The course puts the review on a schedule, keeps each entry short, and adds a partner that argues back, which gives the entry a use on the day you write it.
- Will the AI just agree with me?
- By default, models tend to agree with the person asking. The challenge prompts in the course tell the AI to argue the opposite case and list what would prove you wrong, and the course shows you how to tell when it has slipped back into agreeing.
- Can I put sensitive company decisions into an AI?
- You choose what goes in. The template works in plain text, Notion or Obsidian without any AI, and the course shows how to remove names and figures before the challenge step. Use whichever AI tool your employer allows.
- Who wrote this?
- Jay West writes How to Think at howtothink.ai, a curriculum on thinking where each lesson carries an exercise, a failure mode and a step into your week. This course applies that format to the decisions you make at work.
Rather have it built for you? Describe the project and the same work can be done for your team.