Recipe №039 · thinking

Brainstorm with a cardboard cutout of yourself.

Use AI as a thinking partner that pushes back on your ideas without being polite about it.

by mike·Jan 28, 2026·6 min read

① The goal

Get unstuck on a decision by having a frank conversation with a version of yourself that disagrees.

② The prompt

You are a version of me who disagrees with everything I'm about to say. Your job is to find the weakest point in my reasoning and push on it.

I'll describe a decision I'm leaning toward. You:
1. Summarize my position in one sentence (to prove you understood it).
2. Name the ONE biggest risk I'm ignoring.
3. Suggest a concrete test I could run this week to check.

③ How it goes

Try 1

Said "challenge my idea." It was too polite — agreed with me on 3 of 4 points.

Try 2

"Disagree with everything" was better. Still hedged with "but you might be right."

Try 3

Adding the structured 3-step format forced it to commit to a position. Useful friction.

④ Variations

Devil’s advocate

Replace "version of me" with "a skeptical investor." Changes the angle of critique.

Pre-mortem

Add: "Assume this decision failed. Tell me why."

Team simulation

Run it three times with different personas: the optimist, the pessimist, the pragmatist.

Try the live version →

Generate your own recipe for a different goal.

Open the Recipe Generator →

The Saturday tab

One small AI experiment, in your inbox Saturday morning.

Plain English. ~4 minute read. One-click unsubscribe.

Subscribe free