THE
SCEPTIC’S
DESK
AI Trading, Demystified
Starter Pack
Edition 2026 · v1.0
Five prompts + one bonus

The Sceptic’s Starter Pack

“Better questions create better traders.”

The prompts from your Starter Pack, ready to copy on whatever device you have to hand. Each one asks an AI to argue with you at a different stage: your belief, your strategy, your backtest, your size, and your record.

Before you paste

Swap anything in [square brackets] for your own detail. The more specific you are, the less generic the answer.

These work in any assistant. Every answer is a draft, not a fact: check numbers, quotes, and code against a real source before you act on them.

The five

Your belief

Why would a pro disagree?

Learning & understanding

I believe [a trading belief I hold]. Give me the strongest case an experienced trader would make against it, and what evidence would tell me I’m wrong.

#5 in the full Vault
Your strategy

Devil’s advocate

Strategy building

Argue as hard as you can against this strategy. In what conditions does it lose? Worst realistic losing streak? Hidden costs? Is it fitted to a story, or is there a real reason it works? Be blunt. [strategy]

#14 in the full Vault
Your backtest

Overfitting audit

Backtesting

Assume I’ve fooled myself. Find signs of overfitting or unrealistic assumptions in this backtest, and tell me how to test it out-of-sample. Be sceptical. [paste results + rules]

#26 in the full Vault
Your size

Position size

Risk & sizing

My account is [amount] and I risk 1% per trade. I want to [buy/sell] [instrument] at [entry] with a stop at [stop]. Work out cash at risk, stop distance, and exact size. Show the steps and state your assumptions.

#31 in the full Vault
Your record

Journal review

Review & psychology

Act as a blunt, experienced trading coach. From this journal, find where I make versus lose money, whether I follow my own rules, any emotional patterns, and my single highest-impact fix for next month. Use my real numbers. Don’t flatter me. [paste journal]

#37 in the full Vault

The bonus

Bonus

Macro calendar read · live web

Research & news

[paste context block] Give me this week’s scheduled data and events for my markets that could cause volatility, ranked by likely impact. Cite sources. End with ‘what could make this read wrong’.

Needs an AI with live web access, and it asks for sources. Check two of them before you let it change anything you do.

#12 in the full Vault

These five are from a set of forty-two

The Sceptic’s Prompt Vault covers seven categories across the whole workflow, and sits inside The Sceptic’s Toolkit alongside the Playbook, the Trade Checklist, the Risk Cheat Sheet, the Journal, and the Position Size Calculator.

Set link

Educational content, not financial advice. Nothing here is a recommendation to buy or sell any instrument. Most retail traders lose money; only risk what you can afford to lose.
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