Thinking in Bets — A 12-Week Masterclass in Decisions Under Uncertainty With an AI Tutor - Make Better Calls With Incomplete Information.

A masterclass you actually finish. You already know the decision-making advice - trust your gut, follow the data, sleep on it - and none of it tells you what to do with a real choice under real uncertainty. This 12-week digital guide builds the actual mental model: separating good decisions from good outcomes, thinking in probabilities instead of false certainty, weighing options by what's likely and what's at stake, and updating your beliefs honestly when new evidence shows up. Each week you lead one fully scripted ~60-minute session - every step timed, every AI-tutor prompt copy/paste-ready - so no expertise or prep is required. An AI tutor works as your thinking partner - it never hands you the answer, it makes you name your confidence as a real number, imagine the plan failing before you commit, and grade the process instead of the result. Never used an AI chat assistant before? The guide's front matter walks you from zero to ready in about five minutes, free plan and all. Built for real calls at work, at home, with your health, and with people you care about - no gambling, no investing, no finance, just better thinking with the same incomplete information everyone has.

What you get

• A "Never used an AI chat assistant? Start here" onboarding that takes a complete beginner from zero to ready in about five minutes, using a free AI assistant - no paid plan needed.
• Four rescue prompts in the front matter for when a session goes sideways, you get a vague answer, you're stuck, or you just want to go deeper.
• An orientation that sets the one rule that changes everything: separate whether you decided well from whether it turned out well - they are different questions.
• 12 deep weekly sessions, each with a plain-language concept, a concrete worked example, a minute-by-minute ~60-minute session plan, copy/paste AI-tutor prompts at every step, a "show me" checkpoint, common mistakes to watch for, and practice.
• An AI-tutor prompt playbook — a probability-first Socratic starter, a rescue prompt for when a decision has you stuck, a "level me up" prompt that adds real-world mess, and a guardrail that keeps you from grading decisions by luck.
• A personal decision journal and checklist you build across the season and can run on any future decision.

The 12 weeks

1. Good Decisions vs. Good Outcomes
2. Thinking in Probabilities, Not Certainties
3. Expected Value in Everyday Terms
4. Updating Your Beliefs on New Evidence
5. Bias & Noise in Judgment
6. The Outside View
7. Pre-Mortems & Second-Order Effects
8. Deciding Well as a Group
9. Keeping Score: The Decision Journal
10. Project Week I: Plan a Real Decision
11. Project Week II: Decide, Act, and Set Up the Review
12. Demo Day & the Calibrated Mind

Who it's for

Adults who want to make better decisions when they can never know everything - anyone facing real calls at work, at home, with their health, or with people they care about. No math, statistics, or finance background assumed.

Why this instead of a free chatbot

A raw chatbot will happily tell you what to decide, or worse, tell you afterward that you were right all along. This pack ships the structure and discipline it lacks: a real 12-week progression from separating decisions from outcomes to working a real decision the whole way through, and a tutor set up to make you name an honest probability, imagine failure first, and tell good process apart from good luck before you ever act. You leave able to reason clearly under uncertainty - not just ask a bot what to do.

FAQ

• Do I need any experience? None. Week 1 starts with two decisions from your own life; every week builds one piece of the toolkit from there.
• Never used an AI chat assistant before? No problem. The guide opens with a "Start here" section that walks complete beginners through setup in about five minutes - a free AI assistant is all you need, no paid plan required.
• Which AI does it use? Works with any modern AI assistant - ChatGPT, Claude, Copilot, Gemini
• and free versions are enough. Every prompt is copy/paste-ready; no special software.
• Is this about gambling or investing? No. "Thinking in bets" is a mental model for reasoning under uncertainty, not a betting system. Every week uses everyday-life, work, health, and relationship decisions - there is no gambling, investing, or financial content anywhere in the pack.
• Will this make me overthink every little decision? No - the tools are for choices big enough to deserve ten focused minutes, not what to eat for lunch. You'll actually spend less time agonizing over the small stuff once the big stuff has a real process.
• Refunds? Standard marketplace refund policy applies.

Get the whole track

Sharpening more than your decisions? Get the whole adult toolbox — every adult-skills pack in one bundle.