Probability Thinking Decision Assistant
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About this skill
Problem
Important decisions often get distorted by emotion and single outcomes: job changes, investments, startups, and partnerships can feel like “I should be able to make it work,” while ignoring base rates, payoff, worst-case loss, and repeatability. The Probability Thinking Decision Assistant turns these choices into structured variables instead of relying on gut feel.
How it works
The skill evaluates options across six dimensions: win rate, payoff, base size, risk, information, and fault tolerance. A typical workflow includes:
- listing options A/B/C and defining their upside and downside;
- replacing intuition with historical examples, market data, or comparable outcomes;
- estimating expected value and checking whether the worst case is survivable;
- updating the prior probability as new information arrives, while keeping a Plan B and stop-loss.
It also frames decision-making in four levels: intuition, basic probability, expected value, and systematic probability, helping identify where current reasoning sits.
Boundaries
This is useful for career moves, transitions, investments, project planning, and trust judgments that benefit from repeated evaluation. It provides a structured assessment and risk framing, not professional legal, financial, or medical advice; when data are weak, probability estimates remain assumptions that should be validated with more information and small experiments.
Use Cases
- Compare stable big-tech employment versus startup equity upside before a job move, weighing win rate, payoff, and reversibility.
- Estimate rise probability and upside/downside ratio before buying a stock, then check expected value and position sizing.
- Evaluate industry success rate, failure loss, and living-cost buffer before deciding whether to quit for a startup.
- Assess a partner or vendor's delivery record and breach cost before deciding how much trust to place in the relationship.
Best For
- Career switchers evaluating path success rate, growth payoff, and trial-and-error cost.
- Retail investors deciding position size based on odds, stop-loss room, and long-run expected value.
- Founders and operators designing multi-path experiments and risk controls to limit single-point failure.
- Business owners judging partner trust, breach cost, and payoff before committing resources.
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