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Analyse consequential choices with outside views, incentives, inversion, scenario arithmetic, opportunity costs, and explicit update conditions. Use for decision memos, premortems, strategy choices, or a requested red-team; not routine factual questions or a reason to overanalyse a small decision.

Use this Skill: https://skilld.dev/gh/tristanmanchester/agent-skills/wordly-wisdom

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referencesdecision-checklists.md

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Decision Checklists

Use these checklists selectively. Do not force every checklist onto every problem.

Universal high-stakes checklist

  • What is the decision?
  • What is the objective?
  • What is the time horizon?
  • What are the real options?
  • Which option is an obvious no-go?
  • What is the outside view?
  • Which 4 to 8 models matter most?
  • What incentives are in play?
  • What are the main failure modes?
  • What would change my mind?
  • What is the immediate next action?

Hire or partner checklist

  • Is this a trustworthy person?
  • Do incentives align over time?
  • Are we mistaking charisma for competence?
  • Can they answer the next hard question, or is this chauffeur knowledge?
  • What happens under stress, conflict, or disappointment?
  • What behaviour will this arrangement reward?
  • What is the downside if this goes badly?

Strategy or product checklist

  • What customer problem actually matters?
  • Is the moat real or merely presentational?
  • Does scale help us or mainly create complexity?
  • Where is the bottleneck?
  • What is the minimum winning move?
  • What will a smart rival do?
  • Which feedback loops will this create?
  • What happens if adoption is slower than hoped?

Investment or capital allocation checklist

  • What is the opportunity cost?
  • Is the downside survivable?
  • Is there a margin of safety?
  • Are the incentives trustworthy?
  • What are the hidden exposures?
  • Is this inside the circle of competence?
  • What are the second-order effects if the thesis is right?
  • What are the failure modes if the thesis is wrong?

Life decision checklist

  • Is this reversible?
  • Does it improve long-run optionality?
  • What misery is this likely to create if it goes wrong?
  • What am I rationalising because I want it to be true?
  • Which envy, fear, resentment, or identity pressures are active?
  • Who has made this mistake before?
  • What would an older, calmer version of me think?

Premortem workflow

  1. Assume the decision failed.
  2. Write the failure headline.
  3. List 5 to 10 reasons it failed.
  4. Mark which reasons are controllable.
  5. Add guardrails for the top controllable reasons.
  6. Re-evaluate whether the upside still justifies the risk.

Postmortem workflow

  1. What happened?
  2. What did we expect?
  3. Which assumptions were wrong?
  4. Which misjudgment tendencies were active?
  5. Which incentive was mis-set?
  6. What was controllable?
  7. What was luck?
  8. What process change should we keep next time?

Source: SKILL.md on GitHub

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2 warnings1mo5 checks · Risk MEDIUM
  • Gen Agent Trust Hub1mo

    The skill provides a framework for decision analysis using mental models and local Python scripts. It is flagged as medium risk due to metadata poisoning, as it claims to be authored by 'openai' while originating from an unrelated developer 'tristanmanchester'. Additionally, the skill's ingestion of untrusted user data for decision memos and script processing creates a surface for indirect prompt injection and potential arbitrary file writes.

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    Risk: LOW · No issues

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  • ZeroLeaks6mo

    Score: 93/100 · 2 sections analyzed

Signed by skilld at 3323bc9. This ties the file your Agent reads to that commit on GitHub. It does not review the instructions.

Last checked against GitHub 2 weeks ago.

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Other metadata
compatibility
Core reasoning needs no special tools. Optional arithmetic helpers require Python 3.10+ and use only the standard library. Time-sensitive or specialised claims require current relevant sources.
metadata
{
  "version": "4.0.0",
  "reviewed": "2026-09-13",
  "source-book": "Poor Charlie's Almanack"
}

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