/prepare

Prepare to Be Wrong

Counter overconfidence by planning for both success and failure. Set tripwires and fallbacks before you need them.

Instructions

Assume you might be wrong. Plan for how you'll detect problems and what you'll do. This isn't pessimism—it's preparedness.

Output Format

**Decision/Plan**: [What you've decided to do]

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Premortem

*Imagine this decision failed completely. What happened?*

**It's 6 months later. This was a disaster. Looking back, what went wrong?**

| Failure Mode | Likelihood | Severity | Was It Predictable? | |--------------|------------|----------|---------------------| | [what failed] | High/Med/Low | High/Med/Low | [Yes/No] | | [what failed] | High/Med/Low | High/Med/Low | [Yes/No] | | [what failed] | High/Med/Low | High/Med/Low | [Yes/No] |

**Which failures can we prevent now?**

| Failure | Prevention | |---------|-----------| | [failure] | [how to prevent it] | | [failure] | [how to prevent it] |

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Bookend the Future

**Best realistic case:** > If everything goes well, what does success look like? [Description]

**Worst realistic case:** > If things go badly, what does failure look like? [Description]

**Are we prepared for the worst case?** [Yes/No/Partially]

**What would make the worst case more survivable?**

• [Mitigation 1]
• [Mitigation 2]

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Set Tripwires

*Decide in advance what would cause you to reconsider*

| Tripwire | Trigger Condition | Action If Triggered | |----------|-------------------|---------------------| | Date | [specific date to review] | [reassess decision] | | Metric | [if X drops below Y] | [specific action] | | Event | [if specific thing happens] | [specific action] | | Resource | [if we spend more than X] | [stop and evaluate] |

**Tripwire reminder set?** [Where/how will you be reminded?]

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Safety Net

**If we're wrong, what's our fallback?**

| If This Happens | Our Response | |-----------------|--------------| | [scenario 1] | [fallback plan] | | [scenario 2] | [fallback plan] |

**Reversibility Assessment**

| Aspect of Decision | Reversible? | Cost to Reverse | |-------------------|-------------|-----------------| | [aspect] | Yes/No/Partially | [cost] |

**Is there a way to make this decision more reversible?** [Possibility]

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Confidence Calibration

**How confident are you this will work?** [___]%

**Base rate: In situations like this, what's the typical success rate?** [___]%

**Is your confidence higher than the base rate? Why?** [Justification or recalibration]

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Commitment Plan

**We're committing to this decision, while also:**

1. **Watching for**: [early warning signs] 2. **Revisiting on**: [specific date] 3. **Stopping if**: [tripwire condition] 4. **Pivoting to**: [fallback option] if needed

**Decision with safeguards:** > [State the decision along with key safeguards]

Guidelines

• Confidence feels good but isn't correlated with accuracy
• "We'll figure it out" isn't a plan—specify the fallback
• Tripwires work because they're set before emotions cloud judgment
• Reversible decisions need less preparation than irreversible ones
• The goal isn't to be pessimistic—it's to be prepared

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