The Stoic Pre-Mortem: A 20-Minute Exercise That Makes Every Business Decision More Intelligent
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The Stoic Pre-Mortem: A 20-Minute Exercise That Makes Every Business Decision More Intelligent
Most Business Plans Are Built on Optimistic Bias
You sit down to plan the launch. The numbers are clean. The timeline looks reasonable. The copy resonates when you read it. The strategy makes sense because you constructed it from the best-case scenario—and your brain filled in all the details that would need to go right.
What you did not construct is the failure scenario. Not the catastrophic failure, which is too extreme to be useful. But the realistic failure—the one where one or two critical assumptions turned out to be false, or where one variable moved against you. That's the scenario missing from your plan.
The Stoics understood this 1,800 years before modern cognitive science quantified it. They built plans from the opposite direction. Imagine the worst. Prepare. Then act without fear.
Two Frameworks, One Concept: The Cognitive Lineage of Pre-Mortem Analysis
In 1998, cognitive scientist Gary Klein conducted research on how teams make decisions. He discovered a technique that surfaces hidden risks that forward-planning systematically misses: the pre-mortem.
Klein's framework is precise: imagine it's 12 months from now and your project has failed completely. Your job is to explain, in specific detail, what went wrong. This cognitive move is different from brainstorming risks. You are not asking "what could go wrong." You are stating, with certainty: "This has failed. Explain why."
The Stoic philosophers, operating in a very different context, arrived at an identical cognitive move. Marcus Aurelius called it premeditatio malorum—the premeditation of adversity. Visualize failure. Understand it. Then act with the knowledge that you have prepared yourself for this outcome.
Klein gave us the modern cognitive protocol, validated by research. The Stoics gave us the philosophical foundation and the permission to think about failure without being labeled pessimistic. You need both. The protocol is empty without the philosophy. The philosophy is abstract without the protocol.
Why Standard Risk Management Fails to Surface Real Failure Modes
Spreadsheet risk matrices are too abstract. You score a risk from 1-10 for probability and impact. The numbers are defensible. The risks are real. But the exercise generates no emotional pressure and no specific narrative. You cannot prepare for a vector on a matrix.
Scenario planning usually operates at the macro level. You plan for interest rate changes, competitive threats, market trends. These are valuable. But they do not map onto the specific failure modes of your specific project, with your specific team and your specific market position.
Casual "what could go wrong" brainstorming is too brief. You spend 10 minutes in a meeting throwing out risks. The group lands on the top 5. You feel like you have thought about failure. You have not. You have generated a list of fears, not a narrative of how you got there.
The Stoic pre-mortem is different. It demands a failure narrative. It demands specificity. It demands that you sit with the failure long enough to reverse-engineer how it happened. That cognitive work—the 18-minute commitment to sitting with a specific failure scenario—is what separates this from standard risk management.
The Stoic Pre-Mortem Protocol: Complete Step-by-Step
This is the centerpiece. The protocol is the boundary between philosophy and action. Run this the same way every time. Do not optimize it. Do not skip steps. The discomfort and the structure are the point.
SETUP (2 minutes)
Use physical paper only. No laptop. No phone in the room.
State the decision or project in one clean sentence at the top of the page.
Example: "Launch a 40% price increase on the coaching offer."
Set a timer for 18 minutes. You will use all of it.
STEP 1 — The Failure Declaration (3 minutes)
Write at the top of a fresh section: "It is [DATE + 12 months from now]. This project/decision has failed completely. The outcome is significantly worse than expected."
Now write: what does "completely failed" actually look like? Be specific. Not "revenue was down." Write: "Revenue dropped 28%, we lost 7 clients in month 3, and we had to drop the price back to the original by month 8." Write the failure in numbers, outcomes, and consequences. Write what it cost. Write what it meant for the team.
This is not speculation. This is declaration. Commit to this version of failure.
STEP 2 — Reverse Engineering (7 minutes)
Ask yourself: "How did we get here? What was the first thing that went wrong?"
Write the failure narrative in reverse chronological order—from the catastrophic outcome backwards to the decision point. Do not write a timeline. Write causality. "We lost 7 clients because they said they did not see the value at the higher price. We did not see it coming because we assumed client lifetime value was stable. We did not test our assumption because we were confident based on past growth."
Focus on three questions as you reverse-engineer:
- What assumption did we make that turned out to be wrong?
- What did we ignore because it was uncomfortable?
- Where did we have the option to catch this and chose not to?
Write these answers. This is the real work.
STEP 3 — The Premeditatio Check (5 minutes)
Reread what you wrote. For each failure mode identified, ask three questions:
- Is this preventable with current information? Could you act now to prevent this?
- If yes: what specific action prevents it and when does it happen? Write the protocol. "We conduct a client survey in week 1 to measure price sensitivity before full rollout."
- If no (genuinely outside your control): how do you respond if it happens? Write the response protocol. "If we lose 5+ clients by month 2, we revert to the original price and run the offer at 80% price increase instead."
This is not planning. This is response preparation. You are telling your future self: "If this happens, do this."
STEP 4 — Decision Confirmation or Adjustment (3 minutes)
After the exercise: do you still make the same decision? Yes or no.
If yes: proceed with the response protocols in place. You are not more confident. You are better prepared. You have seen the failure. You have planned the response. You can act.
If no: what specifically changed? This is valuable information. The pre-mortem has done its job. You have saved yourself from a decision that your deeper mind knew was risky.
Applied Example: Running the Stoic Pre-Mortem on a Real Decision
Here is what the protocol looks like in practice. The scenario: you are deciding whether to raise prices by 40% on your coaching offer. You have 200 active members. You have been flat on growth for 2 months. The raise would give you breathing room and force quality over quantity.
Scenario: 40% Price Increase on Coaching Offer
Revenue from the offer is down 34%. We now have 87 active members (dropped from 200). We did attempt the price increase, but by month 3 we reverted it. We spent 6 months trying to add new members at the higher price and it did not work. We lost a month of velocity trying to recover by offering discounts, which damaged our positioning. A competitor launched a lower-priced option in month 4 and captured the members we lost.
Why did we lose 113 members? First: the price sensitivity was higher than we estimated. We assumed 20% churn. We got 45% in month 1. We did not see it coming because we based our assumption on past churn at lower price points—but we did not account for member acquisition change. We used to have referral growth. We now have marketing-driven growth. Different member quality. We ignored this data because it contradicted our decision.
Second: we did not have a back-end strategy. We raised price with zero new offer upgrade or differentiation. We told people we were now more expensive. We did not tell them why they should stay. We had the data to do this (member feedback from surveys). We chose not to review it in month 2 because we were focused on the launch.
Third: we did not build a kill switch. By the time we decided to revert the price, we had already damaged the narrative ("we are not serious about our value" or "this was a test"). The revert looked like failure, not adjustment.
Preventable (before launch): We conduct a member survey in week 1 asking about price ceiling for the offer. We also segment members by acquisition source (referral vs. marketing) and model churn separately. We spend 2 days on this before launch. Cost: minimal. Information gain: high.
Preventable (if we have early signal): We commit to measuring churn in week 1 and week 2 only. If churn exceeds 30% in either week, we run a member retention call (not a retention discount) to understand the decision. We do this before making any public adjustments. Timing: weeks 1-2 only.
Uncontrollable (but can prepare for): If we lose 50+ members despite retention calls, we execute the price revert. But we do it with a clear narrative: "We are running an 8-week optimization. Price is temporarily reduced to $X while we rebuild the offer." This is not failure. This is testing. We signal stability and deliberation.
After writing this: do we still raise the price 40%? Revised decision: yes, but we do the member survey and segmentation first. If survey data shows price ceiling is lower than our 40% increase, we raise 20% instead. We run week 1-2 churn measurement. If churn is above 35%, we execute the retention call protocol. We have a kill switch if needed, but we signal it as optimization, not reversal.
The original decision was identical. The execution plan is completely different.
Common Mistakes When Running Pre-Mortems
- Too optimistic in the failure narrative. You write "things did not go as planned" instead of specific numbers and consequences. The exercise requires you to commit to the failure. Vague failure scenarios teach you nothing.
- Skipping the response protocol. You identify risks but do not write protocols. Prevention is not the only job. Preparation for uncontrollable failure modes matters equally. Do not skip step 3.
- Group dynamics destroy honesty. If you run this in a team setting, do not workshop it. Each person writes independently first. Then you share and discuss. Shared discussion kills the individual honesty the exercise requires.
- Running it too quickly. 18 minutes is the minimum. The discomfort of sitting with failure is part of the cognitive work. Rushing to finish cheats the protocol.
- Treating it as a one-time exercise. The pre-mortem is not a decision checkpoint. It is a compound protocol. Monthly pre-mortems build pattern recognition in your failure-prediction system. The 12th pre-mortem is orders of magnitude more useful than the first.
The Compound: Building Pattern Recognition Through Repeated Pre-Mortems
One pre-mortem on one decision is useful. Twelve pre-mortems over 12 months is a discipline that restructures how you think about decisions.
After your third monthly pre-mortem, you will notice: you are faster at reverse-engineering. You see failure patterns you missed before. The assumptions you keep identifying as problematic become clearer. You start spotting the same failure modes appearing in different decisions.
After six months, the protocol is no longer a deliberate exercise. You start reverse-engineering failure scenarios before you consciously decide to. Your brain has learned the pattern. You default to thinking backwards from failure.
After 12 months, you have built a personal diagnostic system. You can run a pre-mortem in 12 minutes instead of 18. You know your blind spots. You know which assumptions you keep getting wrong. You know the failure modes that matter for decisions in your specific market and business model.
This is the compound of discipline. Not motivation. Discipline. You run the protocol whether you feel like it or not. You use the same setup, the same timing, the same structure. The consistency is what builds the skill.
How to Build Pre-Mortems Into Your Decision Practice
Do not run a pre-mortem on every decision. This is a protocol for decisions above a specific threshold: decisions that commit 3+ weeks of your time, decisions that require capital allocation above $5,000, decisions that affect more than 2 people on your team, or decisions you feel conflicted about.
Set up a monthly pre-mortem schedule. First Tuesday of the month, 9am, 30 minutes blocked. The pre-mortem itself is 18 minutes. The other 12 minutes are for you to read your pre-mortems from the past 3 months and identify patterns.
Use a physical decision journal. Dated entries. One decision per page. At the bottom, write the date you will revisit this decision (usually 6-12 weeks out, when you have real data on whether the failure scenarios materialized). Review the actual outcome against your pre-mortem. This feedback loop is crucial.
Do not store these documents digitally or share them widely. This is a private tool. Privacy allows honesty. You can write the failure scenario without worrying about how it looks to your team or your business partner. The pre-mortem is not a presentation. It is preparation.
Frequently Asked Questions
Build Your Decision Intelligence
The pre-mortem is day 3 of the 5-Day Stoic Operator Challenge. Learn how Stoic philosophy maps onto modern decision science. Build the protocols that compound into clarity.
Start the ChallengeRelated Reading
For a deeper exploration of how premeditatio malorum applies to business decisions, see our guide to Premeditatio Malorum for the Entrepreneur Decision-Maker.
For the complete framework on how Stoic discipline compounds into operational excellence, explore the 5-Day Stoic Operator Challenge.