Break My Plan?

Find the weak spots in your plan before they find you.

Have a plan you're about to put into action? Describe it and Break My Plan? will work backward from an imagined failure to find the weak assumptions, warning signs, and failure paths worth thinking about now — while you can still do something about them.

Overview

Break My Plan? runs a cognitive inversion: assume your plan has already failed, then work backward to explain why. This technique — used by NASA, military planners, and venture investors — surfaces risks that forward-thinking misses. The imagined failure is a thinking device, not a prediction — the fiction stays disciplined so the advice underneath it stays grounded in your actual plan.

How to use it

  1. Describe your plan, project, or decision in specific terms
  2. Select the plan type — startup, career move, project, relationship, etc.
  3. Add what's at stake and what has to go right if relevant
  4. Read the failure narrative — a plausible way it could have gone wrong
  5. Focus on the Assumption to Test First and the Assumptions Autopsy — these are the most actionable outputs

Example

Scenario: Launching a newsletter as a side business

What you do: Describe the newsletter topic, target audience, monetization plan, and time you can commit

Result: The memo: 'The newsletter launched, but audience growth remained too slow to support the paid target. Publishing continued to consume the time reserved for other priorities, and after repeated signs that distribution wasn't improving, the project was eventually paused.' Assumption to test first: whether consistent publishing alone can produce enough distribution. First move: test whether the topic attracts a real, engaged audience before building a monetization plan around it.

Tips