Plan a self-sabotage

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Plan a self-sabotage
Author: Stijn Dejongh
Published on: 2023-09-19 00:00:00 +0000 UTC
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Problem Statement

You have an idea and want to strengthen it against negative forces.


  • Discover critical risks to your ideas.
  • Reflect on ways to cope with setbacks.
  • Harden your idea by limiting failure conditions.

Contextual forces

What is this? These describe factors at play that influence the outcome of the practice. They are not necessarily good or bad, but they are important to be aware of. Some contextual forces are enablers, giving the practice a higher chance of being useful. Others are deterrents, making the practice less useful in your given context.


  • You are able to think of creative ways to sabotage an idea.
  • You are willing to attack your own creation, in order to strengthen it.
  • You have access to resources or prior knowledge about common misfortunes that happen in your context.
  • You have access to others with knowledge of your context, that you can ask for feedback or learn from their experiences.


  • You do not have access to others / prior knowledge.
  • You have difficulties finding/accepting issues with your own ideas or creations.


  • Challenge your own ideas
    • Begin by actively sabotaging your own ideas and plans.
    • Delve deep into your suggested approach and ask, “How can I ensure this fails?”.
    • Encourage creativity and explore beyond common expected issues.
    • The effectiveness of this technique relies on your willingness to undermine yourself.
  • Create a Comprehensive List
    • Compile a list of all the ways you can guarantee failure.
    • Organize these potential failure scenarios from “most impactful” to “least impactful.”
    • Prioritize addressing the five most impactful scenarios as a starting point.
  • Assess Likelihood (Optional):
    • For a more thorough evaluation, assign a likelihood rating to each “sabotage” scenario, ranging from high probability to low probability.
    • This assessment will allow you to create a 2-by-2 matrix, helping you visualize and prioritize potential issues.
  • Mitigate Impact of Failures:
    • Consider and develop strategies to mitigate the three most likely high-impact failure scenarios.
    • Consider and develop strategies to mitigate the three least likely high-impact failure scenarios.1
  • Track potential risks:
    • During execution of your plan, actively track and reassess the risks to your idea. Be prepared to act!
    • Concentrate your attention and efforts on the failure modes that have the highest impact, as identified in the matrix.
A 2-by-2 matrix showing risks to an idea/plan ordered by impact and likelihood

By following this systematic approach, you can proactively strengthen your ideas against negative forces, ensuring they are more resilient and better prepared for potential challenges.


Creativity and Blind Spots

  • Creative thinking can make it challenging to identify flaws in your plans.
  • Common cognitive biases come into play:
    • Selection bias: Only taking into account part of the information available to you, as it fits what you want to believe.
    • Effort justification: Overvaluing something, because you have put effort into it.
    • Illusion of validity: Overestimating your ability to interpret and accurately predict the outcome of when analysing a set of data.
    • Illusion of explanatory depth: Believing you understand something much more thoroughly than you actually do.

Perspective Shifting

  • Emotionally investing in your ideas can hinder clear reasoning.
  • Shifting from “constructive mode” to “destructive mode” mentally helps distance yourself from biases.


  1. The idea being that the unlikely, high-impact failure modes are usually what catches people by surprise, and tend to ruin a plan as no one bothered to think about mitigation strategies. An example from the technology world: “What if a hurricane destroys our data centre?”. ↩︎