Coaching practices for I'm About to Commit to This Plan and on Paper it Looks Solid but a Quiet Part of Me Suspects I'm Too Sold on it to See the Holes I Want to Assume It's Already Gone Wrong and Find Out Why Before I'm in Too Deep to Change Course

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Does this sound like the set of challenges you might be facing?

  • I’m about to commit to this plan and on paper it looks solid, but a quiet part of me suspects I’m too sold on it to see the holes
  • I’m about to commit real time and money to this plan, and it looks solid
  • I’m about to commit to this plan and I can feel how badly I want it to work
  • I’m about to commit to this timeline and on paper it all looks fine, but I have a nagging feeling I’m glossing over the ways it could go sideways because admitting them now feels like talking myself out of it before I’ve even started.
  • My plan feels solid until I notice it quietly depends on a whole stack of things just going my way

Practices that may help

  1. The premortem (imagine the project already failed)
    Before starting, assume the plan has already failed and ask why — then fix it now.
    Premeditatio Malorum, in Depth
  2. Run a pre-mortem before committing to a plan
    Imagine the plan has already failed and ask what went wrong.
    Confirmation Bias: Seeing What You Expect to See
  3. Steelman objections to your own plans
    Before committing to a plan, state the strongest case against it in its most compelling form.
    Steelmanning
  4. Run a premortem before committing
    Imagine the project has already failed and work backwards to find why.
    The Planning Fallacy — Why Your Estimates Are Always Wrong
  5. Name the assumptions that must hold for the plan to work
    Every plan rests on assumptions — list them and ask how likely each one is.
    Margin of Safety
  6. Run a premortem before committing
    Imagine the decision has already failed — then ask why.
    Thinking in Bets
  7. Run a pre-mortem to interrupt forward narrative construction
    Before committing to a plan, imagine it failed completely — then generate the most plausible story of why.
    The Narrative Fallacy: Why We Can’t Stop Making Stories
  8. Pre-mortem your personal goals
    Apply the technique solo to a habit, project, or life decision.
    The Pre-Mortem: Imagine It Already Failed
  9. Invoke the outside view before committing to any significant plan
    Before finalizing a plan or forecast, ask "How did similar things go?" as the first checkpoint.
    The Outside View
  10. Turn top risks into tripwires
    Set a specific signal that tells you a feared failure is starting to happen.
    The Pre-Mortem: Imagine It Already Failed

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