Coaching practices for When I Ask Myself What Could Go Wrong with This Plan I Either Draw a Blank or Come Up with One Vague Worry It's Like My Own Optimism Keeps a Lid on the Real Risks and I Can't Seem to Look at Them Squarely Until It's Too Late
Describe almost anything you are working through and IX Coach finds the practices whose real-world fit is closest. For When I Ask Myself What Could Go Wrong with This Plan I Either Draw a Blank or Come Up with One Vague Worry It's Like My Own Optimism Keeps a Lid on the Real Risks and I Can't Seem to Look at Them Squarely Until It's Too Late, these are the strongest matches in the current practice library.
Does this sound like the set of challenges you might be facing?
- When I ask myself "what could go wrong with this plan," I either draw a blank or come up with one vague worry
- 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 excited about this plan and so committed to it that I can’t honestly see what might sink it
- I’m about to commit real time and money to this plan, and it looks solid
- 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.
Practices that may help
- Run the basic pre-mortem
Assume the plan failed, then have everyone write down why.
The Pre-Mortem: Imagine It Already Failed - 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 - Run a premortem before committing
Imagine the decision has already failed — then ask why.
Thinking in Bets - 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 - 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 - 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 - Run a pre-mortem from the outside-view perspective
Imagine the project has failed — then ask which base-rate failure type caused it.
The Outside View - Estimate conservatively and act on the conservative number
When uncertain, use a pessimistic estimate as your working assumption — not your best guess.
Margin of Safety - Rate each failure by likelihood and impact
Turn the raw failure list into a prioritized set of risks to mitigate.
The Pre-Mortem: Imagine It Already Failed - 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
Related concerns
- When Thinking In Bets Run A Premortem
Imagine the decision has already failed — then ask why.
Run a premortem before committing
- Find Flaws In Your Plan
Before starting, assume the plan has already failed and ask why — then fix it now.
The premortem (imagine the project already failed)
- How To Plan For Failure
Assume the plan failed, then have everyone write down why.
Run the basic pre-mortem
- Imagine Failure Before Starting
Balance failure analysis with an equally concrete picture of what success requires.
Pair the pre-mortem with a clear success vision
- When Confirmation Bias Pre Mortem For Plans
Imagine the plan has already failed and ask what went wrong.
Run a pre-mortem before committing to a plan
- When Outside View Pre Mortem Outside View
Imagine the project has failed — then ask which base-rate failure type caused it.
Run a pre-mortem from the outside-view perspective
Describe your situation in your own words to search the complete practice library.