Coaching practices for Planning for Being Wrong
Describe almost anything you are working through and IX Coach finds the practices whose real-world fit is closest. For Planning for Being Wrong, these are the strongest matches in the current practice library.
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 always tell myself it’ll take this long or cost this much, and somehow it always runs over and I’m scrambling
- My whole plan only works if everything goes roughly as expected, and I lie awake aware that one bad surprise
- 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.
- When I ask myself "what could go wrong with this plan," I either draw a blank or come up with one vague worry
Practices that may help
- 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 - 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 - Build room for error (margin of safety)
Plan so that being wrong is survivable, not catastrophic.
The Psychology of Money, Made Practical - 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 - The Planning Fallacy — Why Your Estimates Are Always Wrong
The planning fallacy is the well-replicated tendency to underestimate completion times even when you know your past projects ran late. The fix is not to "try harder" — it is to switch from imagining the ideal future scenario to consulting your own base-rate history and similar projects. - Run the basic pre-mortem
Assume the plan failed, then have everyone write down why.
The Pre-Mortem: Imagine It Already Failed - Log actual vs. estimated time for every task
Build a personal database of your own estimation errors so you can calibrate future predictions.
The Planning Fallacy — Why Your Estimates Are Always Wrong - 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 - Reference class forecasting
Before estimating, look up how long similar past projects actually took — not how they felt.
The Planning Fallacy — Why Your Estimates Are Always Wrong - Pre-commit to resolution criteria before making a prediction
Define exactly what counts as "I was right" before the outcome happens.
Calibration Training
Related concerns
- Planning Assumptions Audit
Every plan rests on assumptions — list them and ask how likely each one is.
Name the assumptions that must hold for the plan to work
- When Margin Of Safety Estimate Conservatively
When uncertain, use a pessimistic estimate as your working assumption — not your best guess.
Estimate conservatively and act on the conservative number
- Adaptive Planning Uncertainty
Anticipate the specific obstacles most likely to block your plan and pre-decide your response to each.
Plan for obstacles with coping plans
- How To Avoid Planning Fallacy
The planning fallacy is the well-replicated tendency to underestimate completion times even when you know your past projects ran late. The fix is not to "try harder" — it is to switch from imagining the ideal future scenario to consulting your own base-rate history and similar projects.
- Pessimistic Planning
When uncertain, use a pessimistic estimate as your working assumption — not your best guess.
- Planning Assumptions
Every plan rests on assumptions — list them and ask how likely each one is.
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