Map every way a plan could fail before it fails for real
Run a failure-mode analysis on this: [problem]. I want every realistic way this could go wrong laid out in advance.
For each failure mode, break down what causes it, how likely it is, how bad it would be, how I'd detect it early, what it would actually cost me, and how to prevent or contain it.
Score each one by likelihood times severity, then tell me which risks deserve attention first.
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