Sharper Thinking

Problem Solving · October 13, 2026

Working Backward From the Failure You're Trying to Avoid

Imagining the plan has already failed — before you've started — surfaces risks that optimism quietly talks you out of seeing.

Imagine the Failure First

Most planning starts by imagining success and working forward. A premortem does the opposite: imagine the project has already failed, then work backward to explain why. It's a small shift that gives permission to voice doubts optimism usually suppresses.

Run the Exercise Before You Commit

  • Picture it's six months later and the plan has clearly failed.
  • Write down every plausible reason why, without softening any of them.
  • Pick the two most likely causes and fix those before you start.

Pessimism, Used on Purpose

Inventors who build things that last aren't the most optimistic people in the room — they're the ones willing to imagine failure early enough to prevent it.

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