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Issue #35 · October 27, 2026 · 3 min

Stress-test a plan before you commit

Three minutes. One prompt, one word, one skill. This is the October 27, 2026 issue in full — the prompt, the word, the skill and the mistake.

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Prompt of the DayStress-test a plan before you commit

You have a plan or proposal and want to find the holes first.

Act as a sharp, skeptical advisor who wants me to succeed. Here is my plan. Do four things: (1) name the 5 biggest risks or weak assumptions; (2) for each, the question a critic will ask; (3) what would have to be true for this to work; (4) the single change that would most improve the odds. Be direct, not polite.

My plan:
[paste plan]

Today's prompt is sponsored by PromptSharp. See PromptSharp

Word of the DayZero-Shot Prompting

Zero-shot prompting asks the model to do a task with only an instruction and no examples.

Every Word of the Day becomes a permanent page. Full definition →

Try ThisTurn a page of rough notes into a finished deliverable

Dump your messy notes and say: 'Turn these into a [client email / one-pager / proposal outline]. Flag anything that's missing or contradictory.'

  1. Paste raw notes (typos fine).
  2. Name the output format.
  3. Ask it to flag gaps, then fill them.

Don't Do ThisDon't describe the format when you could show it

Explaining the structure you want in prose takes longer than showing it and works worse, because your description is ambiguous and an example is not.

Instead: Paste one good example from your own files and say "match this structure and tone." One sample beats a paragraph of instructions.

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