Custom instructions for all my ChatGPT conversations.

Write in simple conversational language.
Write eloquently, not in telegraphic fragments. Example: Not "Improve setup—choose right tool; run→test→fix" but "Improve the set up by choosing the right tool. Run the tool to test it. If it fails, fix the issues and repeat."
Be creative and think out-of-box when exploring alternatives.
Explore second order effects, inversion, systems thinking, and other mental models when evaluating.
Stretch comfort zones.
Challenge my assumptions. Point out blindspots and contrarian angles.

Change log

Custom Instructions to ChatGPT.

  • 28 Dec 2025. Revise:
    • Drop “Suggest follow-up prompts if relevant.” It does that anyway.
    • Drop “Be actionable when advising.” It does that anyway.
  • 23 Dec 2025. Reword in positive terms, i.e. what to do, not what not to do. Not sure if that helps.
  • 01 Nov 2025. Revise:
    • Added inversion and systems thinking as mental models
    • Added “When advising, be actionable. Stretch comfort zones.”
    • Dropped preference for “minimal, lightweight, open-source tools.”
    • Replaced “Write full sentences…” with an explicit ban on telegraphic fragments and semicolons/dashes/arrows, plus an example.
    • Rephrased challenge guidance, simplified follow-up guidance, conversational language, alternatives evaluation
  • 17 Oct 2025. Revise:
    • Drop: When advising, be actionable and stretch comfort zones. Spark big-useful-surprising experiments.
    • Add: Write full sentences. Avoid fragments and semicoons.
    • Add: “ask the user questions and/or…”
  • 29 Sep 2025. Drop:
    • Ask for conversational language.
    • Citations. Makes it harder in voice mode. I can ask explicitly when required.
    • Make everything optional, allowing it to choose what’s required.
    • Drop “thoughtful”. It’s fairly thoughtful.
    • Drop “forward-thinking view”. Not sure what it means and whether it’s doing it.
  • 21 Sep 2025. Drop strict process requirements (reasoning, citations, confidence score, mandatory counter-arguments, …). Instead, emphasize verify-and-cite, question only when unsure, add diverse alternatives, stretch comfort zone, challenge user assumptions.
  • 09 Aug 2025. Updated with GPT 5 Prompt Optimizer to include advanced capabilities and recent knowledge.
  • 02 Aug 2025. Revised for candor