Coaching practices for I Size Up a New Idea Against Some Image in My Head of What Its Kind Looks Like and Spit Out a Verdict Without Ever Naming the Comparison I'm Running or Asking Whether It's Even the Right Thing to Measure Against

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Does this sound like the set of challenges you might be facing?

  • I size up a new idea against some image in my head of what its kind looks like and spit out a verdict
  • A half-formed idea or odd little fragment shows up and I kill it on the spot
  • I grab the first idea that pops up and start poking holes in it immediately, so I never get more than two or three options on the table
  • The second an idea pops up I’ve already told myself why it won’t work, so it dies before I’ve even finished thinking it
  • Every approach I come up with sounds like me, because I keep ruling out anything that doesn’t feel like something I’d do

Practices that may help

  1. Name the prototype you’re comparing against before deciding
    Make the prototype you’re using as a reference explicit — hidden templates bias decisions without scrutiny.
    The Representativeness Heuristic — Judging by Resemblance
  2. Collect everything that resonates — without editing
    Build a practice of gathering ideas, images, sounds, and fragments without evaluating whether they are "good enough."
    The Creative Act: Rick Rubin’s Approach to Making
  3. Ideate — generate options before judging
    Produce many candidate solutions, deferring evaluation until you have quantity.
    Design Thinking, Step by Step
  4. Defer judgment during generation
    Generate ideas with no criticism, then evaluate in a separate pass.
    Divergent Thinking: Generating Many Ideas
  5. Ask what a specific other person would do
    Step into a named other’s perspective to access approaches you would not generate as yourself.
    Oblique Strategies, Made Practical
  6. Use multiple analogies for the same problem
    Draw on at least two different analogies for a new problem and see where they agree and diverge.
    Analogical Reasoning
  7. Prototype to think, not to finish
    Build or sketch something rough specifically to learn what you actually want.
    Quantity Over Quality: How More Drafts Produce Better Work
  8. Defer all judgment during ideation
    Separate the generating phase from the evaluating phase — they cannot run simultaneously without killing output.
    Creative Confidence, Made Practical
  9. Defer judgment during ideation
    Separate generating ideas from evaluating them — criticism comes later, never during.
    Osborn’s Brainstorming Rules, Made Practical
  10. Interrogate whether similarity is doing the work
    When assessing probability or quality, ask whether you’re really judging similarity to a prototype.
    Attribute Substitution: When Your Brain Answers a Different Question

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