The Iteration Trap: When AI Makes You a Spectator

Key Facts

  • The trap: iterate with AI → stop reading output → run more cycles → hope for magic
  • Root cause: you don’t have clear acceptance criteria - you’re iterating because you don’t know what you want
  • The iteration trap is really a clarity trap
  • “Read after every cycle” treats the symptom, not the cause
  • The real failure: “I couldn’t articulate what was wrong with it”

The Story

  • Ran playbook generation with two LLMs connected
  • Kept iterating, expecting something great to emerge
  • Stopped actually reading what was being produced
  • Just wanted to run one more cycle, wait for the magic
  • Finally read the output: “I don’t think it’s really good… just presenting the data”
  • The iteration felt productive. The output wasn’t.

The Pattern

idea
  → iterate with AI
    → stop reading
      → run more cycles
        → hope for magic
          → finally read output
            → meh

You became a spectator hoping the slot machine pays out. The AI was generating, you were waiting, nobody was thinking.

Why This Happens

  • You don’t have clear acceptance criteria - without knowing what “good” looks like, you can’t evaluate
  • Iteration feels like progress - dopamine hit of activity without cognitive load of evaluation
  • Evaluation is harder than generation - requires you to have a mental model of what you want
  • Variable reward schedule - unpredictable output quality creates slot machine dynamics

The Real Fix

“Read after every cycle” treats the symptom, not the cause. You can read and still be trapped - nodding along, prompting again because “it’s not quite right” without knowing why.

Structural fixes that actually work:

  1. Define done before you start - Write 2-3 specific criteria for what “good” looks like. Not vibes - concrete checkboxes.

  2. Constrain cycles upfront - “I will do 3 iterations max.” Forces you to evaluate seriously because you’re spending a finite budget.

  3. Externalize the evaluation - After each output, write: “This is/isn’t acceptable because ___.” If you can’t fill in the blank, you don’t have criteria. Stop iterating and go define them.

  4. Default to single-shot - Treat iteration as expensive. If you need 5+ cycles, the problem is upstream (unclear requirements, wrong tool, insufficient context).

The Reframe

The iteration trap is really a clarity trap. You iterate because you don’t know what you want.

If you find yourself iterating without reading, stop and ask: “What would make the next output obviously acceptable or obviously unacceptable?”

If you can’t answer that, you’re not ready to iterate. You’re ready to think.

Takeaway

  • Iteration without criteria is just busy work
  • The moment you hope for magic, stop
  • Define what “done” looks like before you start
  • If you can’t articulate what’s wrong, the problem isn’t the output - it’s your clarity