Running goals through a gauntlet

Winkletter  •  11 Aug 2026   •    
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Goals have gaps. Dreams always begin in a fog, and it’s a rose-colored fog. At some point, though, the dream meets reality and reality steps on the dream’s face.

I’ve been working on a new step for research. When considering a goal, I run the idea through a gauntlet first. The gauntlet is a set of report prompts. I have AI imagine a representative persona has pursued the goal, built the product, or published the research and then it generates a set of documents. Some are friendly, others adversarial. But it builds out a set of documents purpose-built for different rhetorical situations. It imagines what the future might hold through different lenses that focus on a specific dimension.

  • A workshop plan takes the idea and operationalizes it.
  • A group chat transcript imagines the strain on friends and family.
  • A Kickstarter postmortem considers the hidden costs of building and shipping a product.

That in itself is informative. But this material can also feed into a research step. And I find it widens the problem space where the AI researches. It’s basically adding imagination to project research to prepare for many different potential futures.

  • The Gauntlet: If you want to try it out, I generated a little tool to list the report prompts based on three different types of goals: personal futures, product & ventures, or published arguments

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