Companion videos

Using AI to stress-test decisions: frameworks, trade-offs, and counterarguments — companion videos

The article uses AI as a structured sparring partner for listing options, surfacing counterarguments, and recording uncertainty without outsourcing the decision. The video below demonstrates related prompts and also discusses where generated coaching stops being useful.

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36:42
I Tried AI as a Life Coach for 365 Days - Here's What I Learned

Ali Abdaal

Lays out related challenge prompts ("give me the steelman counterargument," "give me a scathing critique"), explanatory theories, and the Solomon method (have the AI play your 90-year-old self). It also names boundaries around mental health and accountability, matching the article's use of generated advice as one input rather than a decision.

What you should get from this: Use AI to challenge assumptions, compare options and surface counterarguments before making decisions.

Watch or know first: None — bring a decision you're actually wrestling with.

AI Expert note: He's candid about where AI stopped being useful — mental health and accountability — and that boundary is as much the point as the prompts; it matches the article's thinking-partner-not-oracle framing.

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