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How to ThinkIn the Age of AI

Identify the deepest assumption in each decision domain…

For each major domain where you make decisions, explicitly write down the single deepest assumption everything else depends on, then list 5-10 decisions that would change if that root were different to verify you've found an actual root.

When This Fires

  • During deep self-reflection about major life or career domains
  • When multiple decisions in the same domain keep producing unsatisfying results
  • During strategic reviews when questioning foundational premises
  • When you suspect a systematic error in a decision domain but can't identify the source

Common Failure Mode

Identifying a mid-level assumption as the root: "My deepest career assumption is that I should work at startups." But why startups? "Because I value autonomy." Why is autonomy the priority? "Because I believe the best work comes from self-directed people." That last statement is closer to the root — and changing it would cascade through career decisions, management style, collaboration preferences, and work environment design.

The Protocol

For each major decision domain: (1) Write: "The single deepest assumption underlying my decisions in [domain] is: [one sentence]." (2) Verify: list 5-10 specific decisions that would change if this assumption were different. (3) If fewer than 5 decisions would change → you haven't found the root. Ask "why do I believe this?" and go deeper. (4) If 5-10+ decisions would change → you've found a genuine root assumption. Now evaluate it: is this assumption well-supported? Has it been tested? When was it last examined? Root assumptions that cascade through many decisions deserve the most rigorous scrutiny.