The Art of Charm

Why You Feel Stuck in Life | Simone Stolzoff

11 snips
May 11, 2026
Guest
Simone Stolzoff
Simone Stolzoff, journalist and author of How to Not Know, explores why certainty fuels anxiety and avoidance. He discusses experts' poor forecasts, AI-driven information traps, and the comfort, control, and hubris pitfalls that keep people stuck. Short, actionable ideas about taking steps, practicing curiosity, and trusting your future self are highlighted.
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ADVICE

Don't Outsource Your Thinking To AI

  • Avoid outsourcing difficult personal thinking to AI or endless information consumption; sit with uncertainty instead.
  • Simone cites an MIT study where AI-assisted essays left students with no memory of what they wrote to show learning is lost when we skip the wrestle.
ANECDOTE

Year Of Living Dangerously Relationship Test

  • Simone recounts a couple who tested their relationship with a "year of living dangerously" experiment, separating for a year then deciding.
  • He uses the example to show prototyping uncertainty can create a third option beyond staying or leaving.
ADVICE

Build Tolerance With Small Uncertain Moves

  • Practice uncertainty exposure therapy by deliberately entering small unknowns to build resilience.
  • Simone recommends small acts like striking up conversations or trying new foods to keep your tolerance from atrophying.
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