The Jordan Harbinger Show 1326: Simone Stolzoff | How to Make the Most of Uncertainty
35 snips
May 12, 2026 
Simone Stolzoff, author and journalist who studies uncertainty and decision‑making. She explores why we cling to false certainty, how our brains misjudge risk, and common traps like comfort and hubris. Short, practical ideas include training uncertainty tolerance with micro‑experiments, using values as anchors, and decision heuristics for messy choices.
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Use Certainty Anchors To Hold Uncertainty
- Find certainty anchors like values, location, or rituals to hold while other areas stay uncertain.
- Simone used Airbnb's Brian Chesky example: define principles (e.g., keep stakeholders in mind) to guide pandemic decisions.
Glitch Pivot Gave Birth To Slack
- Tiny Speck shut down its hit game Glitch at peak and repurposed an internal tool into Slack.
- Founder Stuart Butterfield pivoted, made investors whole, and turned a communication feature into a $27.5B acquisition.
Ambiguity Feels Worse Than Certain Pain
- People prefer known pain over ambiguous risk; 50% chance of shock produces more stress than certain shock.
- Anticipatory uncertainty (like job insecurity) harms health similarly to actual job loss.
