Summary
Overview
Jordan Harbinger interviews Simone Stolzoff about humanity's uncomfortable relationship with uncertainty. They explore why we crave certainty even when it makes us worse at decision-making, how experts can be less accurate than dart-throwing chimpanzees at predictions, and why our intolerance for uncertainty is declining in the smartphone era. The conversation covers practical strategies for building uncertainty tolerance, avoiding certainty traps like comfort, hubris, and control, and learning to make decisions despite doubt. Stolzoff shares compelling examples from business leaders like Brian Chesky and Stewart Butterfield who thrived by embracing uncertainty rather than avoiding it.
The Year of Living Dangerously: An Experiment in Relationship Uncertainty
Stolzoff opens with the story of a married couple who, after 17 years together, decided to take a year apart as an experiment rather than simply breaking up or staying together. This unconventional approach illustrates the difference between seeking certainty and turning toward uncertainty. The discussion explores whether this was brave or simply avoiding a hard decision, and reveals how people respond to uncertainty through either gathering excessive information or acting impulsively—both attempts to escape discomfort.
- A couple married 10 years, together 17, decided to take a year apart as an experiment rather than breaking up
- Intolerance of uncertainty leads to either gathering excessive information or acting impulsively, like trying on every pair of jeans or buying the first pair
- Professional uncertainty (not knowing if you'll lose your job) takes a similar toll on health as actually losing your job
" Commitment is healthiest not in the absence of doubt, but in spite of doubt. "
" The version of yourself that will handle that tragic situation, if or when it occurs, will be born into existence in that moment. And that version of you will have more context, more information, and be better equipped to handle that tragic event than the version of you today. "
Why Humans Are Obsessed With Certainty (And Terrible at Predictions)
The conversation explores our biological wiring for certainty, which evolved when uncertainty could be lethal but now applies to trivial modern decisions. Stolzoff discusses Phil Tetlock's famous research showing that expert predictions are roughly as accurate as a dart-throwing chimpanzee, yet we remain attracted to confident predictions. The rise of smartphones and instant information has decreased our tolerance for uncertainty while simultaneously bringing the world's uncertainties into our pockets, creating a problematic mismatch.
- Our ancestors needed certainty for survival—not knowing if fruit was poisonous or what rustled in bushes could be lethal
- Phil Tetlock's decade of research found the average expert was roughly as accurate as a dart-throwing chimpanzee at predictions
- The rise of mobile phones correlates with increasing intolerance of uncertainty, robbing us of practice sitting with what we don't know
- All five highest points of uncertainty in the world (since the 1980s study began) have occurred in the last five years
" Any prediction about the future is not certain by definition. It is some level of chance. "
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