1326: Simone Stolzoff | How to Make the Most of Uncertainty

What It Covers

Simone Stolzoff, author of *How Not to Know*, joins Jordan Harbinger to examine why humans are biologically wired to crave certainty, how that craving produces worse decisions in modern life, and what concrete tools — from running small experiments to identifying certainty anchors — help people make sound choices despite unavoidable ambiguity across careers, relationships, and identity.

Key Questions Answered

• •Uncertainty Tolerance Training: Build comfort with uncertainty through graduated exposure, the same way phobia treatment works. Start with low-stakes novelty — ordering an unfamiliar dish, taking a new route to work, talking to a stranger. Each micro-dose rewires the brain's threat response to ambiguity, making it easier to hold larger, unresolved uncertainties in career or relationship decisions without defaulting to impulsive or avoidant behavior.
• •One-Way vs. Two-Way Door Decisions: Jeff Bezos's framework distinguishes permanent decisions (buying a house, marriage) from reversible ones (most career experiments, side projects). The critical error is applying the exhaustive analysis of a one-way door to a two-way door choice. Doing so wastes time and kills opportunity. When a decision can be course-corrected, move faster, act, and let real-world feedback replace desk research and endless deliberation.
• •Expert Prediction Accuracy: Researcher Phil Tetlock compiled a decade of predictions from economists, politicians, and journalists and found average expert accuracy roughly matched a dart-throwing chimpanzee. Confidence signals credibility socially but not statistically. The practical takeaway: weight expert opinion by their track record and stated uncertainty, not their conviction. Seek advisors who explicitly name what they don't know alongside what they do.
• •Certainty Anchors Under Pressure: When facing major uncertainty in one life domain, deliberately identify fixed points in others — known location preferences, relationship commitments, role type — to reduce cognitive load. Airbnb's Brian Chesky used this during COVID: he wrote down three core values before making any decisions, including spending $250 million to reimburse hosts. Clear anchors allow principled action when outcomes remain unknown.
• •The 37% Rule for Commitment: The mathematical "secretary problem" suggests interviewing roughly 37% of available options to calibrate preferences, then committing to the next candidate who meets or exceeds that benchmark. Applied to hiring, dating, or career choices, this prevents both premature closure and endless optimization. Once you know your rubric, continued optionality-seeking produces diminishing returns and measurable decreases in satisfaction and decision quality.
• •Three Certainty Traps: Stolzoff identifies comfort (staying safe, avoiding exposure), hubris (overconfidence in one's own predictions), and control (over-planning future outcomes) as the three primary traps that make uncertainty worse. Each has a corresponding corrective: growth requires leaving comfort zones, humility requires admitting ignorance openly, and acceptance requires distinguishing controllable from uncontrollable variables using a structured separation exercise before acting.
• •Trust Your Future Self: When catastrophizing about a potential bad outcome — job loss, relationship failure, health crisis — recognize that the version of you who faces that situation will have more context, more information, and more adaptive capacity than your current self. This reframe, drawn from Stolzoff's therapist source Emily, reduces anticipatory anxiety and prevents over-planning for scenarios that may never materialize, freeing cognitive resources for present decisions.