Why You Stay Stuck in Jobs, Relationships, and Financial Patterns That Aren’t Working with Simone Stolzoff

May 12, 2026

AI Summary

5 min read

Why Uncertainty Feels Worse Than a Guaranteed Shock

People who had a 50% chance of receiving a painful electric shock were more stressed than people who knew they were definitely going to get shocked. That finding, which opens Simone Stolzoff's conversation with host Tori Dunlap, gets at the central puzzle of his new book How to Not Know: humans are wired to prefer a known bad outcome over an unknown one, and this wiring keeps us stuck in jobs, relationships, and financial patterns that aren't working.

The Three Certainty Traps

Stolzoff identifies three "certainty traps" that explain why people stay in situations they know are failing them. The first is comfort—the reassurance of the familiar, even when the familiar is bad. The second is hubris, the unwillingness to admit we made a wrong choice, which manifests as the sunk cost fallacy: "I've already put $10,000 into this" or "I've already invested five years in this relationship." The third is control, the desire to plan every outcome rather than surrender to an unknown future.

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What you'll learn

1 (02:42) **The Electric Shock Study and Why We Stay Stuck** - Tori opens with a study showing people prefer a certain bad outcome (definite electric shock) over a 50% chance of a shock, and Simone connects this to why we stay in bad jobs, relationships, and financial patterns.
2 (04:44) **The Three Certainty Traps: Comfort, Hubris, and Control** - Simone introduces his framework for why we choose known bad outcomes over unknown possibilities.
3 (06:18) **Hubris, Sunk Cost, and the Fear of Being Wrong** - Tori and Simone dig into hubris, especially how it shows up for women as the sunk-cost fallacy in relationships, MLMs, or bad financial products.
4 (08:31) **Outsourcing Certainty to Gurus and Black-and-White Advice** - The conversation turns to how people seek certainty from external sources like financial gurus or wellness influencers.
5 (11:47) **Why Our Tolerance for Uncertainty Is Declining** - Simone explains the research showing that our ability to handle uncertainty is getting worse over time.
6 (14:35) **Certainty Closes the Mind; Uncertainty Keeps It Open** - Simone states the core thesis of his book and discusses the problem with expecting certainty in every life experience.
7 (20:01) **Escalating Commitment and the Mount Everest Rule** - Simone explains the psychological phenomenon of escalating commitment and offers a practical tactic to counter it.

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Guests on this episode

Simone Stolzoff Tori Dunlap

Show Notes

Why do we stay in jobs, relationships, and financial patterns we know aren't working? Author and journalist Simone Stolzoff is back on the show to talk about his new book, How to Not Know — and the surprising answer has everything to do with our relationship with uncertainty. We're getting into the three certainty traps keeping you stuck, why more information is actually making your anxiety worse, the difference between one-way and two-way door decisions, and what it really takes to break the cycle when you can see the problem but can't seem to move. This is one of the most powerful conversations we've had on this show, and one you'll want to send to everyone you know.

Simone’s links:

How to Not Know: https://bookshop.org/a/90037/9781324089452

Learn the exact strategies to save money, pay off debt, improve your money mindset, increase your net worth, in The $100K Club. Get the details here: ⁠https://herfirst100k.com/ffpod⁠.

00:00 Intro

01:08 Why Uncertainty Feels Worse Than Bad News

03:14 Three Certainty Traps: Comfort, Hubris & Control

04:49 Why We Struggle to Admit We Were Wrong

05:36 Identity, Doubling Down & Changing Your Mind

10:23 Why Our Tolerance for Uncertainty Is Declining

14:28 More Information, More Anxiety

16:18 Escalating Commitment

16:52 Stop Loss Strategies & Rules-Based Decision Making

20:13 Outsourcing Your Willpower & Knowing Your "Enough"

28:08 Connie & Andrew's "Year of Living Dangerously"

30:21 How to Run Your Own Low-Stakes Life Experiment

35:16 One-Way Door vs. Two-Way Door Decisions

44:39 Ghost Ships: Making Peace with the Paths Not Taken

50:39 The Miscarriage, the Uncertainty & Finding Your Anchors

54:54 How to Not Know

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