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

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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