Podcst

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

Financial Feminist

Her First $100K

May 12, 2026

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.


Intro

Why Uncertainty Feels Worse Than Bad News

Three Certainty Traps: Comfort, Hubris & Control

Why We Struggle to Admit We Were Wrong

Identity, Doubling Down & Changing Your Mind

Why Our Tolerance for Uncertainty Is Declining

More Information, More Anxiety

Escalating Commitment

Stop Loss Strategies & Rules-Based Decision Making

Outsourcing Your Willpower & Knowing Your "Enough"

Connie & Andrew's "Year of Living Dangerously"

How to Run Your Own Low-Stakes Life Experiment

One-Way Door vs. Two-Way Door Decisions

Ghost Ships: Making Peace with the Paths Not Taken

The Miscarriage, the Uncertainty & Finding Your Anchors

How to Not Know

Learn more about your ad choices. Visit megaphone.fm/adchoices

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