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

2026-05-12 · 59 min · episode 285 · 11 entities

episode page audio

Asserted relationships

  • → appeared on Financial Feminist podcast
    0.68
    evidence rules-v5
    285. Why You Stay Stuck in Jobs, Relationships, and Financial Patterns That Aren’t Working with Simone Stolzoff
  • → discusses Business company
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    evidence rules-v5
    Feed category: Business
  • → discusses Education concept
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    evidence rules-v5
    Feed category: Education
  • → discusses Self-Improvement concept
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    evidence rules-v5
    Feed category: Self-Improvement
  • → discusses How To concept
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    evidence rules-v5
    Feed category: How To
  • → hosted by Her First $100K company
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    evidence rules-v5
    Feed author/publisher: Her First $100K

Entities found in this episode

concepts 5

  • mentioned Education concept
    0.50
    evidence rules-v5
    Feed category: Education
  • mentioned Self-Improvement concept
    0.50
    evidence rules-v5
    Feed category: Self-Improvement
  • discusses Education concept
    0.40
    evidence rules-v5
    Feed category: Education
  • discusses Self-Improvement concept
    0.40
    evidence rules-v5
    Feed category: Self-Improvement
  • discusses How To concept
    0.40
    evidence rules-v5
    Feed category: How To

companys 4

  • mentioned Her First $100K company
    0.70
    evidence rules-v5
    Feed author/publisher: Her First $100K
  • mentioned Business company
    0.50
    evidence rules-v5
    Feed category: Business
  • discusses Business company
    0.40
    evidence rules-v5
    Feed category: Business
  • hosted by Her First $100K company
    0.40
    evidence rules-v5
    Feed author/publisher: Her First $100K

persons 1

  • mentioned Simone Stolzoff person
    0.72
    evidence rules-v5
    285. Why You Stay Stuck in Jobs, Relationships, and Financial Patterns That Aren’t Working with Simone Stolzoff

podcasts 1

  • appeared on Financial Feminist podcast
    0.68
    evidence rules-v5
    285. Why You Stay Stuck in Jobs, Relationships, and Financial Patterns That Aren’t Working with Simone Stolzoff
Episode description as stored
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 Learn more about your ad choices. Visit megaphone.fm/adchoices