meta_pixel
Tapesearch Logo
Log in
Financial Feminist

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

Financial Feminist

Her First $100K

Education, Self-improvement, Business, How To

4.76.6K Ratings

🗓️ 12 May 2026

⏱️ 61 minutes

🧾️ Download transcript

Summary

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

Transcript

Click on a timestamp to play from that location

0:00.0

We just got done recording today's episode. It was one of the most powerful conversations we've had on this show. And as you can tell, if you're watching on YouTube, this episode deeply moved me. And I think it'll deeply move you too. Today we are talking about uncertainty. And this is uncertainty that makes us deeply uncomfortable as humans. It's uncertainty about the worlds and politics and the economy.

0:23.0

It's uncertainty about our relationships.

0:25.8

It's uncertainty about not knowing if we are on the right path.

0:29.2

Today's guest is a repeat guest, and we loved him so much we brought him back on the show.

0:33.5

Simone Stolsoff is an author and journalist who has spent his career asking the questions no one wants to sit with.

0:39.7

He's the author of two books, The Good Enough Job, which we talked about the first time he was on this show.

0:44.0

It is the number one work-life balance bestseller that's been translated into over a dozen languages.

0:50.1

But we're here to talk about his new book, How to Not Know.

0:52.9

Right off the top, I will give you

0:54.5

a content warning that we do discuss loss and miscarriage in this episode. But this is an

1:01.0

episode you will want to listen to again and again and send to people in your life to talk about

1:05.0

too. All right, I've blubbered enough. Let's get into it.

1:13.2

But first, a word from our sponsors.

1:15.7

This podcast is sponsored by Squarespace.

1:20.1

When my partner was launching his business last year, I was like, great, you need a Squarespace website.

1:21.0

That was the first thing we did was sign up for Squarespace.

1:23.3

And we signed up on Friday using my code.

1:27.0

And by Monday, he had a brand new website and was

1:29.6

already making money. Yes, really. He used their cutting edge design tools to design a perfectly

1:34.7

navigable website, that's a word, and the ability to offer services right within Squarespace,

1:39.9

so he was not using a third-party platform. And with the analytics tools in the back end,

1:43.6

we could see exactly where people were coming from

...

Transcript will be available on the free plan in 2 days. Upgrade to see the full transcript now.

Disclaimer: The podcast and artwork embedded on this page are from Her First $100K, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Her First $100K and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.

Copyright © Tapesearch 2026.