How to Deal with Uncertainty (and Stop Overthinking Everything) | Simone Stolzoff

Marriage Kids and Money: Personal Finance for Families

Andy Hill

Investing, Business, Kids & Family, Parenting

4.9 • 604 Ratings

🗓️ 20 May 2026

⏱️ 26 minutes

🔗️ Recording | iTunes | RSS

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Summary

Simone Stolzoff’s new book: How to Not Know - ⁠https://amzn.to/420WLhp⁠ (affiliate) Uncertainty is everywhere right now. From economic shifts and global conflict to career changes and parenting decisions, many of us are craving answers in a world that feels increasingly unpredictable. In this episode, we sit down with author and journalist Simone Stolzoff to discuss how we can become more comfortable with uncertainty instead of constantly trying to eliminate it. Simone shares insights from his new book, How to Not Know: The Value of Uncertainty in a World That Demands Answers, and explains why our obsession with certainty may actually be fueling anxiety. We discuss how technology has changed our tolerance for the unknown, why discomfort can lead to growth, and practical ways to build resilience in uncertain times. If you’ve been feeling overwhelmed by the future, this conversation will help you slow down, breathe deeper, and rethink your relationship with uncertainty. RESOURCES Own Your Time – Pre-order our first book today! MKM Coaching – Get 1-on-1 support with your family finance journey. Coast FIRE Calculator – Find out when you can slow down or stop investing for retirement. Mortgage Payoff Calculator – See how fast you can become mortgage free. RECOMMENDED RESOURCES (SPONSORS & AFFILIATES) Monarch Money – Best budget app for families & couples. Crew – HYSA banking built for families (Get an extra 0.5% APY with our partner link). GUEST RESOURCES Simone Stolzoff’s new book: How to Not Know - https://amzn.to/420WLhp HOW WE MAKE MONEY + DISCLAIMER This show may contain affiliate links or links from our advertisers where we earn a commission, direct payment or products. Opinions are the creators alone. Information shared on this podcast is for entertainment purposes only and should not be considered as professional advice. Marriage Kids and Money (www.marriagekidsandmoney.com) is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to amazon.com. CREDITS Host: Andy Hill Editor: Johnny Sohl Podcast Support: Michelle Ahmed Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	This episode is sponsored by my new book, Own Your Time.
0:03.0	I wrote it for parents who are doing everything right on paper, but still feel stretched thin.
0:07.8	Own Your Time gives you a clear path to take back control of your money, your work, and your family time.
0:13.5	Find it on Amazon or Barnes & Noble.
0:15.8	Own Your Time by Andy Hill.
0:19.0	Striking up a conversation with a stranger, or maybe taking a new route to work, or ordering
0:24.5	something that you would normally order on a menu.
0:27.5	These might not seem like very big things that will make a difference in the larger questions
0:32.8	of your life, but the research shows that these little exposures to uncertainty can rewire our brain to make us more comfortable and tolerant of uncertainty.
0:45.3	This show is dedicated to helping you, strengthen your family tree, and live financially free. Welcome to the Marriage Kids and Money podcast, everybody.
0:54.9	This is Andy Hill.
0:56.2	And today we're talking about how to deal with uncertainty.
0:59.5	To help us discuss this challenging topic, I've invited Simoney Stolesoff back on the show today.
1:05.1	Simone is an author and journalist who explores big questions about work, meaning, and identity.
1:10.7	A former design lead at
1:13.1	Global Innovation Firm IDEO, he is the author of two books, The Good Enough Job, and now his latest,
1:20.4	How to Not Know the Value of Uncertainty in a World that Demands Answers. And when he's not
1:26.4	exploring work, meaning, and identity, he enjoys spending time with his wife and son in San Francisco. Welcome back to the show, Simone. Thanks for having me back. Absolutely, man. I'm glad to have you back and have this great discussion. We had a great one during your last book tour, a good enough job, and I really enjoyed that conversation. So let's dive into this
1:44.6	conversation of uncertainty. Why do you think we're living in a moment of great uncertainty?
1:49.7	Here's the part where I throw up my hand and say, I don't know. Just kidding. Yeah, I mean,
1:54.8	there's data that has showed basically in the last four decades or so. The five highest measurements
2:00.1	of uncertainty have all occurred in the last five years or so, the five highest measurements of uncertainty have all occurred
	...

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