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327 — Why You Can't Make Up Your Mind (and How to Finally Decide) with Bestselling Author Simone Stolzoff

June 23, 2026
Mentally Stronger Simone Stolzoff Amy Morin

Think about the last time you couldn’t make up your mind about a big decision. Maybe you made a pro-and-con list, read every review, and talked it through with other people — and still couldn’t decide.
 
We tell ourselves that just a little more information will finally bring the certainty we need to choose. But my guest today says more research can fuel your anxiety and the certainty we’re chasing doesn’t actually exist. If you’re indecisive, you overthink every choice, or you freeze up for fear of making the wrong decision, this episode is for you.
 
My guest is Simone Stolzoff, a journalist and the author of The Good Enough Job. His new book, How to Not Know, is all about making hard decisions and learning to tolerate uncertainty.
 
In this episode on decision-making and uncertainty, we discuss:
 

  • Why our tolerance for uncertainty is shrinking at the exact moment the world is becoming more uncertain
  • The two surprising ways people dodge hard decisions — and why impulsive decision-makers may be just as avoidant as obsessive researchers
  • The study that showed we’d rather face a guaranteed painful event than sit with the uncertainty of one
  • Why the best leaders aren’t “know-it-alls” but “learn-it-alls”
  • The Only Option Test — a fast way to break a stuck decision when both choices look equally good
  • The Chinese farmer parable, and why “maybe yes, maybe no” is one of the most freeing things you can tell yourself
  • The line from an oncology doctor that can change how you face anything uncertain in your future
  • The Therapist’s Take: my top three strategies for making decisions and living with uncertainty, starting today

 

Key Takeaways:

 

  • Rethink Decision-Making: Use the “only option test” to simplify choices between comparable options and reduce unnecessary stress.
  • Distraction as a Tool: When awaiting outcomes beyond your control, engage in activities that can distract the mind effectively.
  • Empathize with Curiosity: Shift from viewing uncertainty as a threat to seeing it as a possibility for growth and new opportunities.
  • Future Self Trust: Believe in your future self’s ability to handle future challenges to free you from present anxieties.
  • Emotional Resilience: Uncertainty can be cultivated through continuous exposure and deliberate practice.

Notable Quotes:

"Intolerance of uncertainty can underpin a lot of anxiety disorders." - Simone Stolzoff

"Uncertainty is incredibly uncomfortable...but it's by design." - Simone Stolzoff

"Trust in your future self's ability to handle your future problems." - Simone Stolzoff

Timestamp Summary

0:00 The Trap That Keeps You Stuck No Matter How Much You Research

2:18 The Two Job Offers That Sent Simone Into an Existential Spiral

4:58 Why Your Tolerance for Not Knowing Is Shrinking Right Now

9:00 The Surprising Way Impulsive People Are Secretly Avoiders Too

11:24 Why We'd Rather Take a Guaranteed Shock Than Sit With "Maybe"

19:54 Be a "Learn-It-All," Not a Know-It-All (and the Slack Story)

26:35 The "Only Option Test" That Cracks Any Tough Decision Fast

29:42 The Farmer and the Horse: Why You Can't Know What's Good or Bad Yet

35:28 The Therapist's Take: 3 Ways to Get Comfortable Not Knowing

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