What if Uncertainty Isn’t Such a Bad Thing?

The Next Big Idea55mMay 14, 2026

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AI-Generated Summary

In this episode of The Next Big Idea, hosts Caleb Bissinger and Rufus Griscom explore the transformative power of embracing uncertainty, featuring author Simone Stolzoff, whose new book 'How to Not Know' argues that uncertainty is not a threat but a gateway to growth, creativity, and authentic living. Drawing on personal stories, psychological research, and real-world examples—from the founder of Slack who pivoted from a failing game to building a $27 billion company, to a professor teaching students that 'it's okay to say I don't know'—the conversation dismantles the myth that certainty equals control. The hosts and guest examine how overplanning, driven by childhood trauma and the digital age’s instant answers, leads to paralysis and missed opportunities. They also explore the paradox of expertise: the more skilled we become, the more rigid our thinking, and how institutions like the Federal Reserve have created 'Departments of Doubt' to counteract this. Ultimately, the episode champions a mindset of 'the next right action,' embracing ambiguity as a source of joy, possibility, and deeper connection to life.

Key Takeaways
1

Uncertainty is not a problem to be solved but a condition to be embraced as a source of growth and creativity.

2

Overplanning and the pursuit of false certainty can lead to paralysis and prevent us from taking meaningful action.

3

The most credible leaders are those who admit what they don’t know and persist anyway.

4

Taking the 'next right action'—not a five-year plan—is more effective than trying to predict the future.

5

The 'ghost ship' metaphor reminds us that every choice we make means letting go of other possible lives, and peace comes from accepting that.

…and 2 more takeaways available in PodZeus

Chapters
0:00
10 min

The Crisis of Certainty in a Chaotic World

We would rather know a certain bad thing is happening than have to reckon with the ambiguity.

Highlight
10:00
10 min

The Psychology of Planning and Paralysis

Caleb shares his own struggle with overplanning, rooted in childhood instability from his parents’ divorce. Simone explains how this behavior, while protective, can block joy, spontaneity, and growth. The episode explores the two extremes of uncertainty intolerance: obsessive information-gathering and paralysis.

20:00
10 min

The Rise of Digital Certainty and the Erosion of Patience

By reaching into our pockets to answer each and every one of our questions, it robs us of the practice of sitting with what we don't know.

Highlight
30:00
10 min

From Failure to Fortune: The Slack Story

It was his willingness to turn toward his uncertainty that allowed him to discover something that was greater than what he could have ever anticipated.

Highlight
40:00
10 min

The Art of the Next Right Action

Make a choice relatively quickly and then spend your energy convincing yourself of the reasons why you made that choice.

Highlight
High-Impact Quotes
Stay open forever. So open it hurts and then open up some more until the day you die world without end. Amen.
George Saunders (quoted by Simone)48:52
Viral: 95.0
We are open, we are open, we are open.
Simone Stolzoff47:46
Viral: 92.0
It was his willingness to turn toward his uncertainty that allowed him to discover something that was greater than what he could have ever anticipated.
Simone Stolzoff16:03
Viral: 90.0
Speakers

Hosts

Caleb BissingerRufus Griscom

Guest

Simone Stolzoff
Topics Discussed
uncertainty tolerance95%the next right action92%planning and overplanning90%decision-making under ambiguity88%expertise and cognitive bias85%emotional resilience in loss82%the role of doubt in innovation80%digital age and instant answers78%
People & Brands

Caleb Bissinger

person

15xPositive

Rufus Griscom

person

14xPositive

Simone Stolzoff

person

12xPositive

Slack

product

5xPositive

Max

person

4xNeutral

Stuart Butterfield

person

4xPositive

Federal Reserve

organization

4xPositive

Department of Doubt

organization

4xPositive

Ruth Chang

person

4xPositive

TinySpec

organization

3xNeutral

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