How to Not Know: Simone Stolzoff

We have more information than any generation in history. And we're more anxious about the future than ever. So what's going wrong?

In this episode, Mina Seetharaman talks with Simone Stolzoff, journalist, author, TED speaker, and former IDEO Design Lead, about why certainty is so seductive, how our hunger for it quietly gets us into trouble, and what it actually looks like to build uncertainty tolerance as a skill.

Simone's new book, How to Not Know, draws on years of reporting to examine the three certainty traps that hold leaders back—comfort, hubris, and control—and offers practical tools for anyone navigating hard decisions, unclear direction, or rapid change. Together, Mina and Simone explore why the most resilient leaders are the ones willing to say "I don't know," how to make decisions when the path isn't clear, and a concept called ghost ships that reframes what it means to choose.

This is one of several conversations on uncertainty coming to the Creative Confidence Podcast this year. Subscribe to catch them all.

Related Resources:

How to Not Know, by Simone Stolzoff — https://simonestolzoff.com/how-to-not-know

Simone Stolzoff on LinkedIn — https://www.linkedin.com/in/simone-stolzoff-5a16b648/

Simone’s Harvard Business Review article: Leaders, It’s Time to Build Your Tolerance for Uncertainty — https://hbr.org/2026/01/leaders-its-time-to-build-your-tolerance-for-uncertainty

Read the blog recap — key ideas from this episode, plus five things to put into practice. ideou.com/blogs/inspiration

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In This Episode:

(Timestamps are approximate due to ad breaks)

(00:00) Welcome and introducing Simone Stolzoff

(03:21) From The Good Enough Job to How to Not Know — the thread between his two books

(05:48) Why uncertainty feels like a threat — the biology behind it

(09:37) Rowing through the fog — what Simone learned at IDEO

(12:17) Why certainty has a narrowing effect on creativity

(15:12) Commitment in spite of doubt — the Rollo May quote

(16:19) The Slack origin story — how Stuart Butterfield trusted his uncertainty

(18:20) Standing on a mountain peak — why you have to descend before you can go higher

(18:42) The three certainty traps: comfort, hubris, and control

(22:38) The AI prediction that aged poorly — Geoffrey Hinton and the radiologists

(25:05) More information, more anxiety — why our phones aren't helping

(30:17) The loss of friction — what we give up when we reach for our phones

(34:09) How to actually build uncertainty tolerance

(37:27) Microdosing the unknown — why small experiments rewire the brain

(42:13) Busting the algorithm — the explore-exploit tradeoff explained

(44:51) How to say "I don't know" without losing the room

(45:40) What Brian Chesky did when Airbnb's entire business shut down overnight

(49:11) Ghost ships and how to let go of the lives you didn't choose

(54:03) The difference between one-way and two-way door decisions

(56:32) What to do when you're in the middle of something genuinely hard

(57:17) Lightning round

(57:38) High Maintenance on HBO

(58:30) Brian Eno on originality

(59:02) Learning salsa dancing

(59:32) The skill of asking questions

(59:52) Leaving the Atlantic for IDEO — the mistake that wasn't

(01:00:38) Always eat the cookie

(01:01:40) Advice for a younger self

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