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The Value Of Uncertainty With Simone Stolzoff – This Week’s Thinking With Mitch Joel Conversation

Episode #1037 of Thinking With Mitch Joel is now live.

This conversation with Simone Stolzoff gets into something that feels especially hard to sit with right now: the world keeps promising us more answers, more forecasts, more optimization, more certainty… and yet so many people feel more anxious, more fragile and less able to live with the unknown.

Maybe the problem is not uncertainty itself. Maybe the problem is that we have forgotten how to tolerate it.

Simo has been exploring this territory for years. He is a journalist whose work has appeared in publications like The Atlantic, and the bestselling author of The Good Enough Job, a book that challenged the way so many of us fuse our work with our identity. His new book, How To Not Know – The Value Of Uncertainty In A World That Demands Answers, takes that inquiry even further. It asks what happens when a culture built around prediction, control and optimization runs into the very human truth that much of life remains unknowable. What makes Simo’s work land is that he is not romanticizing confusion or pretending that uncertainty feels good. It mostly doesn’t. It can feel destabilizing, especially in a world where every question seems one search query away from an answer and every platform has learned to reward confidence over humility. The harder idea is that certainty itself has become both a cultural obsession and a commercial product. We buy it from experts, algorithms, markets, pundits, productivity systems and political tribes. We crave the person who sounds sure.

But life keeps refusing to be that clean.

In this conversation, Simo and I talk about work, ambition, entrepreneurship, politics, AI, climate anxiety, relationships, creativity and the strange paradox of modern comfort. Despite unprecedented prosperity, information and connectivity, many people feel less resilient in the face of ambiguity. We also get into Brian Eno, venture capital, risk, rigidity, false certainty and why action itself can sometimes be the antidote to anxiety. Mostly, this is a conversation about learning to move without the guarantee. To make decisions without perfect information. To understand that not knowing is not always a weakness… sometimes it is where possibility begins.

The episode is now live. Listen to my conversation with Simone Stolzoff here: The Value Of Uncertainty With Simone Stolzoff – TWMJ #1037.

Before you go… ThinkersOne is a new way for organizations to buy bite-sized and personalized thought leadership video content (live and recorded) from the best Thinkers in the world. If you’re looking to add excitement and big smarts to your meetings, corporate events, company off-sites, “lunch & learns” and beyond, check it out.

Mitch Joel

Mitch Joel lives at the intersection of technology, business transformation and consumer culture. He is the Executive Director of Next Era Institute, a strategic intelligence platform helping leaders understand the forces reshaping business, technology, culture and society. The Institute identifies which shifts matter, explores their wider significance and translates them into strategic direction and momentum. Mitch is also a globally recognized keynote speaker. He has delivered thousands of presentations across both B2B and B2C industries to organizations including Google, Walmart, LEGO, Shopify, Microsoft, Procter & Gamble and Unilever. Strategy Magazine has called him “one of North America’s leading visionaries.” Mitch built his career by working directly inside the waves of change that reshaped modern business. He founded and built a digital marketing agency that worked with some of the world’s largest brands and was later acquired by WPP, where he served as President of a firm operating in 25 countries with almost 3,000 employees. Mitch is the bestselling author of Six Pixels of Separation and CTRL ALT Delete, and the host of Thinking With Mitch Joel, one of the longest-running business podcasts in the world. His writing and commentary appear in outlets including Harvard Business Review, Fast Company and Inc. Magazine. He is a member of Dr. Marshall Goldsmith’s 100 Coaches and was named to the Thinkers50 Radar. Mitch also hosts Groove – The No Treble Podcast, documenting the oral history of electric bass players. Mitch is also Co-Founder of ThinkersOne, a platform that enables companies to bring personalized thought leadership from world-class experts into meetings, events and off-sites in focused 15-minute bursts.