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.

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