Sometimes in life, we must stop and ask ourselves, “Where am I you going next?” Other times, it’s more fun to do a podcast takeover.

No one has ever interviewed me quite like Cal Fussman. Cal has a gift – he pulls things out of you that you didn’t even know were there. A prolific Writer At Large for Esquire, Cal has interviewed legends like Muhammad Ali and Mikhail Gorbachev, and he’s the host of the podcast Big Questions. So, to mark 15 years since writing Start With Why, I invited Cal to take over my podcast and ask me the questions I don’t usually get asked.

Cal did get me to open up in this conversation, but not in the way you might expect. We talk about where I’ve been, where I’m going, the infinite game, creativity in AI…and why I’ve become so obsessed with friendship lately.

This…is A Bit of Optimism

For more on Cal and his work, check out:

Big Questions with Cal Fussman

Where Is Simon Going? with journalist Cal Fussman 50:18 Share

A Bit of Optimism

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Where Is Simon Going? with journalist Cal Fussman