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

Sometimes in life, we choose the wrong path. When we feel like we're living a lie, it's hard to know what to do next.

That’s where Suzy Welch comes in. She’s obsessed with helping people create lives worth living. A professor at NYU’s Stern School of Business, Suzy teaches a popular class called “Becoming You,” where she takes students down a brutal, but liberating, journey to live as their authentic selves.

According to Suzy’s research, purpose is the key to unlocking the real you, but finding that purpose is often trickier than we imagine.I had a blast talking, and debating, with Suzy about what it means to craft a purpose-driven life. In this conversation, she shares with me the difference between passion and aptitude, the reason luck is overrated, and why so many people struggle to know their own values.

To learn more about Suzy and her work, check out:

her book, Becoming You

and The Becoming You Podcast with Suzy Welch

*Please note: At 9:01, Simon and Cory have a discussion about suicide.

What happens after we attain success and glory? Where do you go when there's nowhere left to run from yourself?

In Part 2 of my conversation with Cory Richards, Cory explains why reaching the summit of Everest marked the beginning of a long, painful fall from grace.

After his tumultuous decision to retire from climbing, Cory found himself lost and confused about his true identity. At the same time, he was forced to grapple with multiple life-shattering events at once -- some of his own making.

In this episode, we discuss the difference between identity and purpose, the skills Cory learned to cope with multiple tragedies, and why the more we ignore life’s harshest lessons, the louder they become.

Listen to Part 1 here or watch it on YouTube.

This…is A Bit of Optimism.

For more on Cory Richards and his work, check out:

coryrichards.com