Toughness Found on the Road

If at some point, you've looked at your life—your job, your relationships, your achievements—and thought: “is this it?” This episode is for you. 

Mike Posner had that moment at 30. His life, by every external measure, was extraordinary: he had hit songs, Grammy nominations, millions in the bank. He was a pop star… And he was miserable.

What followed was one of the most honest reckonings we've ever heard on this show. Mike walked across America, survived a rattlesnake bite, climbed Everest, and came out the other side with something no amount of success had ever given him: peace.

Mike Posner is a multi-platinum, Grammy-nominated recording artist, songwriter, and producer. But the reason you should listen to this conversation has nothing to do with any of that. It has everything to do with where he was and his incredibly human journey getting to somewhere better, more peaceful, and more meaningful. He even wrote a song about it—a follow up to his hit song “I Took a Pill in Ibiza” called “I Went Back To Ibiza.”

In this episode you'll learn:

➡️ Why achieving your biggest goals can leave you feeling emptier than before you started 

➡️ The difference between real vulnerability and broadcasting your pain online (and why intention changes everything) 

➡️ Why comfort (not failure) might be the thing quietly hollowing out your life 

➡️ What walking across America actually taught Mike about who he was and who he wasn't 

➡️ Why self-improvement taken too far becomes selfishness 

➡️ The one pursuit more valuable than success, grit, or getting to the top

You don't need a Grammy nomination to relate to this conversation, you just need to have ever wondered if the life you're building is actually the life you want.

This… is A Bit of Optimism.

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Watch A Bit of Optimism on Spotify! If you’re subscribed to Spotify Premium, you don’t get any Spotify ads on my video.

If you want to watch Mike’s new music video for “I Went Back To Ibiza,” check it out here: https://www.youtube.com/watch?v=UDL6SEW4xKU

You can find “I Went Back To Ibiza” wherever you stream music.

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Chapters

Chapters

• 00:00:00 The Real Reason You Feel Empty
• 00:06:51 Art as Alchemy: Turning Pain into Beauty
• 00:18:12 The Asymmetry Between What We Have and What We Give
• 00:20:32 Walking Across America: Getting Out of His Comfort Zone
• 00:24:54 The Snake Bite: When Attention Came From Pain
• 00:30:13 The Problem With Avoiding Discomfort
• 00:33:47 From Fraud to Peace: Mike's Transformation
• 00:36:31 Walking Each Other Home: The Purpose of Art and Life
• 00:38:56 The Pursuit of Peace, Not Just Hardship
• 00:48:48 Getting to the Top of Everest: Only Half of the Journey

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Simon is an unshakable optimist. He believes in a bright future and our ability to build it together.

Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do.

Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game.

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