The Real Reason You Feel Empty (Even When Life Looks Good) with Musician Mike Posner

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. + + + 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: You can find “I Went Back To Ibiza” wherever you stream music. + + + 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 + + + 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. + + + Website: Live Online Classes: Podcast: Instagram: Linkedin: Twitter: Facebook:

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The Real Reason You Feel Empty (Even When Life Looks Good) with Musician Mike Posner is an episode from A Bit of Optimism by The Optimism Company from Simon Sinek.

This episode is 52:37 long.

This episode was published on May 5, 2026.

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