DiscoverThe OptimistWhat Are You So Afraid Of? Ben Sharf on Fear, Failure, and Feeling Like You’re Never Enough
What Are You So Afraid Of? Ben Sharf on Fear, Failure, and Feeling Like You’re Never Enough

What Are You So Afraid Of? Ben Sharf on Fear, Failure, and Feeling Like You’re Never Enough

Update: 2025-08-05
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Ben Sharf is a Division 1 athlete turned founder, creator, and podcast host. But behind his calm confidence is a story of deep insecurity, fear of failure, and the relentless pressure to always do more.


In this raw conversation, we dive into:

  • The injury that derailed his hockey career and changed his identity


  • How one phone call almost made him quit the sport forever


  • Why high-achieving men are often the most insecure


  • Social media, self-worth, and chasing validation in public


  • Why success still doesn’t feel like success


  • His evolving relationship with therapy, presence, and masculinity


This episode is for the guy who feels like he should be happy, but can’t quite figure out why he still feels behind.


You don’t have to white-knuckle your way through life. You’re not alone.

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What Are You So Afraid Of? Ben Sharf on Fear, Failure, and Feeling Like You’re Never Enough

What Are You So Afraid Of? Ben Sharf on Fear, Failure, and Feeling Like You’re Never Enough

Jake Hurwitz