Why Success Still Feels Empty for So Many Business Owners

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Why do so many business owners achieve everything they set out to build… yet still feel a quiet emptiness underneath it all?

In this conversation, Benji sits down with Philip McKernan to explore why success often feels misaligned, why old wounds silently shape our ambition, and what it takes to shift from proving yourself to actually living in alignment. This episode is a grounded, honest look at the emotional and psychological patterns entrepreneurs rarely talk about—but deeply feel.

In this episode: • Why success doesn’t guarantee fulfillment • How trauma shapes ambition and leadership • The “I’ll show you” fuel that eventually burns out • The three mountains and the cost of staying on the wrong one • How to start reconnecting with work that feels true  

Timestamps 
00:00 Opening and setup 
01:26 Why emotional alignment matters more than achievement 
04:16 How trauma quietly drives many entrepreneurs 
07:38 The danger of building a life to prove someone wrong 
11:14 Understanding ego in a healthier, more honest way 
14:26 The myth of “escape velocity” and waiting to feel free 
18:53 What it takes to step into the next mountain 
27:38 Simple first steps to reconnect with purpose