Jon and Peter tackle two challenges facing successful entrepreneurs: being truly present with family despite physical attendance, and navigating career transitions without severing valuable connections.

Ever felt "a million miles away at work” when spending time with family? You’re not alone. It’s a common paradox that many an entrepreneur has to deal with. That “paradox” of being present in body when you’re out with family, but absent in mind because all you’re thinking about is work.

The entrepreneurial personality that drives business success (obsessive, curious, relentless) becomes the enemy of presence. Entrepreneurs often swap one addiction for another: trading work obsession for ultramarathon training or school board positions, still pressing the gas pedal instead of learning to simply be.

Peter introduces the framework of quality versus quantity time. Having household help isn't about avoiding parenting. It enables better engagement during hours spent together. And it’s not an easy transition for entrepreneurs. Imagine building and managing "palaces of business operations" where everything bends to their control, then returning home where nothing does.

On career transitions, Jon argues against two extremes. Don't make your next chapter entirely about your previous identity (the Navy SEAL who only does SEAL ventures), but don't abandon it completely either. The answer is to "reinvent yourself 25% at a time" by leveraging your background to open doors while building toward something new.

Peter adds Charlie Munger's principle: "The first rule of compounding: Never interrupt it unnecessarily," especially regarding relationships. That fraternity photo from twenty years ago? Those shirtless beer-drinking kids are now senior lawyers, venture-backed founders, and doctors. That makes for an invaluable network that compounds over decades.

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