What happens when the roles life gives you conflict with being a good person? Caleb and Michael tackle one of Stoicism's puzzles: when excellent performance in your job, relationships, or responsibilities seems to require abandoning virtue.

Starting with Machiavelli's brutal advice to princes, they work through modern examples where this tension emerges. The activist who uses propaganda for a just cause. The CEO who fires employees for market efficiency. The lawyer defending someone they think is guilty. The journalist photographing tragedy without intervening.

The Stoics said to follow your roles, but what if your roles demand cruelty, deception, or abandoning compassion? The conversation reveals three ways to think through these conflicts.

(00:00) Introduction: When roles conflict with virtue

(03:40) Machiavelli's challenge to virtue ethics

(08:20) The difference between bad people and role conflicts

(14:30) Modern examples: activists and propaganda

(16:00) Workplace tensions: bosses and market demands

(16:30) Impartial observers: journalists and philosophers

(18:00) Best soldiers follow orders without question

(20:30) Legal defenders and the guilty client

(22:40) When roles seem necessarily at odds with virtue

(27:00) Solution 1: The Stoic hierarchy of roles

(30:00) Human role vs chosen roles

(34:20) Why hierarchy alone isn't enough

(38:50) Solution 2: Breaking virtue into sub-components

(42:00) Fair dealing depends on context and circumstances

(46:20) Practical advice for everyday conflicts

(48:00) Solution 3: Using rights and consequences as constraints

(50:40) Reserve clause and staying flexible between roles

(51:20) Why most conflicts resolve with careful thinking

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Thanks to Michael Levy for graciously letting us use his music in the conversations:

https://ancientlyre.com/

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Fresh Voices on Legal Tech with Mathew Kerbis