When Being Good at Your Job Makes You a Bad Person (Episode 193)

Jul 22, 2025

What happens when professional excellence clashes with personal virtue? Dive into the complexities of ethical decision-making, exploring modern dilemmas faced by activists, CEOs, and lawyers. The discussion reveals how roles can challenge our moral compass and examines Machiavelli's views on power versus ethics. Solutions include prioritizing roles and breaking virtue into manageable parts. Ultimately, it provokes thought on maintaining integrity while navigating societal expectations and the harsh realities of various occupations.

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ANECDOTE

Machiavelli's Political Leadership

Machiavelli argued that political leadership may require cruelty and deception.
He believed these acts can secure longer-term benefits for subjects, challenging classical virtue ethics.

INSIGHT

Role Excellence vs Virtue

Some roles require traits seemingly opposed to virtue like cruelty or aggression.
Being the best in a role like prince or CEO might mean forsaking traditional virtue for effectiveness.

ANECDOTE

Modern Role Conflicts Examples

Activists may use propaganda and scapegoats for just causes, conflicting with traditional justice.
Bosses, journalists, and others face role conflicts between job demands and moral virtues.

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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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https://ancientlyre.com/

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