The Bulwark Podcast Ryan Holiday: Life Is Too Short to Be a Bootlicker
74 snips
Oct 24, 2025 
Ryan Holiday, an author and expert on Stoic philosophy, shares insights from his latest book, Wisdom Takes Work. He emphasizes the importance of opposing bootlicking in politics and how ancient wisdom remains relevant in today's landscape. Ryan discusses the dangers of echo chambers, particularly for figures like Elon Musk and Trump, noting how their media diets skew reality. He offers advice on avoiding groupthink, urging listeners to seek diverse information sources. Plus, he suggests ways to engage modern men with Stoic values.
AI Snips
Chapters
Books
Transcript
Episode notes
Timeless Courtier Behavior
- Courtiers endlessly flatter vain leaders to retain influence, repeating an ancient pattern from Roman times to today.
- Ryan Holiday sees modern aides like Stephen Miller as performing that timeless bootlicking role.
Speak Truth, Don't Bootlick
- Say what you think and refuse to be a bootlicker; express truth even when it's costly.
- Ryan Holiday argues courage and justice require speaking up against an aspirationally fascist administration.
Naval Academy Speech Canceled
- Ryan Holiday was canceled from speaking at the Naval Academy after refusing to remove slides about book removals.
- He declined to omit criticism of library censorship and pulled the talk on principle.
