Stoicism with Ryan Holiday - Part 1

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Jul 26, 2025

Ryan Holiday, a bestselling author known for his works on Stoicism and marketing, joins for a deep dive into creativity and personal ethics. They explore the evolving nature of writing and podcasting, discussing the pitfalls of algorithm-driven platforms that strain authenticity. Holiday emphasizes the importance of allowing ideas to breathe without premature judgment and reflects on the challenge of balancing artistic freedom with audience expectations. The conversation reveals insights on navigating the chaotic landscape of modern discourse.

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ADVICE

Avoid Premature Project Discussion

Avoid talking about a book or project until it is well underway and you have a strong grasp of it.
Premature discussion can kill creative momentum and make your ideas sound uncertain.

INSIGHT

Social Media Creates Instant Feedback

Social media fosters immediate feedback, unlike the delayed rewards of book writing, affecting creative compulsion.
Stand-up comedy offers continuous dopamine hits from daily feedback, unlike slower creative outlets.

INSIGHT

Reconsider the Meaning of Point of View

Nowadays, 'point of view' often boils down to binary, polarized stances.
Focusing on personal growth can be more ethical than engaging in polarized debates on every issue.

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A Note from James:

Ryan Holiday is one of the few writers I consider a peer—not just because of the work he’s done, but because of the choices he's made along the way. We’ve both published a lot of books. We've both dealt with audiences, platforms, and the weight of having a “point of view” in a world that increasingly wants you to pick a side. This episode wasn’t meant to be a debate or an interview. It was just two people trying to make sense of the tension between creativity and truth, honesty and influence, and why sometimes the best thing you can say is nothing at all.

Episode Description:

In this candid and far-ranging conversation, James Altucher sits down with bestselling author Ryan Holiday to talk about the changing nature of creativity, writing, podcasting, and personal ethics in a polarized media landscape.

They discuss the illusion of having to weigh in on every issue, the danger of algorithmic thinking, and how to stay true to your voice without becoming a prisoner to your audience. Whether you're a writer, a creator, or just trying to think more clearly in chaotic times, this episode offers real insight into the forces shaping our thinking—and how to resist them.

What You’ll Learn:

Why sharing too early can kill creative momentum
How social media shifted from expression to algorithm worship
Why long-form podcasts might be bad for your brain
How writing differs from other art forms in its tension and permanence
The tradeoffs between artistic freedom, platform growth, and audience expectations

Timestamped Chapters:

[00:00] Writing Without Talking About It
[01:00] Why Book Ideas Need Time in the Dark
[02:00] Creative Compulsion vs. Discipline
[03:00] Stand-Up, Dopamine, and Daily Feedback
[05:00] Point of View in a Binary World
[06:00] Silence, Ethics, and Speaking Up
[07:00] Noise as a Form of Violence
[09:00] Political vs. Philosophical Disagreements
[10:00] Social Media’s Shift to Opinion Farming
[11:00] The Algorithm as Audience Puppet Master
[12:00] When the Audience Has You
[13:00] Podcasting’s Algorithm Problem
[14:00] Are Podcasts Dangerous?
[16:00] Podcasting vs. Books: Tension and Craft
[18:00] The Rise of the Longform Grifter
[20:00] RFK Jr., Bad Ideas, and No Fact Checks
[22:00] Why Audiobooks Outperform Podcasts
[23:00] Can the Medium Save Us?
[25:00] When Podcasts Work (And When They Don’t)
[27:00] Music and the Emotional Power of Simplicity
[29:00] Songs vs. Culture War Commentary
[30:00] Great Lyrics, Great Feelings
[32:00] Bono, Stoicism, and Making You Feel Seen
[34:00] The Parasocial Magic of Fame
[35:00] Acting, Politics, and Emotional Truth
[37:00] Writing as the Hardest Artform
[39:00] Why Great Writing Still Matters

Additional Resources:

Ryan Holiday’s website: ryanholiday.net
The Daily Stoic by Ryan Holiday: Amazon
James Altucher on Twitter: @jaltucher
Ryan Holiday’s books on Amazon: Author Page
Olivia Rodrigo – “Drivers License” (YouTube): Watch here
Led Zeppelin lyrics and discography: ledzeppelin.com
U2 – “Sunday Bloody Sunday”: YouTube

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