It’s a good day to be a Geeky Stoics subscriber here on Substack! You all get first access to this week’s video conversations with Ryan Holiday of the Daily Stoic. I told you about the trip to Palm Springs, and it was to moderate this panel tackling the differences and overlaps of Stoicism and Objectivism.
To recap: Stoicism is ancient Greek and Roman philosophy rooted in self-mastery, emotional regulation, and letting go of things beyond your control.
Objectivism took form post-World War II through the philosopher and writer Ayn Rand. It is about self-focus, individual fulfillment, and “rational egoism” or putting yourself first as a matter of rational thought.
Ryan Holiday is famed for his books, "The Obstacle Is the Way," "Ego Is the Enemy," "The Daily Stoic," "Stillness Is the Key", “Courage Is Calling” and his new book “Wisdom Takes Work” comes out this fall. Millions of people receive his daily emails and podcasts, and most of what Geeky Stoics does would not exist without his work.
It was cool to meet him and ask him some questions about the life well-lived.
Some takeaways
Holiday framed freedom as the opportunity for self-discipline. Drawing on figures like Marcus Aurelius, Epictetus, and even Eisenhower, he emphasized that inner liberty (freedom from passion, chaos, and internal compulsion) is central to Stoic ethics. Stoicism holds that true freedom is achieved through mastery of the self, rather than simple absence of constraint.
In Ryan’s books, he has called this “the empire between your ears”. Even a person living in chains cannot be truly forced to vacate their freedom of thought and action.
For Stoics, unchecked liberty is a quick road to being enslaved by desire, and so self-restraint is not seen as a limitation but as a form of empowerment.
This is an area I tend to strongly agree on.
Richards, representing Ayn Rand’s Objectivism, defined freedom as freedom from coercion (force or fraud) that threatens one’s ability to think, act, and pursue personal happiness. Objectivism prioritizes the individual’s rational mind as the highest tool for flourishing, arguing that the pursuit of joy and personal achievement is the purpose of freedom. It’s not dismissive of self-discipline, and so Richards emphasized how a person can harm oneself with the pursuit of constant vice.
Enjoying the panel discussion? Now check out our 1-on-1 interview with Ryan Holiday about parenting, Hamilton, and philosophy
Overlap and Contrast on the panel
Both philosophies value rationality, personal responsibility, and civic virtue. However, Stoicism is inward-facing, concerned with moral resilience and inner peace, while Objectivism is outward-facing, focused on creative achievement and individual flourishing.
Holiday illustrated Stoic freedom with the example of Epictetus—a slave who, despite literal bondage, enjoyed greater internal freedom than Rome’s elite who had to suck up to tyrants to make a living. Richards acknowledged this but argued that Objectivism’s strength lies in its systematic approach, beginning with metaphysics and epistemology, and ending in ethics and politics centered on the primacy of the individual. It’s very anti-collectivist.
That point on collectivism is important because it’s perhaps the most pointed area of disagreement.
Most Stoics would say that all “goods” must be considered for the whole of a community. Objectivists, or Ayn Rand, did not believe “the public” even exists. Her philosophical focus was on living, breathing things, and she rejected the notion that the disjointed “we” was a thing worthy of acknowledgement.
I am alive. The “public” is not. I have interests. The public does not.
Stoics don’t buy this, especially not Ryan Holiday.
Now, go enjoy the discussion and tell us what you thought in the comments below.
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