Ryan Holiday has introduced millions of people to Stoicism. But is what he teaches about success actually consistent with what the ancient Stoics taught?

In this episode, I take a closer look at several of Holiday’s claims about success—not to tear him down, but to test those ideas against the philosophy itself.

We explore why Stoic success cannot be measured purely by outcomes, what the Stoics actually meant by preferred indifferents, why making more money isn’t necessarily the Stoic choice, and a revealing passage from Seneca’s Letter 95that raises a larger problem with the way Stoicism is sometimes presented today.

Because Stoicism isn’t fundamentally about becoming more effective at getting what you want.

It asks a much harder question:

Is what you want actually worth wanting?

Ryan Holiday gets some things right. Other ideas, I argue, are incomplete. And in at least one case, returning to the original Stoic text tells a very different story.

A successful life and a good life are not necessarily the same thing.

The Stoics were concerned with the latter.

If someone could hear your thoughts for a week, who would they expect you to become?

Marcus Aurelius wrote that “the soul becomes dyed with the color of its thoughts.” But not every thought stains us. An unwanted impulse is not character. The danger lies in the thoughts we repeatedly entertain, rehearse, defend, and eventually act upon.

In Episode 429, Brandon explores how thoughts become words, words become actions, actions become habits, and habits become character. He examines why our speech reveals what the mind has been soaking in, how our closest relationships influence our inner lives, and where we can intervene before a passing impression becomes a permanent way of seeing the world.

You cannot always control the first thought that enters your mind. You can decide whether to give it a room, a voice, and a place in your future.

In this episode:

• Why Marcus Aurelius emphasized habitual thoughts
• The difference between an impulse and a rehearsed judgment
• How thoughts become character one small decision at a time
• Why your speech reveals the “color of the dye”
• How gossip, resentment, and excuses train the mind
• The influence of your environment and closest friends
• How to interrupt a destructive thought before it becomes destiny

David Goggins believes in scheduled suffering, rejecting motivation and refusing to stop before the work is done. His philosophy has helped millions confront comfort, excuses and unrealized potential.

But is Goggins actually a Stoic—and when does relentless discipline become self-punishment?

In this episode, Brandon examines eight of Goggins’ central ideas through a Stoic lens, including the 40% Rule, voluntary discomfort, accepting help, recovery, permanent change and the difficult decision to quit something meaningful.

Goggins gets several things profoundly right: motivation is unreliable, confidence must be earned, and a comfortable life can quietly become a smaller life. The danger appears when pain becomes an identity, recovery feels like weakness, or self-contempt begins masquerading as discipline.

The Stoic correction is neither softness nor relentless punishment. It is deliberate hardship governed by wisdom.

Chosen hardship becomes strength when it serves a worthy purpose. It becomes self-punishment when suffering itself becomes the purpose.

The Strong Stoic Notebook is available here: Strongstoic.substack.com

Living intentionally does not mean avoiding regret. It means deciding which regrets you are willing to carry.

In this episode, Brandon is joined by Joshua Bertolotti for an honest conversation about busyness, rest, vulnerability and the difficult work of examining your own life. They discuss why we often plan ordinary tasks more carefully than our futures, how constant activity can conceal exhaustion, and why slowing down is sometimes the most responsible thing we can do.

The conversation also explores emotional honesty, the relationship between vulnerability and toughness, and the courage required to acknowledge when we are struggling.

Every meaningful path demands a sacrifice. The question is whether you are choosing yours—or simply accepting the one life gives you.

This episode includes sensitive emotional and mental-health-related themes.

Why do certain insults stay with us while others have no effect at all?

In this episode of The Strong Stoic Podcast, I examine what our emotional reactions reveal about us—and how to respond to difficult people without becoming passive, cruel, or emotionally numb.

Sometimes anger exposes an insecurity. Sometimes contempt points toward a version of ourselves we fear becoming. Sometimes we suffer because we decided another person owed us respect, recognition, affection, or fairness.

The Stoic response is not to pretend that pain is unreal. It is to examine the judgment, take responsibility for what remains within our control, and refuse to let another person’s lack of character determine our own.

In this episode:

• Why the same words affect people differently
• The danger of using self-hatred as motivation
• How ego turns harmless comments into personal attacks
• Why acceptance does not mean approval
• When walking away is an act of discipline
• How compassion and boundaries can coexist
• Why physical health affects emotional control
• What Stoicism actually teaches about emotions

The goal is not to feel nothing. The goal is to handle what you feel without surrendering your character.

If this episode helped you, share it with someone who might need it.

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Resentment often begins where an important boundary remains unspoken.

In Episode 425, we examine why boundaries exist in every healthy relationship—and why setting one is not necessarily an act of rejection. A clear boundary tells another person what matters, what you are willing to participate in, and what you will do if the line is crossed.

We also explore the difference between boundaries and preferences, the discomfort of receiving someone else’s boundary, and the danger of becoming so rigid that healthy limits turn into walls.

The goal isn’t to create relationships where boundaries are never crossed. The goal is to communicate clearly, follow through without cruelty, and leave a path back when repair is possible.

Boundaries cannot control another person. They can only govern how you choose to respond.

Have you ever stopped enjoying something that once gave your life meaning?

Maybe it's the guitar that now gathers dust. The running shoes that haven't left the closet. The books you used to devour but can't seem to pick up anymore.

In this episode, I explore why our interests naturally change throughout life, why there's nothing wrong with losing a passion, and what Stoicism has to teach us about work, play, gratitude, and non-attachment.

Sometimes the healthiest thing we can do isn't force ourselves back into an old hobby—it's to let it go, trust the season we're in, and welcome it back if life ever calls us there again.

We discuss:

• Why we don't choose what fascinates us
• The difference between work and play
• Why joy is deeply Stoic
• Letting go without losing yourself
• Following curiosity instead of obligation
• Why gratitude is wiser than possession

Have you ever looked in the mirror and realized you’ve become someone you don’t respect?

I have.

In this deeply personal episode, I share a chapter of my life I’ve rarely talked about—the years after university when I slowly drifted into complacency. What began as well-earned rest became laziness, comfort, and eventually shame. One day I looked at the man I was becoming… and I didn’t like him.

This episode is about the long, humbling process of rebuilding your character.

We explore:

• Why good people can slowly become complacent
• How your environment quietly shapes your character
• The danger of becoming comfortable with mediocrity
• Why you must start much smaller than you think
• The Stoic idea that character is built through daily choices, not grand moments

If you’ve been feeling stuck, unmotivated, or disappointed in who you’ve become, this episode is a reminder that your story isn’t over.

You don’t have to become a different person overnight.

You just have to take the first small step.