Free Stoic Saturdays: Ideas from Ryan Holiday's Books

Ideas worth talking about, friends worth meeting.

Discover the practical wisdom of Stoicism in a fun, friendly, and informal setting! We’ll explore ideas from Ryan Holiday’s books, share experiences, and learn from each other—no need to have read everything.

This is a free gathering, open to anyone curious about Stoic thinking, personal growth, and thoughtful conversation. Come for the insights, stay for the community, and leave inspired.

Let’s explore how Stoicism can help us navigate modern life together—everyone is welcome!

| Book | Stoic Idea | Quotation | Discussion Question |
| ---- | ---------- | ------------------------ | ------------------- |
| 1. The Daily Stoic | Focus Only on What You Control | “The single most important practice in Stoic philosophy is differentiating between what we can change and what we can’t.” | When was the last time you spent a lot of energy on something outside your control? How might this principle have changed your response? |
| 2. Ego Is the Enemy | Ego Blocks Growth | “Impressing people is utterly different from being truly impressive.” | In what areas of life do you think ego gets in the way of learning or progress? |
| 3. The Obstacle Is the Way | The Obstacle Becomes the Path | “The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.” | What’s an obstacle you’re currently facing, and how might it be reframed as part of the path forward? |
| 4. The Obstacle Is the Way | How You Frame It Matters | “What matters most is not what these obstacles are; but how we see them, react to them, and whether we keep our composure.” | Do you think composure is more important than skill or talent in overcoming challenges? Why or why not? |
| 5. The Obstacle Is the Way | Failure Shows the Way Forward | “Failure shows us the way—by showing us what isn’t the way.” | How has a past failure helped guide you toward success or a better decision? |
| 6. Courage Is Calling | Courage Is a Choice | “You must decide: will you be brave? Will you step forward or back? Will you choose to see how much better you can be?” | Where in your life do you need more courage right now—taking action, speaking up, or making a change? |
| 7. The Obstacle Is the Way | True Willpower Is Quiet Strength | “True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition. See which lasts longer under the hardest of obstacles.” | Do you think resilience and humility are undervalued in modern culture compared to ambition and assertiveness? |
| 8. Stillness Is the Key | Stillness Is Power | “Stillness is the key to, well, just about everything.” | In today’s fast-paced world, what practices or habits help you slow down and cultivate stillness? |
| 9. Discipline Is Destiny | Discipline Creates Freedom | “Discipline is not a constraint. It is the route to real freedom.” | Do you agree that discipline can actually expand freedom instead of restricting it? Why or why not? |
| 10. Daily Stoic | Mind Is the True Kingdom | “According to the Stoics, the circle of control contains just one thing: YOUR MIND.” | How does the idea that your mind is the only thing you control change the way you think about freedom and responsibility? |