Lessons on Stoicism with Ryan Holiday

The Boy Who Would Be King (children's book)

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Hi curious minds 🧠,

Fireside chat #2 with Ryan Holiday! (watch our first chat)

We dive into Stoicism through the lens of his first children’s book The Boy Who Would Be King, the incredible story of Rome’s Emperor, Marcus Aurelius.

Watch our chat below and read on for my favorite lessons.

Chat also available on The Daily Stoic podcast.


Meet Ryan Holiday.

Guest: Ryan Holiday is the founder of Daily Stoic and New York Times bestselling author of Stillness Is the KeyEgo Is the Enemy, and The Obstacle Is the Way.

What is Stoicism? Stoicism was founded in Athens by Zeno of Citium in the early 3rd century BC, and was practiced by Epictetus, Cato, Seneca, and Marcus Aurelius. The philosophy asserts that virtue (such as wisdom) is happiness and judgment be based on behavior, rather than words. That we don’t control and cannot rely on external events, only ourselves and our responses.

(click the image below to watch on Facebook or click this link).

Lessons on Stoicism.

Lesson #1: Stoicism is built around four virtues: Courage, Discipline, Justice, Wisdom. No one is fit to rule who hasn’t first mastered themselves.

“Fight to be the person philosophy tried to make you.” — Marcus Aurelius

Lesson #2: To teach your kids Stoicism, Ryan recommends to (a) embody it and (b) focus on individual lessons, reinforcing the Stoic principle that we do not control what happens, but we control how we respond, in everyday life (e.g. when a kid breaks their arm, gets cut from the soccer team).

“Don't talk about your philosophy, embody it.” — Epictetus

Lesson #3: Marcus Aurelius’ teacher (Rusticus) said “Nothing should encourage us as much as the different qualities of the people around us.” Actively work to disconfirm your beliefs and seek different perspectives. Ryan recounts how Marcus Aurelius decided to see first-hand the kingdom he was supposed to lead. He walked the streets to meet hungry beggars, desperate gladiators, scheming senators, aggressive merchants, and where the rich lived well and the poor suffered.

“It's impossible to learn that which you think you already know.” — Epictetus

Lesson #4: Develop a love for learning. Ryan introduces his kids to big ideas and people they can learn from and ask questions to (vs. memorizing facts). Actively seek mentors and catalog what you learn. In Meditations, Marcus Aurelius thanks his various teachers (e.g. rhetoric, philosophy, Latin, grandfather, adopted father, etc.).

Lesson #5: Rusticus said “Through the pages of a book, we can talk to people who lived long ago, and learn easily what they learned with great difficulty.” Ryan views reading as part and parcel of becoming great at whatever you choose to do in life - the younger you start the better. Push yourself to read something you do not understand now, then come back to it five years later.

Other books Ryan mentioned:
(a) The Little Prince,
(b) The Boy, the Mole, the Fox and the Horse,
(c) Poem For Every Night Of The Year,
(d) Way of the Warrior Kid: From Wimpy to Warrior the Navy SEAL Way: A Novel.

“Not all readers are leaders, but all leaders are readers.” — Harry Truman

Lesson #6: There is a perception that Stoicism is a resignation — however, almost all Stoics were active participants politically, socially, and in their careers and communities. Stoicism is actively trying to make the world better while accepting that many things are outside of our control. A Stoic tries to root their ambition solely in things that are up to them.

“If, at some point in your life, you should come across anything better than justice, wisdom, discipline, courage—it must be an extraordinary thing indeed.” — Marcus Aurelius

Keep reading. Keep learning. Thanks for the peculiar chat Ryan!

Listen via The Daily Stoic Podcast.


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