
I can’t remember what prompted me to delve deeper into Stoicism; I was maybe a few days into researching the subject matter when I saw Ryan Holiday tweeting about his course Stoicism 101 and decided to sign up for it.
If you don’t know who Ryan Holiday is, let me give you a brief introduction. Ryan Holiday is a writer and media strategist who has been learning and practicing Stoicism for more than ten years. He has authored books based on Stoic philosophy, with some of his popular books being The Obstacle is the Way, Ego is the Enemy, The Daily Stoic, and Stillness is the Key.
About the Stoicism 101 Course: Ancient Philosophy for Your Actual Life

I would say that Stoicism 101 Course: Ancient Philosophy for Your Actual Life is perfect for beginners like myself who are just dipping into the subject.
Ryan did mention to the course participants that we should approach the course “with a beginner’s mind. If you are familiar, it’s to reset foundations.” So I suppose those who have practiced Stoicism for a while can also take this course to revisit the basics.
As a course participant, I received an email a day for about two weeks. The email covers the basic history and concepts of Stoicism. The course also offers 5 Office Hours sessions with Ryan Holiday himself, where participants can ask questions.
Unfortunately for me, the live Office Hours sessions were scheduled at 3 am Malaysian time, so I could not join in the session. However, recordings of the Office Hours sessions were shared with course members for review at our own convenience.
In addition to the daily emails and Office Hours sessions, there is a Slack community channel that we can access and connect with other course members to ask questions, share or discuss ideas on Stoicism. I have been on the channel a few times but have yet to connect with anyone.
Overall I thought the course was great. Ryan Holiday’s emails were short and succinct. The emails were interesting and engaging. He tells compelling stories to bring his message across clearly. Ryan is an exceptional storyteller, and I looked forward to reading the emails daily.
The course covered the basics of Stoicism, its history, the Stoics themselves, such as Marcus Aurelius, Seneca, Epictetus, and the Stoic virtues and practices, and how we can use them in our life in the modern world.
What I thought was valuable other than the Office Hours sessions with Ryan himself was the recommended list of books that he had outlined for those who want to learn more about Stoic philosophy.
Note: At the time of writing this, I noticed that the Stoicism 101 course is offered at a discounted price but without the Office Hours or access to the Slack Community Channel.
What I learned from Ryan Holiday’s Stoicism 101 Course- A Summary
Stoicism is for Everyone
Stoicism can be practised by anyone interested in self-improvement. Philosophers are everyday people who face everyday problems just like us.
As the philosopher and mathematician Blaise Pascal explained, writing some five hundred years ago, “We always picture Plato and Aristotle wearing long academic gowns, but they were ordinary decent people like everyone else, who enjoyed a laugh with their friends.” Pascal took pains to point out that the books they wrote were written for pleasure and enjoyment—they were not stuffy, pretentious documents meant to intimidate people.”
Philosophy is not something you study; it is something you practice. Philosophers are people who seek to live better lives and creating a better version of themselves, intellectually, morally, and spiritually through knowledge and implementation of that knowledge.
You Don’t Have to be Emotionless to Practise Stoicism
Practicing Stoicism doesn’t mean that you need to be stoic. A Stoic is not emotionless, does not seek to eliminate emotions but rather to regulate them. A Stoic has strong self-awareness and knows how to use their emotions, and is in control.
Ryan quoted Nassim Taleb, who has said, “A Stoic is a vibrant, action-oriented, feeling human being who is interested in being a better person and living a better life. Stoicism “is not about turning humans into vegetables,” “My idea of the modern stoic sage is someone who transforms fear into prudence, pain into information, mistakes into initiation, and desire into undertaking.”
“Philosophy Offers Counsel” – Seneca
Our problems are not new. The context in terms of time may be different, but humans have struggled with the same problems; relationships, dealing with others, health, wellness.
Stoicism was designed to help people live life the best way possible, and all we need to do is use their wisdom, principles, and values that have existed for thousands of years as a guide on how we can be better versions of ourselves.
What Next?
As someone committed to self-betterment, I found that I was already practicing some of the Stoic principles. The practice of Stoicism is definitely something that I’d like to dive into further and learn more about. While I am interested in pursuing a deeper understanding of the topic, I would still like to explore philosophers other than the Stoics.
My next step would be to better understand Stoicism by reading some of the books recommended by Ryan.
Ryan had provided a long list of book recommendations but I’m looking to start reading these first: