Getting started with Stoicism in 2021

Here’s my take on where to start with Stoicism. I’ve attempted to put the books into some kind of order for you. This is how I would approach it if I started over. Of course, I haven’t read all the books that exist on the subject (probably impossible…!), and so I can only recommend what I’ve already read.

Starting with Ryan Holiday is a good idea – The Obstacle is the WayEgo is the Enemy and Stillness is the Key.

These are all great introductions to key concepts from the Stoics.

Ryan does a great job of curating Stoic lessons around these major themes – Dealing with challenges, dealing with our ego, and why finding stillness is critical in the modern day. The Obstacle is the Way is where it all started for me.

The fundamentals of Stoicism

While you are reading these books it would be worth noting the areas of your own character that you’d like to work on. Where would you like to be better? What situations would like to respond better to? What don’t you like about your own character? What are your values?

  1. A guide to the good life by William Irvine – This is a really great place for getting to grips with the major building blocks of Stoicism. Irvine walks through all the major principles/disciplines of Stoicism and will provide you with a broad overview.
  2. Lessons in Stoicism by John Sellars – This is a tiny little book (<70 pages) that summarises the major principles of Stoicism. This is a great little introduction to Stoicism.
  3. How to be a Stoic by Massimo Pigliucci – I really enjoyed reading this book. Pigliucci uses Epictetus as his guide to teach us about what it means to be a Stoic. You’ll see the follow up to this book in the next section. In chapter 14 there’s a list of 12 spiritual practical exercises you can try out. 

The practice of Stoicism

Stoicism is a practice. You’ll learn a lot from the books, but, in my experience, you’ll learn a lot more when you read and write a little everyday and start to put the principles into practice as challenges crop up in your day to day life.

These books are a great place to start:

  1. Daily Stoic Journal by Ryan Holiday – There are two complimentary books – The Daily Stoic has the daily passages, and The Daily Stoic Journal is the one you write in that has the daily prompts. You will use both books each day as you set yourself up for the day and reflect on the day. It’s all about continual improvement and being a little better each day. 
  2. Live like a Stoic by Massimo Pigliucci – I love this book. It’s super practical with 52 guided exercises for integrating it into your daily practice. In his book I listed in the first section above, he briefly mentions the link between Stoicism and modern day cognitive therapy, and this is when you will see that link directly in the practice of living like a stoic. 

The three Stoics

There are three major Stoics that make up the majority of the Stoic doctrine (there are many more, but these are the most popular and most referenced and revered today…in fact, Ryan Holiday’s new book, Lives of the Stoics covers many more ancient philosophers and the founders of Stoicism)

  1. Marcus AureliusMeditations is his own private notes and all that has survived of his journals. The Gregory Hays translation is often referenced as the best translation, although there are others.
  2. Epictetus: There are two popular publications to read – Enchiridion (Handbook) and Discourses.
  3. Seneca: Out of these three main characters Seneca has written the most and is the most widely read, so there are many publications from Seneca, and the place to start is with Letters from a Stoic(This is by far my favourite)

The study of Stoicism

Honestly, there’s just a lifetime of reading and study you can do, and with this being a ‘getting started’ guide, here are another two books I enjoyed that go a little bit further:

  1. How to think like a roman emperor by Donald Robertson – I really enjoyed this book because it’s written by a modern day psychotherapist and it makes the case for link between the Stoicism and the foundations of Cognitive Behavioural Therapy (CBT). This book made me even more dedicated to Stoicism, and also heightened my interest in CBT.
  2. The Inner Citadel by Pierre Hadot – This is a deep dive into the life of Marcus Aurelius and an attempt to add more context to Meditations so we can understand better what Marcus may have been thinking or going through when he was writing in his private journal. Probably best to read Meditations first, and if you like it, then you’d probably feel inclined to read this to grasp the history.

Other Stoic resources

Here’s a quick list of other places you will get al lot of value from…

I’m aware that it’s heavy on the ‘Ryan Holiday’, and that’s not only because I see him as my ‘guide’ through Stoicism, but he’s arguably the best curator of our time. I like his work, hopefully you do too…🙂

Oh, and there’s also a really cool collection of books that you will come across in books stores, keep an eye out for them and pick up the ones you like – Ancient Wisdom for Modern Readers by Princeton University Press.

I hope this helps you on your Stoic journey 🙂


Note: All links to books on this page will take you to AMAZON UK. Once you know what books you’d like to buy, I encourage you to buy them from an independent book store 🙂