So you're ready to start reading about Stoicism? You're in the right place. Below I have put together a reading list that should offer you more than enough Stoic inspiration. I'll start with the essentials (if you haven't ready anything about Stoicism then you should start with these books and then move to the rest), and then I'll give you some other ideas for where you can go from there.
LETTERS FROM A STOIC by Seneca the Younger
I am completely biased towards this book because it was the first book on Stoicism that I ever read, but I don't think that I'm wrong to put it at the top of the reading list.
Seneca was a wealthy investor, play write, advisor to Nero, politician, and orator, and this book is basically a collection of letters that he wrote to his friend, Lucilius, about life, morality, friendship, courage, desires, nature, health, finances, and many other topics. Because they are so intimate, only meant for two friends, it can often seem like Seneca is writing to you.
Every single page contains advice that could change your life, and every time I go back and re-read it I find myself highlighting more (it's almost at the stage where there are no un-highlited sentences).
MEDITATIONS by Marcus Aurelius
This book is an absolute game changer. Marcus Aurelius was one of the five good emperors of the Roman Empire, and Meditations is a collection of his own personal journal entries.
What makes this book so special is the fact that he never intended for these writings to be published. They were for him, and for him only. His thoughts are personal and extremely thought-provoking, and for anyone who truly wants to get into the mind of one of the greatest Stoics who ever lived, then this is your book.
DISCOURSES AND SELECTED WRITINGS by Epictetus
Epictetus spent much of his life as a slave, and yet when he was freed he spent the remainder of his life living in humble means and teaching people how to live a beautiful life.
This book is a collection of Epictetus' teachings that were written down by one of his students. These writings really are an endless source of Stoic inspiration, and there is so much practical advice for how to live a better, and more effective life.
This is an absolute must-read for anyone who wants to align their life more closely with Stoicism.
LECTURES AND SAYINGS by Musonius Rufus
Musonius Rufus was one of the lesser-known Stoics, however his contributions to Stoicism cannot be overstated.
This book is less of an "essential" than the previous three, however it is a natural progression seeing as Rufus was the philosopher who taught Epictetus about Stoicism.
These writings will definitely give you some added background to the teachings of Epictetus and Marcus Aurelius, and they will inspire you in many areas of your life.
ON THE SHORTNESS OF LIFE by Seneca the Younger
This is another incredible collection of letters from Seneca, but with a particular focus on the shortness of life.
If you've ever wished that you could live longer, or felt as though you didn't have enough time to live the life that you want, then this is your book. Seneca will smash you.
The basic idea is that we all have enough time to live how we want to live. The happy life is not dependent on length but depth, or in other words, it doesn't matter how long your life is; what matters is how good it was.
THE ART OF LIVING by Epictetus (Modern Translation by Sharon Lebell)
This was the first book that I read from Epictetus, and it was a really amazing place to start.
Sharon Lebell does a great job of taking some of the core teachings of Epictetus and breaking them down into bite-sized pieces.
It is a great book for anyone who wants to get immediate access to life-changing advice, because you can literally turn to any page and you'll find practical and actionable Stoic teachings.
ON THE HAPPY LIFE by Seneca the Younger
Yet another collection of beautiful letters from Seneca.
This is a very quick read, but it is packed full of incredible advice for how to life an amazing life.
THE NEXT STEP
If you're done with the classics and you still want more, then here is a list of books that I currently have on my shelf that have also been a source of Stoic inspiration to me. I should also note that a few of these books (like "Man's Search for Meaning", and books by Henry David Thoreau) may not be directly related to Stoicism, however because of their "Stoic nature" if you read them after having read the classics then they will strengthen your Stoic values and help you to live a life more closely aligned with Stoicism.