The best books on stoicism to live a virtuous life

I still remember the day my love for classical philosophy began (weird, I know!). It was my first semester as an engineering student in college and my schedule was packed with all of the expected courses: calculus, physics, chemistry, etc. But, I had room for one more class so I chose The Ancient World for two reasons: I heard the teacher was great and it had nothing to do with math or science!

Our first session was a whirlwind. I couldn't tell you exactly what we covered, but I left that day knowing I had found my thing. Fast-forward a few years, and I graduated with a Bachelor's in Classical and Medieval Studies.

If you're just getting started in the world of stoicism and ancient thought, the number of resources available can seem overwhelming. But don't worry, there are plenty of beginner-friendly, accessible titles that anyone can dive into. Below are my best recommendations, consisting of a mix of modern and classic titles, that are sure to get you thinking like the greats!

The Obstacle Is the Way

In every situation, life is asking us a question, and our actions are the answer. — Ryan Holiday

Modern stoicism owes a lot to Ryan Holiday. He's helped an entirely new generation discover the treasures of this ancient practice. But, he didn't begin by writing about these topics.

Ryan's early career was in marketing, and his first few books covered that area. It wasn't until later in life, after he had achieved a fair amount of success, that he began to distill the lessons that helped him get there.

This journey adds a depth to Holiday's interpretation that many other writers miss. Because he's lived out so many of the stoic principles, his writing on them stands shoulders above the rest. This book is by far the most entertaining and accessible introduction to stoicism.

The Little Book of Stoicism

What brings no benefit to the hive brings none to the bee. — Jonas Salzgeber

As someone who has spent a good portion of my life studying history, I love a good high-level overview. And that's exactly what readers get in this handy little guide.

Now, when talking about stoicism most people are referencing a collection of things: thinkers, ideas, and practices. For beginners, it can be easy to mix these up and misunderstand how one element influenced another. Grasping the order can be hugely beneficial when applying the concepts to your own life.

This short book is a perfect tool for that. The text is well-written and organized into short chapters so you can learn everything you need to by just reading a few minutes per day. I regularly use this as a quick reference guide.

Lives of the Stoics

Don’t explain your philosophy, embody it. — Epictetus

Before we get to a few of the original classics, I wanted to recommend one more book by Ryan Holiday. This title is essentially a combination of the two above: it brings Holiday's beautiful style and marries it with a reference-style book covering dozens of important figures.

This title is an advanced read since it spends more time covering the lives and stories of historical stoics than it does providing tactical lessons. However, what you'll likely find is that there are one or two characters you especially connect with and want to learn more about.

This is a great starting point to find their original works and become your own sort of niche-stoic expert.

Letters from a Stoic

Enjoy present pleasures in such a way as not to injure future ones. — Seneca

I'd be shunned as a classicist if I wrote an entire article about stoicism and didn't recommend an original work. Granted, these ancient books can be a little difficult to read — even after undergoing beautiful translations.

But if you could only read one, then it must be this Seneca masterpiece. Part philosophical treatise, part strategy guide, this book brings together the best stoicism has to offer.

If you have any difficulty understanding portions of the book, there are many excellent YouTube videos that offer solid insights such as this one.

The Practicing Stoic

We don’t react to events; we react to our judgments about them, and the judgments are up to us. — Ward Farnsworth

That last title I want to recommend to you fulfills its title exactly: a user's manual. Written by an award-winning professor of classics, this book distills centuries of thought into a step-by-step action plan.

Although stoicism is rich with practical insights, it can still be challenging to translate those into our modern world. What does judgment, wealth, and virtue look like in our contemporary setting? What should we take literally and which parts require a more nuanced view? How can we hold true to stoic ideals without falling into outdated, and even dangerous, rules?

Although I don't think this should be the very first book any stoic-enthusiast reads, it should absolutely be in your cart and on your shelf for when you're ready.

To read is to grow

Like so many of the most important things in life, the stoic philosophy must be approached slowly. Focus on learning and applying one lesson at a time. Be willing to make mistakes. And look for friends and partners who will hold you to the standard you are capable of. Because the world we want to create can only come as a result of maturing into the people we're meant to become.