Want to Learn About Stoicism? Read These 7 Books (in Order)
A bit of modern reading, mixed with some of the all-time classics
Glasp’s note: At Glasp, we value the close personal relationships we’ve built with thinkers, creators, and doers who fuel curiosity and growth. This week, we spotlight Bobby Powers —a lifelong learner passionate about leadership development and continuous improvement. With more than a decade of experience leading teams and developing learning and development at startups, Bobby understands the transformative power of curiosity and mentorship. You might remember him from his Glasp Talk appearance, where he shared insights on leadership and personal growth, inspiring thousands. We’re honored to continue learning from Bobby and are thrilled to share his thoughtful reflections with our community.
If you want to reread or highlight this newsletter, save it to Glasp.
I’m Bobby Powers, and I run the Leader & Learner publication, where I write two posts per week that will help you become a more curious leader and learner.
For the past decade, I’ve been reading at least 70 books per year (mostly nonfiction), and I’ve gotten to share what I’m learning with over 1 million readers online.
One of the most impactful concepts I’ve learned from my reading is the philosophy of Stoicism. I now view it as one of the core operating systems of my life, and you’ll begin to see why in this post.
What Is Stoicism?
The school of Stoic philosophy was founded in Greece by Zeno around 300 B.C. It’s centered around four cardinal virtues (wisdom, temperance, justice, and courage), and one of the core tenets of Stoic thought is to differentiate between what you can and can’t control in life, then focus entirely on the former.
Stoicism has guided titans of history ever since, including George Washington, Montaigne, Adam Smith, Mary Wollstonecraft, and Teddy Roosevelt.
But its prominence surged recently due to authors like Ryan Holiday and proponents like Tim Ferriss, Arianna Huffington, and General James Mattis.
“Stoicism is a fantastic operating system for thriving in high-stress environments.” -Tim Ferriss
I’ve been reading about Stoicism for the past 10 years. I’ve read the foundational texts as well as modern-day ones, so friends often ask me for recommendations to learn more about this ancient school of philosophy that has helped millions of people.
If you’ve heard people mention Stoicism but you’ve always wondered what it’s all about, this list will help you get started. I’ve structured these seven books in order of when I think you should read each book, based on approachability, length, and impact.
Book #1 — The Obstacle Is the Way by Ryan Holiday
When It Was Written: 2014
Why You Should Read It: The Obstacle Is the Way is the best gateway drug to Stoicism. It’s a lean 200 pages, and Holiday’s writing is full of stories and pithy quotes. Plus, this book kicked off the modern-day Stoic movement. After it was published, several prominent sports teams like the Seattle Seahawks and New England Patriots said the book had a huge impact on their success, which prompted tons more people to read it.
What to Expect: Lots of short chapters full of anecdotes from throughout history (including business, art, and athletics)
The Biggest Lesson I Learned: One of the most important life lessons anyone can learn is to focus on what you can control and not worry about what you can’t. That concept lives at the core of Stoicism, and it’s a useful mindset for approaching any challenge. As a few examples of what we can and can’t control:
Controllable: Work ethic, preparation, mentality, how you rebound after failure
Uncontrollable: Others’ actions, emotions, opinions, etc.
Two Passages I Loved:
“It’s not just: How can I think this is not so bad? No, it is how to will yourself to see that this must be good—an opportunity to gain a new foothold, move forward, or go in a better direction. Not ‘be positive’ but learn to be ceaselessly creative and opportunistic.
Not: This is not so bad.
But: I can make this good.”
-Ryan Holiday
“Just because the conditions aren’t exactly to your liking, or you don’t feel ready yet, doesn’t mean you get a pass. If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started.” -Ryan Holiday
Book #2 — The Practicing Stoic by Ward Farnsworth
When It Was Written: 2018
Why You Should Read It: The Practicing Stoic is a fantastic overview of Stoic thought. In this philosophical primer, law professor and former dean Ward Farnsworth provides a smattering of quotes and insights from Stoics throughout history.
What to Expect: Every chapter explains how the Stoics approach a different topic, like death, wealth, emotion, adversity, etc. Farnsworth briefly frames each topic, then the rest of each chapter contains passages from Stoic thinkers. He includes insights from the “Big Three” in Stoicism (Seneca, Epictetus, and Marcus Aurelius) as well as other more modern Stoics (Samuel Johnson, Montaigne, Schopenhauer, Emerson, etc.)
The Biggest Lesson I Learned: When we are upset, we have no one to blame but ourselves. I’m in charge of my own emotions, and you’re in charge of yours. If you wrong me, I get to decide how to respond. I can choose whether or not I want to feel “harmed” by what you did.
Two Passages I Loved:
“Nothing is heavy if we take it lightly; nothing need provoke anger if one does not add one’s anger to it.” -Seneca
“There is no difference, so far as contentment is concerned, between having something and not caring whether you have it. The second route is often easier.”
-Ward Farnsworth
Book #3 — On the Shortness of Life by Seneca
*Note: I read the translation by C. D. N. Costa, which was excellent. That’s also the translation recommended by Ryan Holiday and his team at The Daily Stoic.
When It Was Written: Roughly AD 49
Why You Should Read It: In terms of insights per page, On the Shortness of Life may be the best ROI you’ll ever get. It’s a slim 100 pages, and it reframed the way I think about life, death, productivity, prosperity, and mental health. Seneca’s1 other books like Letters from a Stoic are also amazing, but much longer and denser. Start here, get your feet wet, then dive into the deep end with some of Seneca’s other work.
What to Expect: On the Shortness of Life is chock full of quotes that could keep your Twitter or Instagram account buzzing for days. (Btw, here’s a long list of my favorite quotes from the book.) Seneca is one of history’s deepest thinkers, and he’ll prompt you to consider what you’re doing with your life.
The Biggest Lesson I Learned: It helped me re-evaluate where I’m spending my time and what I’m allowing into my head. Am I focused on the right things? How much time am I spending on what’s most important to me? Am I allowing myself to get anxious about things that don’t matter?
Two Passages I Loved:
“It is not that we have a short time to live, but that we waste a lot of it. Life is long enough, and a sufficiently generous amount has been given to us for the highest achievements if it were all well invested.” -Seneca
“I imagine many people could have achieved wisdom if they had not imagined they had already achieved it.” -Seneca
Book #4 — Meditations by Marcus Aurelius
*Note: Get the translation by Gregory Hays. In ancient books like this, translations can be the difference between a book that’s easy to understand and one you don’t want to finish.
When It Was Written: Roughly AD 161-180
Why You Should Read It: Marcus Aurelius kept a journal when he was the Roman Emperor. It’s not often we get to take a peek into the pages of a powerful person’s diary, and that’s exactly what this is. He didn’t intend for it to be published, and it’s a fascinating look into the types of things he reminded himself every day.
What to Expect: Even though this book was written 2,000 years ago, it reads easily. I enjoyed it enough that I’ve already read it a couple of times, and I’ll continue to revisit it throughout my life. Meditations is full of little things Marcus was trying to improve in his mental life: equanimity, work ethic, perseverance, etc.
The Biggest Lesson I Learned: Marcus realized that humans are inherently lazy, so he did everything in his power to notice negative traits in himself and work to overcome them. If one of the most powerful men in history had to remind himself of little mantras and principles, I need to do the same.
Two Passages I Loved:
“Our life is dyed by the color of our thoughts.” -Marcus Aurelius
“Be tolerant with others and strict with yourself.” -Marcus Aurelius
Book #5 — The Art of Living by Epictetus (A new interpretation by Sharon Lebell)
When It Was Written: 1994, based on Epictetus’s work from roughly AD 125
Why You Should Read It: The Art of Living is another 100-page book that punches way above its weight class. If you’re not sure you want to dive fully into Epictetus’s larger work yet2, this is a great stepping stone.
What to Expect: Short chapters full of memorable wisdom. This is a modern interpretation that’s largely pulled from Epictetus’s The Enchiridion. It’s not a direct translation. Lebell took Epictetus’s insights and shaped them into a powerful and eminently readable little book.
The Biggest Lesson I Learned: There’s a difference between what happened and your interpretation of what happened. All events are neutral, even things like losing a job or breaking an arm. We get to determine how we respond to that neutral event, and that response can lead to either positive or negative outcomes in our lives. (Shockingly, I’ve found this to be true in my own life, such as losing a job only to later find a better one.)
Two Passages I Loved:
“When something happens, the only thing in your power is your attitude toward it; you can either accept it or resent it. What really frightens and dismays us is not external events themselves, but the way in which we think about them. It is not things that disturb us, but our interpretation of their significance.” -Epictetus (interpreted by Sharon Lebell)
“It is always our choice whether or not we wish to pay the price for life’s rewards.”
-Epictetus (interpreted by Sharon Lebell)
Book #6 — Discourses by Epictetus
When It Was Written: Roughly AD 108
Why You Should Read It: Discourses is the main surviving work of Epictetus (and the version I’ve linked here also contains his smaller manual The Enchiridion). Epictetus’s life proves that Stoicism can be used by anyone in any situation. Unlike others on this list like Marcus Aurelius and Seneca, Epictetus wasn’t rich and powerful. He was born into slavery and—even after he was freed—lived a life of simplicity.
What to Expect: The book is laid out in a series of numbered passages, and each contains a short lesson. It’s slightly harder to read than Meditations, but still quite approachable considering it was written shortly after Jesus walked the Earth.
The Biggest Lesson I Learned: Not only is every event neutral, but it’s possible to benefit (at least in a small way) from anything that happens in life. Epictetus says, “Everything, you see, that you throw at me I will transform into a blessing, a boon—something dignified, even enviable.” Even though they can really suck, challenges develop us into stronger people.
Two Passages I Loved:
“So is it possible to benefit from these circumstances? Yes, from every circumstance, even abuse and slander. A boxer derives the greatest advantage from his sparring partner—and my accuser is my sparring partner. He trains me in patience, civility and even temper.” -Epictetus
“We forever compound our problems and make our situations out to be worse than they actually are. So, for instance, whenever I’m on board ship and gaze into the deep, or look around me and see nothing but ocean, I’m gripped by terror, imagining that if we wreck I will have to swallow all this sea. It doesn’t occur to me that around three pints will about do me in. So is it the sea that terrifies me? No, it is my imagination.” -Epictetus
Book #7 — Letters from a Stoic by Seneca
When It Was Written: Roughly AD 63-65
Why You Should Read It: Letters from a Stoic is one of the three foundational texts of Stoicism, and it’s packed with insights on how to live a better life. The book is written as a series of letters from Seneca to his friend Lucilius, talking him through how to approach various problems in life.
What to Expect: This is the densest book on the list. I loved it and learned countless insights, but it was still a tough book to finish because it’s long and meaty, which is why I put it last on this list. It’s definitely worth your time, but work your way up to it.
The Biggest Lesson I Learned: Don’t allow the future to torture you. We can’t control the future (or the past), so the better part of wisdom is learning how to live 100 percent in the present. That’s easy to say and difficult to do. It requires mental exercise, which Seneca details in this book.
Two Passages I Loved:
“The present alone can make no man wretched.” -Seneca
“As long as you live, keep learning how to live.” -Seneca
One Final Note
There are three foundational books of Stoicism:
I included all three above, but I’ve also included more recent books because I’ve noticed that some people are apprehensive of diving straight into a 2,000-year-old book of philosophy. Plus, the newer books do a good job of building on this old school of Stoic wisdom.
None of the foundational books is as crazy difficult as David Foster Wallace or James Joyce. They’re all fairly approachable. However, many readers may enjoy dipping their toes in the water by first reading the books I’ve outlined above.
I hope you enjoy these great books. Each one includes an affiliate link from Bookshop.org. (If you buy one, you’ll support me as well as local bookstores. Win-win!)
If you’re interested in receiving two posts per week with book recs and personal development tips, I’d be honored for you to subscribe to Leader & Learner.
📣 Community Updates by Glasp
🟥 Glasp Talk with Bobby Powers:
Glasp Talk features intimate interviews with luminaries, revealing their emotions, experiences, and stories. The guest, Bobby Powers, is a dedicated learner passionate about leadership and personal development. With over a decade of experience managing teams, leading onboarding, and Learning and Development programs at various startups and SMBs, Bobby is also an avid reader, having read over a thousand books in the last 15 years.
✨ Want a concise summary before diving in? Install the YouTube Summary with ChatGPT extension by Glasp for instant video summaries!
Would you like to take Glasp on the go?
With the Glasp mobile app, you can highlight and organize your favorite content anytime, anywhere. Stay productive on the move and never miss an insightful quote.
Partner With Glasp
We currently offer newsletter sponsorships. If you have a product, event, or service you’d like to share with our community of learning enthusiasts, sponsor an edition of our newsletter to reach engaged readers.
Share Glasp Newsletter
You may have heard of two different men named Seneca: “Seneca the Elder” and “Seneca the Younger.” Whenever you hear of “Seneca” regarding Stoicism, it’s Seneca the Younger (otherwise known as Lucius Annaeus Seneca). That confused me a bit when I first got into Stoicism, so I figured I’d mention it here.
Technically, Epictetus didn’t write any books himself. Any surviving work that bears his name was recorded by his loyal student Arrian, who wanted to make sure that later generations could benefit from his wise mentor. (Thanks Arrian!)
 | A guest post by
|
Thanks, Bobby! Love how you structured this by reading order. That is such an underrated detail. Starting with modern and accessible books before diving into the ancient texts makes Stoicism feel much less intimidating.
The common thread across all seven, focusing on what you can control and mastering your interpretation, really shows why this philosophy still resonates today. Such a practical and thoughtful guide!
I hadn’t heard of On the Shortness of Life before, but your recommendation really caught my attention. It sounds impactful, especially with how it reframes time and how we spend it. I'd like to start with this one. Thanks so much for the great recommendation!