10 books like Letters from a Stoic

I often joke that Marcus Aurelius is my brother from another mother. Sure, he was a Roman emperor who, if he’d lived, would be 1,900 years old this year, but the things he wrote in Meditations — his book on Stoic philosophy written for himself between 170 and 180 CE — are perfectly on point. I feel like he’s writing from inside my head, struggling with the same challenges I do. Of course, Aurelius is not so much like me as much as he’s like every human on the planet; he just happened to think and express himself in a direct, accessible way. His “epithets” – guiding principles for how he lived his life – inspired me to come up with my own epithets. Maybe they’ll do the same for you.

Does your happiness depend on the opinion and good will of others? Or can you live a happy and fulfilled life even if others disapprove of you? Do events make you happy or sad, or do your emotions arise because of your thinking—whether rational or irrational? These are the central questions that psychologists Albert Ellis and Robert Harper address in this timeless classic of self-growth and self-care. The authors explicitly draw on the Stoic philosophers, including Epictetus and Marcus Aurelius, as forerunners of Rational Emotive Behavioral Therapy. Of all the books on the subject of living happily, creatively, and meaningfully, this one is near the top of my list.

For me, Montaigne’s thoughts on life and human foibles compare favorably with those of St. Augustine. His insights on the human condition are valuable to anyone inclined to self-reflection on one’s own frailties. Montaigne’s advice on coping with one’s mortality is worth heeding. He counsels that in order to deny death its sting, “…let us deprive death of its strangeness; let us frequent it, let us get used to it; let us have nothing more in our mind than death.” Yet our mortality is only one of many issues he discusses. Montaigne offers up wisdom on everything from fear, prayer and solitude, to the virtues of social intercourse, avoiding unwanted relationships, and educating children.

This was a fellow who tried to do everything right, and yet, in the end, his whole worldly life seemed to go wrong. A senator, a scholar, and an advisor to a king, he found himself trapped in the usual sort of political machinations, and so was sentenced to death. He wrote this book while awaiting his execution. Lady Philosophy speaks to him, and he learns how his character matters more than his circumstances. 

“By Love are peoples too kept bound together by a treaty which they may not break. Love binds with pure affection the sacred ties of wedlock, and speaks its bidding to all trusty friends. O happy race of mortals, if your hearts are ruled as is the Universe, by Love!"

We learn more through stories than through reading about abstract concepts. Lives of the Stoics is the story of the ancient Stoics. Who were they? How did they think? How did they live? If we want to live a Stoic life, then it helps us to know how other Stoics applied philosophy in their own lives: How did they face adversity? How did they handle betrayal? How did they handle prosperity? How did they deal with the ups and downs of life? The tone of the book is more informal and personal rather than authoritative. Yet this is one of the best books on Stoicism. Instead of giving us advice on how to use Stoic principles to live a better life, Holiday and Hanselman give us actual examples of people who lived by the principles and the results they got. If you are serious about practicing Stoicism, you will get… show more.

Once you have some idea of what Stoicism is by reading the Handbook, you will want to read Meditations, probably the most widely read and the most beloved of Stoic classics and deservedly so. It was a journal kept by the philosopher-king Marcus Aurelius while he was in battlefields. Meditations was a personal journal of Marcus, never intended to be read by anyone else. Yet centuries later, it became one of the most widely read books on Stoicism. It is filled with practical wisdom and offers a way out of our daily predicaments and shows us how to live our lives with integrity, beauty, compassion, and reason. 

Why this translation? There are many translations of this book but the one I recommend, especially to newcomers, is Meditations by Gregory Hays. This translation is less literal than most others and very accessible to the modern reader.

It’s important to state up-front that Seutonius is garbage. You need to consider him to be like the National Enquirer or TMZ of his era. He was all about the clickbait; in that regard, centuries ahead of his time. That said, the salacious stories in here are pure fun and inspired Robert Graves in his creation of I Claudius.

This book is really for anyone trying to do anything hard in life – because life is freaking hard. I actually find this to be the single most useful (and nearly best) nonfiction title in my library (of about 2,500 volumes), and it’s useful for everything – but, given that Holiday mainly makes his living writing bestselling books, once again writers enjoy a particular embarrassment of riches here. Also N.B. – contains the secret of life.

Epictetus is the Stoic who inspired the Roman Emperor Marcus Aurelius. Stoicism is the intellectual origin of cognitive behavioral therapy and a way for leaders to train themselves to focus on the things they can change, rather than breaking their hearts over things over which they have no control. The Enchiridion has the virtue of being much shorter than Aurelius’ Meditations, and contains pithy observations and advice like ‘it is not events that disturb people, it is their judgment concerning them,’ and ‘don’t hope that events will turn out the way you want, welcome events in whichever way they happen: this is the path to peace.’ Leaders need to be good at detachment, and Stoicism can provide valuable tools to help.

This book is solely responsible for hooking me on Stoic philosophy, prompting my deep exploration of practical aspects of life in my own book and, most importantly, the application of them to my daily life. William’s writing is easy to follow, and his advice is very practical. I’d advise you to start reading the book from chapter four; and then when you are done with the book, come back to the first three chapters.