I’ve read several books on Stoicism, including:
A Guide to the Good Life seems like the best introduction to Stoicism that I’ve read. I first heard of A Guide to the Good Life after listening to an interview that Sam Harris did with the author, Will B. Irvine, in his Waking Up meditation app (in which Sam Harris refers to A Guide to the Good Life as the best introduction to Stoicism that he’s read).
Irvine is a philosophy professor who expresses some amount of disdain for the academic field of philosophy. He found Stoicism outside of his work as an academic, while looking for a philosophy of life to put into practice. Initially, he had been attempting to pick-up Zen Buddhism by means of first writing a book about the subject. He started studying Stoicism so that he could have an alternative to contrast with Zen Buddhism in his book. Ultimately, he lost interest in Zen Buddhism, and adopted Stoicism.
Irvine intended A Guide to the Good Life to be a practical introduction to Stoicism for “the modern reader,” and to leave the reader with actionable advice on where to start. The book is divided into four parts: the first covers a brief history of Stoicism; the second covers core Stoic practices and techniques; the third recaps Stoic advice on selected, common-but-difficult life topics, like aging; and the fourth lays out a plan on to begin practicing Stoicism.
I think Stoicism and the Statehouse is an interesting book, but it’s harder to recommend due to the political motivations. The author, Pat McGeehan, is a state politician. Stoicism and the Statehouse is something like an exploration of how Stoicism can be used as an ethical guide for a politician’s behavior. The book is divided into the three parts: the first attempts to cover the history of Stoicism’s evolution and its primary values, the second is a biographical exploration of the life and career of Cato the Younger, and the third recaps behaviors and principles that Stoicism suggests we adopt.
The most interesting part of Stoicism and the Statehouse, I think, is the history (part two of the book). When I was initially learning about Stoicism, I was conscious that every book I read and podcast I listened to had a tradeoff — I could be learning about something else and perhaps Stoicism was a waste of time. It wasn’t uncommon for me to think something such as, “Where these people I should actually attempt to emulate? How did Stoicism work out for them?” I found it quite interesting to read stories of Cato and Caesar battling.
How to Think Like a Roman Emperor provides an overview of Stoicism by way of examining the life of Marcus Aurelius. Each chapter provides some biographical information on Marcus, and then explores associated Stoic themes more generally. The author, Donald Robertson, is a cognitive-behavioral therapist, and he often highlights the commonalities of Stoicism and cognitive-behavioral therapy.
The Daily Stoic has 366 meditations, intended to be used as a daily Stoic devotional. I’m currently reading a passage each morning. This is the second year that I’ve done so.
My only grievance with the book is that it's too easy to read. It takes me about 3 minutes to read each day’s entry, and I spend about 3 minutes with the book each day. I could get a lot more from it if I slowed down, maybe journaled about the topic and quote, maybe started a little book club.
Meditations may be the most common “primary” Stoic text, but it’s not the best introduction to Stoicism, in my opinion. Meditations was never intended to be read by others. It's a collection of personal journal entries from Marcus Aurelius. I could see myself rereading Meditations periodically throughout my life, but in the short term, it’s more likely that I’ll reread one of the first three books I discussed.
I have a book that contains three letters from Seneca: On the Shortness of Life, Consolation to Helvia, and On Traniquility of Mind. On the Shortness of Life and Consolation to Helvia are frequently referenced letters in other texts about Stoicism. Consolation to Helvia is a letter Seneca wrote to this mother to try to cheer her up when he was exiled from Rome to the island of Corsica. On the Shortness of Life laments on how much of our lives we waste, mindlessly. Similar to Meditations, these are texts I may return to more frequently over the course of my life than the modern introductions to Stoicism, but I don’t feel like I got more out of them in a first pass.