100 books like Enchiridion

Seneca was one of the last of the ancient Stoics who lived during the time of Nero. Towards the end of his life, he wrote several letters to a young prefect, Lucilius. These letters were not just meant to be read by Lucilius but the generations to come as well. Seneca’s letters are well written and cover a wide range of topics as they relate to the art of living. These essays are a ‘how to’ guide to living.

Why this translation? Although there are 124 letters in all, modern translators tend to translate just a selection. Robin Campbell is no exception. I chose this translation because it is as good as any and it is not pricey.

Ryan Holiday, like Steven Pressfield, is a no-nonsense writer whose words inspire you to start that project you’ve been putting off.

Already started it but running into some, well, obstacles? Holiday describes in his book how obstacles are a good thing and inspires us to look for creative solutions. This book made me reframe how I look at challenges, both personally and professionally.

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.

While riding on the New York subway one day, the young woman sitting next to me was reading from the so-called “Little Black Book” (a collection of daily thoughts often read by members of Alcoholics Anonymous). After closing the book, she pulled out this very edition of Marcus Aurelius and I could not help but comment to her that she had made a great choice. Not only does the theme of the “Serenity Prayer” go back to Stoics, but Marcus Aurelius’ Meditations (literally titled “To Himself”) show the thoughtful and meditative side of Stoicism. In addition, Marcus Aurelius seems to be practicing what we now call spiritual exercises. Last, what is especially striking is that the Emperor Marcus Aurelius wrote many of these entries while he was stuck on military campaigns; thus, we see up close a man utilizing Stoicism to grapple with the messiness of life.

Machiavelli is often despised as the man who promoted both authoritarian leaders and the notion that the ends justify the means, but this is to misunderstand the importance of the context within which he was writing: 16th century Florence – which was besieged by enemies on every side who proclaimed adherence to the Christian faith but acted as monsters. Machiavelli’s writing made two things clear to me. First, leaders and leadership cannot be understood if you abstract them from their context – when political morality is a contradiction in terms then leaders must be wary of sacrificing their followers for the sake of that same fallacious morality. Second, he lays out how dictators obtain and retain power – and in doing so establishes what we need to do to stop them or remove them. 

The insights in this groundbreaking book apply across the board, from social and family life to interacting and managing others in organizational life.

What factors are at play when people of high IQ flounder while those who are more modestly endowed succeed? Goleman argues that the difference is Emotional Intelligence, which, as he explains, comprises empathy, effective social skills/communication, self-awareness, self-regulation, and motivation.

I’ve watched too many of the allegedly best and brightest, tough-minded executives flame out because they failed to rein in emotional impulse, read others’ feelings, or handle interpersonal relationships. The skills are learnable, and in today’s asymmetric, hybrid, matrixed organizations, they are essential for success.

Kleiner’s Core Group Theory was an aha moment for me, because it teaches senior leaders how to use their power well. The theory explains how top leaders act on their organisations like a magnet on iron filings: the slightest clue or cue they give ripples out, and is amplified and copied by everyone that follows them. This makes it crucial that leaders are careful about even the smallest behavioral choice they make: their priorities, who they pay attention to, the jokes they make – all of these will be seen as role model behaviors and replicated by those trying to impress. There is no such thing as off-stage for a leader.

The leader’s most important job is to set the right culture for their organization. People will copy what you do, not what you say. This simple little book shows you the truth of that: When Mr Miserable comes to stay, Mr Happy doesn’t give him pep talks. He just keeps on being happy until Mr Miserable is too. As a leader, you need to relentlessly role model the behavior you want, until it finally catches on.

Leaders should develop a philosophy of life—a north star that will guide them through difficult times. This timeless classic by Roman emperor Marcus Aurelius provides a combination of wisdom and practical advice that serves as a reference both for those in a leadership position and for individuals seeking a deeper understanding of their daily lives. Here is a sample: “The longest-lived and those who will die soonest lose the same thing. The present is all that they can give up, since that is all you have, and what you do not have, you cannot lose.”

All the easily-portable volumes in Princeton University Press’s “Ancient Wisdom for Modern Readers” can be read in the time it takes to drink two glasses of wine (along with this book, one of my other favorites is How to Drink by the Renaissance humanist Vincent Obsopoeus).

For all their quarrels, ancient philosophers agree that the art of life is the preparation for death. Nobody expresses that wisdom with more panache than Seneca, a philosopher, financier, tutor to Nero, and playwright.

This selection from his works teaches us how to face the death and destruction that we see everywhere in Rome—and everywhere else too.

I turn to Seneca’s essays and letters for a good reminder to live with a minimum of regret and resentment.