Ryan Holiday’s bestselling The Obstacle is the Way introduced readers to the Stoics’ unique blend of practicality and wisdom. This new one, The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living, widens our view on the school of Hellenistic philosophy, founded in Athens in the early 3rd century BC, and shows that it can be applied to any problem, from managing failure to getting what you want. In short, the ideas of Seneca, Epictetus, Marcus Aurelius and others are just as relevant to doers and thinkers in today’s world. He talks to Esquire about what inspired him to write this latest book.
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You worked in marketing for a fashion brand – two industries not renowned for zen-like behaviour. Can you explain?
I think that’s one of the big myths and mistakes about philosophy. To the Stoics, philosophy was designed for everywhere and anywhere. When one thinks, “philosopher” they don’t think emperor, but that’s what Marcus Aurelius [Roman Emperor, AD121-180] was. They don’t think slave, but that’s what Epictetus [AD55-135] was. They don’t think merchant or soldier or boxer, but that’s what Zeno [BC334 -262] Cato [BC95-46] and Cleanthes [BC330-233] were. The point is: philosopher is about your mind, not your profession. So I would argue that bringing a philosophy of clarity, effectiveness, and serenity were incredibly helpful then, and are incredibly helpful now, whether I am sitting down to come up with a marketing plan for a new t-shirt or sitting down to consider my own mortality.
Did your interest in personal development help or hinder your career and how?
It’s interesting, I don’t see how it could possibly hurt. The better you are as a person, the more ordered and sensible your life is and the better you will be professionally. As I wrote in my last book, perfecting the personal regularly leads to success as a professional, but rarely the other way around. And speaking of that book, I’ll give you an example how I think it could’ve easily been not as good as the final product if I’d let any sort of arrogance and overconfidence sway me in the creative process. I’d argue it’s my study of philosophy, and the Stoics in particular, that helped prevent that. When you study philosophy you inevitably learn to confront yourself and fight your lesser traits and impulses — “know thyself” as Socrates’ dictum goes — which by definition helps you in your career. You connect better with people, you are less sensitive to feedback and see it objectively, and you are more composed in a crisis. You are also more aware of your strengths and weaknesses and that helps you to both prioritise and delegate. 
Why did you write this book?
I first discovered Stoicism by chance when I was 19 years old and it was one of the most pivotal moments in my life. Unlike the dry philosophy I encountered in college, Stoicism is practical — it aims to help us overcome problems in life. It has strengthened me in failure, comforted me in pain, given meaning to events, and cautioned humility and conservatism in moments of success. It has been a philosophy of life that that’s been embraced by great men and women of history but few people today have had the chance to be introduced to. And this is exactly what we wanted to do with The Daily Stoic. We are basically trying to say: Look, this is a tool to help you achieve self-mastery, resilience and get you to live a great life. And again, most people probably don’t know that the Stoics were all men of action: Emperor Marcus Aurelius was the most powerful man in the world at the time, Seneca [BC65-AD4] was Rome’s most prominent powerbroker and a tutor to Emperor Nero [AD37-68]. Epictetus was a former slave who became an influential teacher. And we are incredibly lucky to have access to their wisdom millennia later.
How did you select your meditations?
The quotes and passages come from books that you normally do not read only once and forget. One of the books, Meditations by Marcus Aurelius, is a book that I first bought exactly 10 years ago and have read easily over a hundred times. The same is true to a lesser extent with the other two main Stoics, Epictetus and Seneca whose books I’ve also devoured. You have to keep coming back to the lessons — you can’t just read them once or twice. So these are books that I have returned to multiple times and underlined and marked important passages that have struck me. When we began writing The Daily Stoic we already had a great starting point as both me and my co-author, Stephen Hanselman, who translated them, had multiple quotes and passages that we wanted to introduce people to.
Why 366?
One for every day of the year and an extra in case it’s a leap year is the short answer. The longer answer is that Stoicism is about ritual and routine and the idea of having a single, short exercise to do each morning is a great way to help people start their days. This was the format that we decided was the best way to introduce the large variety of quotes and ideas from the Stoics to modern readers.
Give us a good starting point of five things we can do to live better now
There are few lessons from the Stoics that I think can be beneficial to anyone. In its simplest form Stoicism essentially says: We do not control what happens, but we choose how to respond. And the Stoics would say that we need to respond virtuously, whether a situation requires patience, strength, courage, justice, humility or any of the virtues. I think that’s the first thing that if we remember to apply on a consistent basis can make life better for all of us. The Stoics also advocate journaling in the morning — examining our behaviour and asking ourselves the tough questions. They also tell us that a given situation is up to us to determine if it’s good or bad. It is us who are labelling something positive or negative. The Stoics also advocate something that usually shocks most people today and that is to meditate on our mortality. Counterintuitively, reminding yourself that you are going to die is one of the quickest ways to get you to start fully living. And one final exercise that I recommend would be simply going out in nature and meditating on the immensity. Realising how small we are in relation to everything else. It’s a very humbling feeling. There is no room for ego standing beneath the giant redwoods or on the edge of a cliff or next to the crashing waves of the ocean.
What does happiness look like?
One way to define would be as having the freedom to live your life on your own terms. And as I write in The Daily Stoic, big part of that comes from the ability to have the self-awareness and putting in the time to reflect on what’s important to you — what matters and what doesn’t as opposed of doing things out of habit and sleepwalking through life. For example, for me personally, happiness is time reading, writing, spending time on my farm. But it’s different for every person.
Could you recommend three to five other books that will help set us on the path to fulfilment?
Absolutely. I hope the readers of the book are inspired to continue their study of Stoicism and practical philosophy and pick up the three main Stoics. For specific books, those would be the Emperor Marcus Aurelius’s Meditations, Seneca’s Letters from a Stoic and Epictetus’ Enchiridion. Meditations are essentially the private journal of the world’s most powerful man extolling himself to be better, more just and humble. I think it’s the greatest book out there. Letters from a Stoic is made up of letters of advice that help us face and deal with grief, wealth, poverty, success, failure and other problems. And then we have Enchiridion, which translates as a ‘small manual or a handbook’ and it is exactly that. It is the perfect introduction to Epictetus as it is packed with short Stoic maxims and principles. I would definitely recommend all three.
And also I would strongly recommend Viktor Frankl’s Man’s Search for Meaning which is essentially a short book about his experience in concentration camp and finding a way to find good and meaning from it. I think it’s the ultimate metaphor for life: that we have little control over our circumstances, complete control over our attitude, and our ability to make meaning out of the things which happen to us. It’s such an important book.
What’s your next book idea?
I always keep the next idea a secret for as long as I can, but the book is done. It went into the editor last week.
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The Daily Stoic, by Ryan Holiday and Stephen Hanselman, published by Profile Books, is out on November 3rd
