The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage

Ryan Holiday’s The Obstacle Is the Way is a superb primer on the Stoic principles. For one thing, at 224 pages, it is less than half the size of the last book I read on the same theme, Derren Brown’s superb Happy. This is by no means a bad thing, however, for while Brown’s book delves into the history of Stoicism and man’s eternal search for that which will make us happy, Holiday’s is a quicker, lighter read, but one that packs a hell of a punch. The gist of the book is that if one applies the principles of Stoicism carefully and mindfully, then no matter what happens (good, bad, or indifferent) then it becomes possible to deal with the highs, lows, and plateaus of life with equal poise and calmness. Obstacles, Holiday posits, represent opportunity, and should be welcomed rather than feared, for they offer us chances to grow and become more than we currently are. There’s nothing really new here, and I say that without being critical. The tenets around which Holiday builds his case are thousands of years old, being drawn primarily from Epictetus and Marcus Aurelius, among others. The great success of the book is its ability to distill these concepts down into usable, everyday ways of thinking which can benefit each and every one of its readers, if they are disciplined enough to apply them to their own lives. It points out (quite correctly) that the problems faced by the average Greek or Roman citizen were, at their core, fundamentally no different than the ones that vex us today, for they are based upon the same old negative emotions: fear, jealousy, anxiety, greed, a desire for celebrity, and so forth. Marcus Aurelius, one of Rome’s five so-called “Good Emperors,” wrestled with all these issues and more on a daily basis, and used Stoicism in order to successfully conquer them…and himself. There are very good reasons why Meditations is still read so widely (and re-read so frequently) today. I have returned to the book regularly ever since I discovered it as a teenager, and will probably do so for as long as I live. These truths are timeless, and invaluable. Holiday refers to the Stoic philosophy as “an operating system for living,” which seems very apt in this digital day and age. If that is indeed the case, then The Obstacle Is the Way serves as an introductory manual for that operating system, a primer that helps one get to grips with how it works. Some of the complexity and nuance may be left out or abstracted, but the thrust of it is covered succinctly, with plenty of easily understandable contemporary examples to clarify things. I highly recommend this book to anybody who could use a little help in dealing with the stresses and strains of everyday living…and at the end of the day, isn’t that all of us?

Excellent read. This book has been especially helpful during this time in my life. I like the stories, historic references. This manner of approaching obstacles has value with solution. I've listened to Ryan Holiday's podcasts daily and look forward to reading more of his books. He is an excellent speaker and one of my top- favorite writers.

No doubt, you are trying to get ahead in whatever ‘getting ahead’ means to you. But so often an obstacle seems to stand in your way. Yes, there are a few people who report having planned their charmed life or their business success and had it unfold almost exactly as planned, and with style and elegance. Amazing, but never true. Most people blocked by the obstacles of time, money, connections, opportunity and more, do nothing. This book has a fascinating take on ‘being stuck’ – it is a primer on how to turn adversity to advantage, as the subtitle explains. Let me state upfront – I am bored by motivational talks and books. I find very little about them interesting or useful twelve hours later. This book is not a motivational text, though it is motivating as many good books are. The “Ancient Art” of the subtitle is referring to the wisdom and insight of the Stoic philosophers. These writings or thoughts influenced all the people Holiday uses as examples of this approach to obstacles of life. The circumstances of these people would leave most disoriented, reactive, torn and even paralyzed. As Holiday shows “some seem to turn those very obstacles, which stymie us, into launching pads for themselves.” Knowing that there are heroes doesn’t help us to become heroes, but knowing how they became heroes, does. The value of this book is that it offers an ancient and profound method and framework for understanding, appreciating, and acting in the face of the obstacles life throws at us. Turning obstacles into the way forward takes many forms. For the great Athenian orator, Demosthenes, it was a relentless drive to improve himself through action and practice. For Abraham Lincoln it was humility, endurance, and compassionate will. In each case, all the people cited in this book were not born with the attributes it took to succeed, and many faced unimaginable horrors, from imprisonment to debilitating illnesses, and of course the day-to-day frustrations we all endure. So, what did they do? “They had the ability to see obstacles for what they were, the ingenuity to tackle them, and the will to endure a world mostly beyond their comprehension and control,” Holiday explains. The perspective is not a self-delusional, positive and happy one, ‘this is not so bad’, but rather, ‘I can make this good’. The starting point is maintaining a state of mind that one of Holiday’s examples, the extraordinary businessman, John D. Rockefeller, had perfected: cool headedness and self-discipline. When America send the first astronauts into space, they trained them in one skill more than in any other: the art of not panicking. When people panic, they make mistakes. They just react, but not to what they need to react to, but to their survival hormones. At 150 miles above Earth, panic is suicide. Panic had to be trained out of the astronauts and it does not go easily. It must be trained away, through persistent, repeated attempts at not panicking, until you don’t. Talent isn’t the most important characteristic for success, grace and poise are, because these precede the opportunity to deploy your talent. The action after the panic allows for a change of perception that is a prerequisite for right action. George Clooney spent his first years in Hollywood getting rejected at every audition. He desperately wanted the producers and directors to like him, and they didn’t. He blamed them for not seeing how good he was. His life changed when he changed perspective, from self-centredness to that of other-centeredness, not possible in panic mode. Producers need to find the right actor to cast in their film, and they all hope that the next person to walk into the room is the right actor. When Clooney realized that he was the answer to their prayers, not the other way around, his performance improved and so did his career. Consider the refusal to fund your company. I could be an obstacle, or a call for a change of action. Getting the person to fund you this isn’t up to you, but the decision to refine and improve your presentation is. Consider the number of exceptional businesses started during depressions or economic crises. Fortune magazine was founded soon after the crash of 1929. Hewlett-Packard, and Revlon in the Great Depression. General Motors in the panic of 1907. Microsoft in the recession in 1973-75. LinkedIn during the burst of the dot-com bubble. Half the companies in the Fortune 500 were started under adverse conditions. Rather than focus on the difficulties of an economy in free-fall, they focused on what they needed to do to succeed, and that produced the difference. This difference requires presence of mind. Andy Grove, former CEO of Intel, said “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.” In like fashion, great individuals find a way to transform weakness into strength. This is essentially a very practical book which will introduce you to a wealth of important ideas beyond what I have introduced in this column. They will be of extraordinary value as you try to facedown business crises. Readability Light --+- Serious Insights High +---- Low Practical High -+--- Low *Ian Mann of Gateways consults internationally on leadership and strategy and is the author of the soon to be released ‘Executive Update’.

Awesome read. Inspires a better perspective on life’s challenges, and life lessons to improve all aspects. I highly recommend reading this book!

Drawing from the lives of historical figures like Marcus Aurelius, Ulysses S. Grant, and Amelia Earhart, he reframes obstacles not as roadblocks, but as the very path forward. He outlines three core disciplines — Perception, Action, and Will — and shows how mastery in these areas transforms challenges into catalysts for growth. As a coach, I often say that discomfort is a sign of growth. Holiday goes further — showing that the obstacle itself is the growth. This book isn’t about ignoring pain or pretending adversity doesn’t hurt — it’s about choosing our response, reclaiming our agency, and finding power in what we can control. If you're stuck, frustrated, or just facing a tough season — this is a mindset reset. A great read for anyone who leads, serves, or wants to grow stronger through struggle.

For me not just an intro but a good refresher of the philosophy which I have just read at the right time. Clear and heady to read even hard at times to put down

Muy buen libro sobre estoicismo y cómo afrontar los obstaculos en el día a día. Escrito muy bien y en capítulos cortos que no se extienden innecesariamente.

But (way) better is to actually read the books, author is basing on.

Questo libro è incredibile. E' stato il mio primo contatto con il mondo dello 'stoicismo' e Ryan Holiday scrive egregiamente. Si tratta di un libro che va letto ed elaborato, meglio se più di una volta. Quando mi trovo ad affrontare una nuova sfida o delle difficoltà lo rispolvero per trovare nuovi consigli o spunti di riflessione

Really one of the best books I've read and will make you see setbacks and struggle in a completely different/empowering way!

You should really get the hardcover, i love it. It's the original book copy. From the begin of the book you get so many great insights. It makes you feel like you did a good thing by purchase it within the first 5 pages of the introduction. the book gives you clarity, helps you in overcoming, make you understand how to overcome not just by giving you an answer but giving example/story.