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.

A great pep talk drawing upon the strengths of ancient stoicism. Reminds me of Ayn Rand's objectivism; however, lacking her audacity to hope for idealogical romance and capitalist ingenuity and the market rewards for greedy innovation. In no way is this pep talk book better than any of Ayn Rand's works, but this book does successfully, with great simplicity, invigorate readers like me to lean into the fear. Fear is an illusion. That alone is powerful. But this book is not all powerful. It is just a booster shot. I think Ryan Holiday, from his peppered comments throughout the book, might be an atheist and a far left socialist activist. To me, there is a sense of higher-ness (and hope) missing from this book because of the inherent walls of his ideology. At least Ayn Rand's objectivism gave hope and spoke out about the failures of communism. It's just bizarre how we continue to fight the same battles. I appreciate Ryan Holiday's arguments and I find it interesting to read the philosophical quotes he provides, ones that gets communist activists jazzed up. Honestly, on their own, they are intoxicatingly beautiful. But no communist society, let alone a single community, has stood the test of time. But I digress into matters that already prove themselves. There's no faulting Holiday for peppering the book with progressive leftist teachings. He comes across as completely honest about his position and I give him heaps of credit for that bravery: demonstrating that he practices what he preaches about facing fear and obstacles. I recommend this book as a booster shot to remember that life isn't supposed to be comfortable: it's war. Whether explicitly or implicitly, we're all choosing which side we're on. Regardless of which side one sits or moves on, one should actively go all in and be counted. Judgment day is coming.

I have been a long time follower of Ryan and his work so when this book came out I grabbed it. Ryan gives a great overview of Stoicism and applies it to our everyday lives. For those of you who don’t know, Stoicism is a philosophy teaching individuals to improve their moral and ethical well-being come what may. He takes example after example of great leaders who followed Stoicism and used it to leverage their problems to come out with solutions and to emerge as better people. Why you should read this book Ryan talks about something we all love to talk about: Our problems. Problems are something we face daily on both a small scale and a large scale, but instead of magnifying our problems, he shows us how to use these to our advantage. Instead of sulking or feeling bad for ourselves, he shows us how to find the benefit of the tragedy that has just befallen us and actually utilize it to make us better people. He shows us things from harnessing our negative emotions and using them as a catapult, to being aware of the fact that we are mortal to empower us to live each day. Who this book is for I don’t know a single person who wouldn’t benefit from this book. Every day we are faced with problems and we can always control how we view them and what we will do in the middle of them. This is an empowering book, if only you will take the lessons and start using them. How I applied it in my life: The other day I had a situation happen to me where I could have panicked but instead I embraced the problem and was able to face the obstacle, re-frame it in a positive light and work out a solution. Here’s what happened: I was in Houston and about start the 3 hour drive back to Austin when my car engine started smoking. I pulled over and figured out it was either the radiator or a hose and walked to the gas station to get water to figure out where the leak was. On the way there, I thought I may have to hitchhike back to Austin and leave my car there, depending on how bad the problem was. When I returned to my car, I realized I didn’t know where to add the water to, so my hitchhiking idea popped back into my head and I went back to the gas station to get cardboard and a marker. With my new “Need Mechanic” sign, I had help within 5 minutes. I headed to Autozone and found the hose I needed and ALSO happened to find a mechanic. I got to use my hitchhiking skills, learn more about how to fix my car and practice some Spanish (my mechanic was Mexican and only spoke Spanish). I could have been stressed, but I viewed it all as an adventure and it gave me energy and great ideas to get through it. Ryan explains how to re-think the situation in a way that will empower you to come up with a solution, where a lot of times we paralyze ourselves by getting stuck focusing on the problem, how bad it is and how unfair it is. This book makes you re-think your problems, turn them into obstacles and leverage them to a solution that will carry you further than you would have ever gone without having the “problem” in the first place. Another situation where I have used knowledge from the book….My work started putting some really heavy demands on me (whose work doesn’t) and at first I had a negative reaction to this thinking about how unfair it was. I started thinking of some concepts Ryan talked about and I re-framed the issue in my mind, was able to identify the areas that were causing work issues and delays, and offer proactive solutions by focusing on positive business outcomes. Three points i found most useful in the book 1. Use the idea that we are all going to die someday to enable you to live each day to the fullest. This was key for me since My mom passed at the young age of 47. 2. We can’t control every situation, but we can control our thoughts about them and our feelings. This allows us to ‘let go’ of so many things we worry about and focus on creating solutions. 3. Use our “negative”: feelings toward something to propel us forward. Many times we allow negativity to paralyze us, but we can use it to fuel us and get us to a better position than we would have been without the problem. I know I'll be revisiting this book in the future. It was exactly what I needed right now.

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.

The premise of this book is great: instead of trying to avoid obstacles or complaining about them, embrace adversity and learn to thrive in spite of it. The first few pages were like an inspiring halftime talk from a football coach, and they had me excited and ready to take on the world. As I delved further into the book, I found that the principles of Stoicism are incorporated in a smooth, teachable manner (so I didn't feel like I was being lectured incessantly about Stoic philosophy) and each chapter starts out with a thought-provoking quote. The author's writing style is direct and easy to understand, and multiple times I found myself highlighting a phrase I found impactful. In spite of these assets, I ultimately felt that the book fell short. Like his mentor Robert Greene, the author weaves in stories of famous historical figures to illustrate each lesson. Unlike Greene's books, however, I found this book's analysis to be quite superficial. For example, in the chapter titled "Channel Your Energy" the author brings up Toussaint Louverture, the fascinating individual who led the only successful slave insurrection in history that led to the creation of a nation. I was expecting an exciting tale from Louverture's life, yet the author simply referenced him for one paragraph to say that his name meant "the opening" because he was "fluid" and "uncontainable." That's it? Why even bother to bring him up? Many, many times the author would bring up a figure from the past only to mention a brief, shallow connection to the chapter's topic before re-engaging in his own pontification, which for the most part revolved around challenging the reader to stop "playing video games" and get off the couch. This might be good advice for some, but not every reader is sitting in front of a PlayStation wondering where life went wrong and awaiting a tongue-lashing from the author. Although the writer has a good voice and I enjoyed his style, there were times where I thought the book could have benefitted from much better editing to tease out some of the fluff. When I read the phrase, "whatever you're doing, it's going to be harder if your plan includes defying physics or logic" I found myself thinking, "no kidding? I'm glad I paid money to read this." Some of the stories were a little less than factual. Was Antietam a huge victory for the Union in the Civil War? It's been a while since I've taken a history course, but it was my understanding that Antietam is considered by most to have been a bloody stalemate. Also, the author made a good point about Obama handling the Reverend Wright fiasco pretty well with a great speech, but I think it's a stretch to say this "propelled" Obama into the White House. I even found some of the author's statements to be contradictory. When describing Jack Johnson's boxing match against the Great White Hope, he said Johnson was "smiling, joking, playing the whole fight" in response to the racial tension of the crowd because "there's no value in any other reaction." Really? Well then why did you praise Joe Louis just a few chapters before for making a point to show no emotion at all during his boxing matches, also in regard to racial tension? Selectively choosing people or instances from history to back up your beliefs leads to inconsistencies, of which the book has many. Demosthenes is praised for not giving up and becoming a great orator, but Jefferson is praised for giving up on becoming a great orator and instead focusing on writing. Well, which is correct? If you want to succeed in politics and aren't a great orator, should you practice and never give up until you succeed, or acknowledge your weakness and focus on becoming a better writer? The truth is, there are many paths to success and ways around obstacles, so many of these so-called principles or rules make sense in one context and are valueless in another. Even so, the author deserves credit for putting together a considerable list of great quotes, providing an overarching yet flawed framework for applying Stoicism to your daily life, and occasionally saying something inspiring that prompts the reader to action and inspires the belief that obstacles are not to be cursed but embraced and overcome.

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’.