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The Obstacle Is the Way: The Timeless Art of Turning Adversity to Advantage

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A guide not just for overcoming the obstacles that hold us back—but for using them for great benefit

The great Athenian orator Demosthenes was born with a crippling speech impediment and was robbed of his inheritance by cruel guardians. Samuel Zemurray was a poor roadside fruit peddler pitted against the behemoth United Fruit Company. Ulysses S. Grant found himself stuck across the Mississippi river, desperately trying to break into the impenetrable fortress of Vicksburg.

These icons and many others throughout history—from John D. Rockefeller to Amelia Earhart to Richard Wright to Steve Jobs—were often placed in nearly impossible situations that turned out to be the platforms for astounding triumphs. They were not exceptionally brilliant, lucky, or gifted. Their success in overcoming extreme obstacles was the result of a timeless set of philosophical principles that great men and women have always followed.

Now Ryan Holiday unpacks those lessons and reframes them for today's world, building on the wisdom of the ancient Stoics and a rich trove of examples. He shows us how to turn obstacles into advantages, through controlling our perceptions, swift and energetic action, and true force of will.

224 pages, Kindle Edition

First published May 1, 2014

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About the author

Ryan Holiday

68 books12.8k followers
Ryan Holiday is media strategist for notorious clients like Tucker Max and Dov Charney. After dropping out of college at 19 to apprentice under the strategist Robert Greene, he went on to advise many bestselling authors and multi-platinum musicians. He is the Director of Marketing at American Apparel, where his work in advertising was internationally known. His strategies are used as case studies by Twitter, YouTube, and Google, and have been written about in AdAge, the New York Times, Gawker, and Fast Company. He is the author is *Trust Me, I'm Lying: Confessions of a Media Manipulator*, which is due out in July. He currently lives in New Orleans, with his rebellious puppy, Hanno.

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Displaying 1 - 30 of 4,596 reviews
106 reviews50 followers
February 29, 2016
Great advice, everyone: overcome adversity. Just do it! For example, if you have a contract from Penguin to write a self-help book but you have absolutely nothing to say, don't fret. This is an opportunity. You interned for a guy who wrote an anecdote-based guide to being powerful. There's no need to reinvent the wheel! Lay down that same track.

Aside from some of the facts within the actual anecdotes—on which I don't trust he's done appropriate research since each of them are presented perfunctorily and exclusively to evince his successful-people habits (and not to interject any complications of reality)—there is little in this book you couldn't get from Dove chocolate wrappers. It's not bad advice, just banal. I would be shocked if Holiday, a so-called media manipulator, put his heart into this drivel. The pacing, tone, and almost computer-generated writing give the effect of a student trying to meet a page requirement the night before a due date. Here's a sampling:
No one is saying you can't take a minute to think, Dammit, this sucks. By all means, vent. Exhale. Take stock. Just don't take too long. Because you have to get back to work. Because each obstacle we overcome makes us stronger for the next one.


No. No excuses. No exceptions. No way around it: It's on you.
This wouldn't be especially egregious if it weren't the whole book, but it is. That's it, folks. There's no point at which it transcends to advice that will move your life forward. Flip to any page; if it isn't an anecdote about how some famous person got famous by exhibiting a given virtue, it's just more of this run-on about how you have to find the way in which your obstacle is the way. There are no specifics about how exactly one is supposed to tackle "obstacles," which is a ludicrously broad concept, just droplets raining down from the Platonic form of Cant. Rather than actionable instructions, these platitudes are vast like the oceans. They run into each other, have no discernible borders, and are so huge as to be unwieldy, so unwieldy as to be pointless. The only real linkage here is the classical Stoic advice to maintain equanimity. This could have been conveyed in a much more powerful way. Like by the Stoics, for example. (He admits as much in the intro.)

The book revolves around dozens of small, unrelated and intellectually unlinked anecdotes. Seemingly anyone who's ever done something well is an example, contradictions be damned. The most hilarious thing is how poorly-rendered Holiday's history is.
One can trace the thread of [Stoicism] from those days in the decline and fall of the Roman Empire to the creative outpouring of the Renaissance to the breakthroughs of the Enlightenment. It's seen starkly in the pioneer spirit of the American West, the perseverance of the Union cause during the Civil War, and in the bustle of the Industrial Revolution. It appeared again in the bravery of the leaders of the civil rights movement and stood tall in the prison camps of Vietnam. And today it surges in the DNA of the entrepreneurs of Silicon Valley.
No word on whether the Native Americans just got out-stoic'd by the "pioneer spirit." The next time you'll read such a vacuous, half-lidded recitation of Western History, it'll be when your sixth-grader is preparing a report he didn't research enough. I have a feeling that's the case here.

It's vaguely insulting to be told that all obstacles are just a bunch of Oedipal Sphinxes. That's easy to say when your career began with a chance encounter with your favorite author, who announced that at that moment he was really looking for a research assistant to hire, and do you know anyone? Probably harder for the kids in sub-Saharan Africa to really leverage their malnutrition into a fierce and fulfilling career in PR. Fuck this book.
Profile Image for Jazzmin Hunter.
258 reviews17 followers
November 8, 2014
About as useful as starting with a list of amputees, picking out only the successful ones, getting their stories, and then writing a book called "Having a Limb Chopped Off is the Way".
Profile Image for Marcus.
311 reviews292 followers
June 2, 2014
This isn't much more than a superficial repackaging of stoicism combined with some semi-interesting anecdotes and a whole lot of trite motivational affirmations. The book is written in the style of Holiday's mentor, Robert Greene, but where Greene does something rare and surprising by compensating for his lack of personal experience with deep and compelling research, The Obstacle is the Way falls flat. The anecdotes are common and superficial and their ties to Stoicism feel tenuous at best. Then, to make it worse, rather than allowing the stories and quotes from the stoics to speak for themselves, they are always followed by explicit and repetitive advice that just constantly restates the one idea that yes, the obstacle is the way.

I really like Ryan. I think he's done some great work elsewhere. I have heard him interviewed and he is a sincere and positive guy. This book feels rushed and incomplete though.
Profile Image for Sam Quixote.
4,451 reviews12.8k followers
February 19, 2019
Stoicism: the ancient philosophy that teaches mental endurance in the face of hardship. Ryan Holiday explores this outstanding philosophy and how it can help us in our everyday lives in The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage.

So: I flat out loved this book! Stoicism, to paraphrase Holiday, is hard-won wisdom forged in the crucible of human experience, and its lessons are enormously valuable. In brief, they are: to do what is within our power and to accept what isn’t; to find the right action, you must find the right perspective - this is almost always to find the positive in everything that happens to us; learn from mistakes - failure is instructional; not to get overwhelmed by the bigger picture, to focus on the here and now, and to persevere; to be calm and resilient when faced with problems - be objective before acting.

I was surprised to discover that a lot of ways of thinking I already use in my own life are traced back to Stoicism. Maybe I liked this book so much because of bias confirmation? Or maybe such ideas are ubiquitous because they make so much sense - live each day like it’s your last, don’t worry about what others are doing and focus on yourself, think positively, etc.

There’s more obviously but it comes down to: it’s all in your head. And I couldn’t agree more with the idea that philosophy should be practical rather than the preserve of academics only interested in sniffing each other’s farts. The best thing about this very humanist worldview is that it spurs you on to be the best possible you who then goes on to do things, rather than stagnate in fear, depression, sybaritic behaviours, etc.

Holiday relates these lessons through the lives of some of history’s most famous adherents to the philosophy from the Ancients, like Marcus Aurelius, Seneca, Epictetus, and Demosthenes, to the modern day, like Tom Hanks, Steve Jobs and Barack Obama. I had no idea that former US presidents Andrew Johnson and James Garfield started their careers as a tailor and school janitor respectively but it makes where they got to eventually all the more impressive, and they used stoicism to get themselves there.

I won’t run through the list of other famous names and their stories or the more nuanced takes on the philosophy here - if you’re interested, read the book itself - but suffice it to say that I enjoyed it all. The Obstacle is the Way is a fantastic overview of and introduction to a remarkable philosophy that has impressed itself on me completely - genuinely helpful and inspiring stuff! This is rocket fuel for the mind.
Profile Image for Krishna Chaitanya.
68 reviews121 followers
August 29, 2020
It is a short and powerful read.

The problem or limitation I should say with the most of the self-help books is that they try to cover many subjects in a single book and because of this the quality is compromised, but not this one.

The author in his book only tried to cover one important subject or challenge which most people scared of, obstacles, how to turn them upside down and use them to your advantage.

It is apparent from this book that the author is a great admirer of stoicism, philosophy and Marcus Aurelius. Their preachings are sprinkled in each of the chapters which is deeply inspiring.

The author provides 3 facets - Perception, Action and Will namely to embrace/accept obstacles and turn them to an advantage, draw momentum to keep moving forward and face the next challenge.
Profile Image for Canadian Reader.
1,049 reviews5 followers
May 5, 2017
This is a trite, flippant book that does a great disservice to the deep philosophy of the stoics. Replete with references to tycoons and millionaires, it is largely self-help in perky, upbeat, you-can-do-it, rah-rah language. The essential premise of stoicism--that sometimes the only choice you have when you are faced with a dire situation is the attitude or philosophy of acceptance that you can bring to it--has been warped into "there is nothing either good or bad, but thinking makes it so." Just because Hamlet makes this statement, it doesn't mean that Shakespeare was a moral relativist, or that he was advocating that we should be. The hard things that happen in the world do not occur for our own personal growth and "journeys".

Ryan Holiday is apparently known for another popular work (which some have found a bit chilling) Trust Me, I'm Lying. I didn't trust Holiday for a minute here with his Tony Robbins-like exhortations and his superficial glossing over in chipper staccato prose of life's real hardships and injustices. One's attitude and perception do need to be wrestled with in times of great pain and hardship, but such events don't occur to make us better people.

I do not recommend this formulaic piece of self-help schlock. Avoid it!
Profile Image for J.F. Penn.
Author 45 books2,142 followers
May 12, 2014
This is an intelligent self-help book packed with examples from history of people who made it through adversity into greatness. It also offers a system for approaching life as a more average person, turning obstacles into advantages, and using relentless persistence to achieve what you want.

We all face obstacles in our lives, what matters is how we perceive them and work with them to move on. "When we aim high, pressure and stress obligingly come along for the ride," so we have to find ways of dealing with them, as well as the aspects of life that may blindside up with randomness.

Holiday uses Stoicism as a basis for the book, but it's not a dry philosophy book by any means. He makes the words from thousands of years ago come alive through modern example. As someone who studied Greek and Latin at school, I appreciated the 21st century take on the subject. Through perception, action and will, we can achieve despite obstacles. I particularly liked the chapter on 'amor fati,' love of fate.
Profile Image for Eric Gardner.
48 reviews8 followers
July 25, 2018
Early in the book Holiday writes, “This is not a book of gushing, hazy optimism…There will be no folksy saying or cute but utterly ineffectual proverbs.”

He is partially right. There aren't many folksy sayings, but the next 200 pages features a mixture of ineffectual proverbs and utterly incomplete historical rehashes. Holiday is an accomplished thinker and writer, but this book will not give you a comprehensive insight into success or stoicism, but rather a foolishly short-sided view of the world.

If Holiday analyzed the European theatre of WW2 he would forget to mention America's supply chain advantages or Germany's lack of oil. Instead he would focus on Eisenhower's unique ability to "find the opportunity" and see that the solution to the German strategy "was found inside the strategy itself."

That is, by the way, almost exactly the childish and sophomoric analysis he provides.
Profile Image for Pedro Vasconcelos.
46 reviews5 followers
May 23, 2016
Too much vaporware. Some interesting ideas, some nice stoic quotes, but overall it's more like a very long, feel good, bland, blog post. Also, most examples of historic figures or famous people, suffer greatly from selection or confirmation bias. Life is complex and most of the time you cannot pick examples of successful people and attribute their success to specific causes. A lot of the real life examples in this book felt like they were shaped and distorted to fit the autor's narrative and to sit nicely in the few lines each was given. Sometimes I like to pick up one of these books that sit squarely in the self-help category.. they make you feel good, motivated and can be a source of very interesting characters, perspectives and ways of doing things.. this book was not one of them. Cannot recommend it.
Profile Image for Dave Ricchiazzi.
142 reviews1 follower
September 21, 2014
Picked this up after I heard the author speak on a podcast, and thought it would be worth looking into, at the very least for a refresher on the upshots of stoicism. This book contradicts itself, leaves gaping holes in its practical advice, and is yet another apology for the idea that "successful people are successful because they're better people than everyone else".

The author recognizes that there are many factors in life which are out of a person's control, but takes pains to ignore that those factors can contribute wildly to the outcomes of peoples lives. Yes, people can and do bounce back from setbacks. They can dig in, take things in stride and make something out of their loss. Perseverance is a good thing after all. But sometimes those setbacks are timed in such a way, or happen in a set of circumstances which all but destroys hope of regaining lost ground within the span of a lifetime, or whatever lifetime remains for some. Sure, trying to see the best way forward isn't bad advice necessarily, but it does little to acknowledge the systemic issues that may have been the cause of such setbacks.

Holiday's practical advice is pretty much all over the place. Stay calm and judge a situation objectively is the first bit, and that's fine. But his section on action is essentially this: when a situation calls for action x, do action x. Be aggressive when you need to be, be patient when you need to be, be decisive when you need to be and things will work out...or they won't. No clue as to how to learn when aggression is called for over inaction, patience or speed or vice versa. You're supposed to learn that as you go, life being a trial by error experiment, in which any failure is short-term can be simply overcome (note for author: Life doesn't always work like that). Once you overcome those setbacks, repeat the process. Or...don't repeat the process but instead realize that this obstacle is not going to be moved, and you need to find a different way. When is it appropriate to do that? Again, no help.

The end result of all this is that what is required by the stoic is perfect wisdom, and even that is insufficient in the face of uncontrollable variables. Even if you knew when to strike and when not to, things can still get in your way, and if they do, well the least you can do is help others or learn something virtuous. And this is yet another problem.

Helping others and learning virtue are apparently consolation prizes to being deterred from your personal goals. Obstacles in your way causing failure? Well, if you can't overcome it, help others. If you can't overcome it, learn some humility and move on. What about the successes? Are they excused from helping people? Do they not need to learn virtue? Because again, just as uncontrollable circumstances can cause failure, they can also cause success, a point which appears nowhere in the text. His use of Rockefeller as a shining example of stoicism is enough to tell you just how much the stoic values "the good".

His use of Grant and Eisenhower are particularly telling. These were men in control of themselves and therefore were successful. They had to make serious decisions in which countries/the world hinged. What about the people they commanded? What about those little soldier stoics on the front lines of North Africa who were dying while the generals were "learning from their mistakes". What is the advice for the grunt, who is serving their country, but has to follow orders? What advice to those whose obstacles are bullets to the brain?

In other parts of the book, he seems dangerously close to blaming students for their student loan debt, or bemoaning the "safety nets" of our modern lives which have softened his generation. The sad truth of it is, even if everyone was a stoic, greatness would still elude the same amount of people. To do otherwise would destroy the entire notion of greatness. It may make people more resilient, more determined, less inclined to complaining, but it also would make them easily manipulated. Not achieving your goals? Work harder, for however long, at the rate your betters have set for you, and don't complain, because that's useless and doesn't get you anywhere. Except of course, when it will get you somewhere because you should've seen that you needed to zig instead of zag.

This yet another volume like The Secret, which wants to instill the idea that people are successes solely because of their attitudes and their work ethic. Sure, sometimes that is absolutely the case. Sometimes unflappable determination and grit gets you somewhere. But sometimes being in the right set of circumstances in the right time also gets you somewhere.

If you take anything from this book, take that being resilient, being persistent, and having a good work ethic will help you more than not having those things. Any stronger statement falls apart. This was a rant and all over the place, my apologies.
Profile Image for Liong.
120 reviews64 followers
September 13, 2022
I read Ego Is the Enemy by the same author, Ryan Holiday. I rated it 3 stars.

This time I rated this book 4 stars because I learned something new especially when I don't know how to react smartly when I face obstacles in my life.

This book mentions many tools to handle and solve the problems that we are facing every day.

I like his words:

"While others are excited or afraid, we will remain calm and imperturbable. We will see things simply and straightforwardly, as they truly are-neither good nor bad. This will be an incredible advantage for us in the fight against obstacles."

We should focus on what can be controlled and look for opportunities within the obstacles.

We defeat emotions with logic. We try not to perceive but to observe simply what is there.

The author recommends reading Meditations by Marcus Aurelius translated by Gregory Hays.

Profile Image for Brad Feld.
Author 37 books2,345 followers
May 26, 2014
I don’t know Ryan Holiday, but I heard of this book from Tim Ferriss and was intrigued by the description so I decided to dose myself in some stoicism. Dynamite book – I’m glad I put the time in. Holiday covers the topic well in a very accessible way.
Profile Image for Peter Goutis.
73 reviews8 followers
August 18, 2015
I really wanted to like this. Ryan seems like a smart guy. But I just found it tedious to get through. It was very repetitive and "cheerleady" (okay, I know that's not a word).

I can summarize this book in a few words:

Put on your big boy pants.
Push on.
And do the right thing.

Toward the end of the book, in the recommended reading, Ryan states not to read the books about Stoicism but to read the originals. The books about Stoicism aren't worth checking out (and he knows because he's read all of them). I'd take his advice on this one and stick to the original works by Marcus Aurelius, Seneca, Epictetus, etc.
Profile Image for Hamad.
989 reviews1,304 followers
June 22, 2021
This Review ✍️ Blog 📖 Twitter 🐦 Instagram 📷 Support me

“Think progress, not perfection.”

A book that sold more than a million copies, has ~50K ratings and an average rating of 4.15 should be great right? Nah and the top reviews are mostly disappointed people with one stars which should have told me something about it. I came upon this book when I was looking for more Non-Fiction to read and expand my horizons. Matt D’Avella who is one of my favorite YouTubers at this time once recommended it in one of his videos, I knew I was gonna read it then. Also I wanted to learn more about Stoicism which I discovered recently (Not the biggest fan of philosophy) and I thought this book would be helpful, unfortunately it wasn’t!

The problem with this book is that it does provide a few good points but it does so in 200 pages more than it should have been. The points I can take from this book can be summed in a blog post, to be honest I mentioned this book to a friend of mine who is a huge philosophy nerd and we talked about stoicism a bit and I felt it was more helpful than this book.

The language is “Preachy” and the author lets you feel that he discovered a secret of the universe and he wants to share it with us just like the tone used in the book “The Secret” which -I hated- you probably have heard of.

Also the author has a huge problem with Selection Bias when it comes to this book. The examples mentioned are A) the same ones picked by all authors writing about productivity/ Success … etc and B) aren’t really the best examples because if I was in a debate with the author I would have easily won countering those same exact examples. The funny thing is how each book mentions Bill Gates for example from a different angle, Outliers tells us about his 10K hours of expertise he had before becoming huge, The Unfair Advantage is self explanatory and explains the advantages he had over people, The Happiness Advantage tells us how it is always group work and never an individual!

“After all, the brain is a muscle like any other active tissue. It can be built up and toned through the right exercises. Over time, their muscle memory grew to the point that they could intuitively respond to every situation. Especially obstacles.”

This quote also irked me because it shows the author has zero knowledge in the medicine field, “The brain is a muscle??!?!?!” how the heck was that even published? I even tried to think it may not be literal but if it was the case then it shows how the writing is weak!

Also at the end of the book the author mentions that Stoicism is best learned from the older original texts because they are easy to understand and most of the modern adaptations are not that great, this book was actually a proof of that!

“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.”

Summary: I think the book has a few good points but it is not the best place to learn about stoicism. I expected to learn how to use obstacles to move forward too but it did not help with that, it was just example after example of people who did that, it may give a small motivational push and it may not given the fact how the examples were nitpicked in a biased way. The writing may be borderline on the toxic positivity side and for that reason, I think I am not gonna recommend this book for people interested in the subject. Maybe just take the author’s own advice and read some of the original texts like Meditations by Marcus Aurelius!
Profile Image for Tim Nowotny.
1,009 reviews18 followers
May 24, 2014
Maybe I got into it with too much background of the author.
Knowing and linking much of the Tim Ferris stuff I had read the blog post of "How to do a bestseller" which this applies without shame. That in itself would be no bad thing. The bad thing for me starts when there is no depth in this book. It is like having heard a good quote and repeating it over and over and over again.
I like the author and I like stoism. But there is so much more than "It is not important what life throws at you, you still can make it"
8 reviews2 followers
March 12, 2015
This book contains superficially interpreted and simplified ideas of the Stoic philosophy and interconnects them with the anecdotes and modern life examples. Thats it. You will not find there any original idea or even analysis of the Stoicism. Author repeats the same things again and again seasoned with the names and quotes of the great philosophers.
Profile Image for Perry.
631 reviews502 followers
September 2, 2018
The Curriculum: School of Hard Knocks (Highly Practical; No Dr. Phil's Hogwash or Powdery Puff like that of Eckhart Tolle)
A Largely Practical Self-Help Book of Advice from the Ages for Those of Us Who have Come to Hate Contemporary Self-Help Bullshit

I'm not being coy when I say this should be required reading before being awarded a college diploma: a synopsis/collection of philosophy (from the Greeks to the leaders of today) and inspiring stories of triumphs in the face of the trials of life. It could be immensely helpful to the bright-eyed, the bubbly, the go-getters, et al., in coping with the coming obstacles that will surely come his/her way, some of which could even be so devastating that it shatters (or seems to) the personal myth most of us hold so tightly upon entering the working world: a big house, a perfect marriage, 2 straight A kids, and a well-planned career you love and that makes you tons of money.

This is a new perspective coming from many different angles on turning obstacles over, around and about into positives, and maybe to a better way than that shattered myth of me. I go back to this book often and always find a treasure I really need and that I'd forgotten from my first reading.

This is not a feel-good, power of positive thinking, Dr. Phil Hogslappery or Eckhart Tolle Powder of Now Puffery.

It's real and it's really practical.
Profile Image for Lee Klein .
793 reviews837 followers
March 7, 2018
Found this after googling "The Process" during a highly caffeinated Sixers-related research session one day. The Process refers to Sixers GM Sam Hinkie's plan to pull the team out of mediocrity by clearing cap space, developing unheralded young players, establishing a hardworking, fun, trusting culture/environment, and accumulating draft picks by trading current established veterans (and MCW, the previous season's Rookie of the Year) for future picks, using aforementioned cap space to absorb overpaid/underperforming veterans plus picks in exchange for helping teams bail out from bad contacts (eg, Javale McGee's $20 million/year), and most importantly/infamously running out on the floor a team of young nobodies -- guys like Hollis Thompson, Brandon Davies, Henry Sims, undrafted free agents (TJ McConnell), a D-league MVP (Robert Covington), super-bouncy athletic second-rounders who can't shoot (Jerami Grant, Jakarr Sampson), and former first-round players who hadn't panned out (James Anderson, Thomas Robinson) -- and have them compete hard without the stabilizing veteran rotation player presence (formerly Tony Battie, Elton Brand, et al.), all in order to secure a top-5 pick in the draft, ideally the one thing all great teams throughout NBA history have had, something the Sixers hadn't had since Allen Iverson, something teams can only acquire through the draft or free agency (before they built their new world-class luxury home-base in Camden, no one wanted to come to Philly and practice at the Philadelphia Osteopathic College of Medicine on City Avenue, the only team in the league without their own training facility/headquarters): a superstar or two.

A few years after The Process began (with the trade of Jrue Holiday for Nerlens Noel and a future first-round pick that became Dario Saric and their own future first-round pick that had been lost in a bad trade to draft Arnett Moultrie two years before and that ultimately netted the Sixers the #1 overall pick in the 2016 draft, Ben Simmons, two years after they added the #3 overall pick in the 2014 draft, Joel Embiid), the Sixers now have two likely superstars (Embiid is already an all-star starter and Simmons should win Rookie of the Year and develop into a perennial MVP candidate), last year's #1 pick Markelle Fultz (currently injured/bizarrely jacked shooting form), next year's Lakers pick (currently around #10), and enough cap space to add a difference-making small forward, maybe someone like Lebron James. As a Sixers fan since the days of Darryl Dawkins (pre-Moses, I mean), I was very much in favor of The Process, following its intricacies more closely than I had regular season games in the past, in part because it was such a rational, analytics-driven, longest-view-type plan that ultimately had as its goal not making the playoffs every year (and losing in the first or second round, thereby drafting in the middle teens and getting stuck every year with very good players like Thaddeus Young) but drafting and developing game-changing players who can ignite the city and lead the team to the finals at least. But I think I was also attracted to it because it was about rationally overcoming the OBSTACLE of mediocrity (losing in the first round of the playoffs or just missing out each year) and winning championships (multiple NBA titles, ideally). And so the Sixers turned their obstacle (losing) into the way (losing intentionally/pragmatically in the short term, all to increase their long-term chances of winning).

So I've been a little bit interested in The Process over the years -- and then last week googled "The Process" and for the first time considered that Kafka's "The Trial" is actually called "Der Process" in German -- and also I read something about college football coach Nick Saban's "Process," which led me to this book, which I ordered on a whim. I also like reading things like this (pop science/psych, self-help, etc) every once in a while, gleaning whatever the lesson is that will be repeated a hundred times and seeing how the authors go about structuring a book like this. This one takes Stoicism and Aurelius's Meditations and delivers it like "Stoicism for Dummies" but in updated, attractive, readable form. It's structured into three parts (perception, action, will), with each part having between nine and twelve short chapters, each beginning with a quotation, followed by an anecdote from some famous person (Edison, U.S. Grant, Lincoln, Earhart, Gandhi, MLK, Richard Wright, George Clooney, etc), followed by some abstraction on the topic, followed by more quotations, followed by second-person coach-like clipped encouragement-type sentences, often ending with a bulleted list of summarized tactics to help us deal with the obstacle ahead of us, whatever it is. It's a quick, painless, at times thought-provoking read (again, it's basically a collection of quotations and anecdotes), a great model for anyone interested in reducing a classical philosophy to cherry-picked historical stories and aphorisms followed by vernacular translation directly addressing the reader.

I also now know that when confronted by an obstacle, as long as I proceed with complete attention and energy, all my armies deployed, I can choose to go around it, go in the opposite direction, use the obstacle's energy against it, confront it head on with persistence and try to outlast it -- that is, for every obstacle there's like fifteen different contradictory responses possible. But it's interesting to think about in terms of the Sixers' Process and Kafka's "Before The Law" parable, where the traveler wants to gain access to the Law but the door is blocked by a guard with a huge Tartan beard who talks about dozens of other doors beyond his, each blocked by more terrifying guards, and so the traveler begs, pleads, bribes, and then falls silent and waits patiently for the guard to let him in until one day he realizes that he's grown old and somehow no one else has ever come also seeking entry to The Law and so he asks the guard about this and the guard says because this door was only for you and now I'm going to shut it.

The guy seeking entry to The Law in Kafka's tale maybe should've read this book. Sam Hinkie, however, could probably write a better version of it.

Anyway, an atypical read that's made me want to find that copy of "Meditations" by Marcus Aurelius I have somewhere and that seems more valuable as a model for how to write something like this than a self-help obstacle-overcoming handbook in itself.
Profile Image for Isaiah Hankel.
Author 4 books55 followers
May 8, 2014
The Obstacle is the Way digs into how knowledge and reason are in fact the highest good, as well as how to stay indifferent to pleasure and pain and how to respond to the vicissitudes of fortune objectively. The key is to not let your emotions color your perception of the world.

Ryan not only provides a great review of stoicism, he does an excellent job at articulating exactly how this school of thought can be applied to any problems that you might be facing now as you try to advance your career or transition from academia into a new career. He also provides an ample number of takeaways in the book. The Obstacle is the Way goes beyond the philosophy of stoicism simply by making the philosophy actionable. Reading this book will make you take action. Rational action.

If you're looking to:

-Take your career to the next level by getting a promotion (even though someone else is standing in your way)
-Transition out of academia and into a new career to finally get paid what you're worth (even though you don't have any business connections)
-Quit your job and start your own business so you never have to work for anyone again (even though you don't know how to run a business)

...then this book is for you. The Obstacle is the Way is rooted in concrete, everlasting principles, not processes or fads that come and go with the wind. By reading this book, you will understand these principles and you will be able to make use of them to get what you want.

If you want to get ahead, the Obstacle is the Way is highly recommended.
Profile Image for rahul.
105 reviews259 followers
June 21, 2018
I would suggest a rereading of Marcus Aurelius' Meditations instead of this.

P.S. Also I am tired of examples about what Generals did during wars.
Profile Image for Andrew McMillen.
Author 3 books33 followers
May 22, 2014
I don't know whether the author intended it to be read as such, but to me this is nothing if not a motivational book. Rooted in actionable philosophy that seeks to flip readers' perception of any problematic event into an opportunity, 'Obstacle''s inner message is that, ultimately, the only thing standing between success and failure is yourself. His writing style here is sharp, succinct and authoritative, and clearly influenced by the approach of Holiday's mentor – and another favourite author of mine – Robert Greene ('The 48 Laws of Power', 'Mastery'). By drawing on notable historical examples and showing the strategies these well-known figures used to overcome challenges in their lives, the reader is shown a clear path between intent, action and outcome.

A short read at around 200 pages presented in a small 'pocketbook' format, this is a huge and ballsy departure from Holiday's first book, 'Trust Me, I'm Lying: Confessions of a Media Manipulator'. 'The Obstacle is the Way' is a must-read for any thinking human. It's a text that I can easily see myself returning to in times of need, just as I do with 'The 48 Laws of Power' and 'Mastery'.
Profile Image for Alex Anderson.
291 reviews6 followers
August 30, 2021
The formula: repackage a lot of great quotes, mostly from stoic philosophy. Tie together in a small, convenient carry-along parcel that will appeal to a strategically selected customer base. Add annotation of little value to the works of other writers and great men. Throw in the single beat of a drum with the same message over and over, so that we get it. Perform the aforementioned feat of reverse prestidigitation without bringing the material to life in any way or providing significant insight. The result? A document that does not come close to living up to its hype.

I like the guy that Ryan Holiday used to work for, Robert Greene; an author who is controversial, has broken some new ground and takes risks which often result in forging vibrancy, meaning and life into what he writes about. Unfortunately, and this isn't meant to be an armchair-kill-the-bum-judgemental in any way, but I just can't help it because it's so damn obvious: Holiday has stolen some of his mentor's moves without assimilating any of his strengths.

I was really ready to love this work, truly I was. I didn't even get as far as liking it, and as may be evident, I feel bamboozled. The ideas that this book promotes resonate profoundly with those of us who choose, or have no other choice, than to march to the tune a different drummer: use the rough terrain as an opportunity to build resilience, obstacles are stepping stones and disasters can be opportunities to up your game. This mindset exemplifies so much of what some of us spend a large portion of our lives locked in training mode and do battle with ourselves to accomplish. My first emotional response was to throw a 1* rating at this book, this action would perhaps have captured more attention of curious readers looking for a sign of whether to buy this book or not (my theory is that most potential readers look only at extreme ratings of either 5* for brilliance or 1* for crap and don't bother with the inbetweeners) but that would have seemed churlish. It is worth only a 1* rating, but will double that just in the off chance that this work of crass opportunism might be of some small use to someone. Perhaps it will be of some help to start a fire in a lonely fireplace on a cold winter’s night.

So let's cut to the chase, waste no more time, get the review over with and put a pathetic literary creature out of its misery:

This book is simply haggis dressed as filet mignon.

Mr. Holiday's talents potentially lie in other directions, in other job categories, most likely marketing and sales. Don't get me wrong, these qualities don't necessarily preclude good writing.

Good writing just requires something more.
6 reviews9 followers
July 22, 2016
This book is to Stoicism what a Lipton Iced Tea is to a glass of ice water: they share some substance, but the former is saccharine sweet and diluted while the later is bracing and clear.

I can't assess how good an introduction this is to Stoicism for one not acquainted with it. I would argue, however, that Stoicism doesn't require an introduction. Part of the beauty of the "Enchiridion" or "The Discourses" of Epictetus is their clarity and straightforwardness. Marcus Aurelius doesn't employ a technical vocabulary. In the hands of a good translator, they read more clearly today than most business best sellers.

And if you have read any business best sellers lately, you will see the same examples and anecdotes they share used here to clutter and mask the beauty and wisdom of the Stoics. I recommend going to the source.
Profile Image for Kingshuk Mukherjee.
33 reviews35 followers
October 1, 2015
Everyone has written excellent reviews so I'll keep mine short.

This book is stoicism 101, and resiliency 101. When you feel fear, doubt, lost- this is a book that will remind you that your problems are not unique- plenty of people have suffered worse, and flourished because of it.

It may be difficult to wrap our minds around some of these ideas in today's coddled, soft, comfortable society. But cultivating grit, strength, resilience has never been more important.

A quick read, and Ryan's writing style is easy to digest. Very actionable, very instructive.

A large part of the value of his book also lies in how many people he exposes you to through stories and anecdotes.

If you want to explore any of the characters or topics deeper- he has already given you an excellent starting point through the bibliography.

I will refer to this book often.
Profile Image for Tanu.
312 reviews288 followers
February 15, 2023
“If an emotion can't change the condition or the situation you're dealing with, it is likely an unhelpful emotion. Or, quite possibly, a destructive one. But it's what I feel. Right, no one said anything about not feeling it. No one said you can't ever cry. Forget "manliness." If you need to take a moment, by all means, go ahead. Real strength lies in the control or, as Nassim Taleb put it, the domestication of one's emotions, not in pretending they don't exist.”

“Focus on the moment, not the monsters that may or may not be up ahead.”

This is a compelling and practical self-help book that draws on the wisdom of the ancient Stoics to offer a guide for transforming obstacles into opportunities. Holiday argues that the way to success and growth is not to avoid obstacles, but to face them head-on and use them to our advantage. Through a series of inspiring anecdotes and examples from history, he demonstrates how people throughout time have used this approach to overcome challenges and achieve their goals.

The book is divided into three sections: Perception, Action, and Will. In the Perception section, Holiday discusses the importance of changing our perspective on obstacles and seeing them as opportunities for growth. In the Action section, he offers advice on how to take decisive action and turn obstacles to our advantage. In the Will section, he focuses on developing resilience and perseverance in facing adversity.

The writing is clear, concise, and engaging, making complex philosophical concepts accessible and relatable. Holiday's approach is practical and inspiring, providing readers with the tools they need to overcome obstacles in their lives.

All in all, it is an insightful and empowering book that offers a timeless approach to turning trials into triumphs. Whether you're facing personal or professional challenges, this book will inspire you to see obstacles as opportunities and take action to achieve your goals.

Grab your copy here.
Profile Image for Olivier Goetgeluck.
138 reviews50 followers
May 22, 2014
Ryan Holiday has been one of my greatest mentors in life - even though he doesn't know it, his blog starting in 2007 has been a tremendous influence on my life. I've read a lot of books based on his monthly recommendations and he got me started on researching the stoic school of philosophy myself. I will now recommend this book to everyone who wants to get an introduction to stoicism.

"To be a philosopher is not merely to have subtle thoughts, nor even to found a school ... it is to solve some of the problems of life, not only theoretically, but practically."
- Henry David Thoreau

"Most of our obstacles are internal, not external."

"Things which hurt, instruct."
- Benjamin Franklin

Overcoming obstacles is a discipline of 3 steps:
- Perception
- Action
- Will

Sangfroid: unflappable coolness under pressure

"Just say: No thank you, I can't afford to panic."

"This happened and it is bad. => 2 parts: This happened = objective; It is bad = subjective."

What is up to us?
Our emotions, judgments, creativity, attitude, perspective, desires, decisions, desires, determination.

"When we believe in the obstacle more than in the goal, which will inevitably triumph?"

"We talk a lot about courage, but forget that at its most basic level it's really just taking action [...]] all the greats you admire started by saying 'Yes, let's go.'"

Failure is a feature.

"Failure shows us the way - by showing us what IS NOT the way."

"Just one clean movement after another. That's the results of The Process."

"We are A-to-Z thinkers, fretting about A, obsessing over Z, yet forgetting all about B through Y."

"Intertia of success makes it much harder to truly develop good technique."
=> Trust The Process. Focus On Effort, Not Result. Effort You Control, Result The Process Controls => SURRENDER TO THE PROCESS.

"Sometimes a problem needs LESS of you."

Stoics = Mental Athletes.
=> "Their muscle memory grew to the point that they could intuitively respond to every situation. Especially obstacles."

"Don't just do something, stand there!"

"The obstacle is not only turned upside down, but used as a catapult."

31 reviews
September 6, 2016
Taking the reader through a practical and extremely balanced approach for handling failure, The Obstacle is the Way is a must-read for anyone who has struggled with crippling self-doubt, self-pity, and ennui. Through the wisdom of the Stoics and the example of history, Ryan Holiday reminds us that even great setbacks and obstacles are not the end of the world. Rather, they can become the fuel for a life well-lived. If we so choose.

As someone who feels deeply and places great value on emotions as a creative and relational force, I confess I held a bit of a grudge against Stoicism before reading this book. Not anymore though. In MBTI terms, a Stoic is a person whose Fe is controlled, and therefore channeled into healthy and constructive paths, by his Ti. A Stoic does not lose his head over the challenges, pains, and sometimes utter brokenness that life throws at him. Rather, because he takes a moment to assess the situation, he keeps a cool head and overcomes the obstacles that stand in his way. This cannot be done without feeling. Passion is necessary to fire any vision. But passion alone kills. When thwarted, unbridled passion can lead to depression, self-obsession, and pettiness. There must be something greater encompassing that passion to make the vision come to life no matter what obstacles are thrown in its way. This something is the cool-headed logic and determination of the Stoics.

I just lost a bet by admitting how good this book is, but so be it. Reading this was a humbling experience. It forced me to re-examine myself and my choices with honest eyes. I'm grateful to have read it and would recommend it to anyone seeking to discipline their mind. It's not a book of specific steps to take, and if you're looking for a self-help book you might feel like Holiday does no more than throw around trite platitudes. The aim of the book is not to give specific instructions, though. It's just a broad reminder that if we really want to live well, we better get to it. It resets the button on self-pity, and that alone makes it worth reading.
Profile Image for Erin Glover.
450 reviews36 followers
November 16, 2018
"Through our perception of events, we are complicit in the creation-as well as the destruction-of every one of our obstacles." Obstacles are not good or bad. Our perceptions make them that way. Rather, they are opportunities. "A mistake becomes training." Holiday cautions us not to freak out. It doesn't give us more options. We must control our emotions, not pretend they don't exist. Always act with "justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness." We must focus exclusively on what is in our power and let the rest go. When we act, "act with deliberation, boldness, and persistence." Focus on the task at hand--what's in front of you. Be in the moment. What's right is what works. Love everything that happens: Amor fati.

This work is an amalgamation of the Ancient Greek and Roman philosophers Marcus Aurelius, Epictetus, Cicero, Epicurus, and Seneca to name a few, emphasizing the Stoics. There's a great bibliography at the end. It's a truly fascinating book. To think that philosophers who lived 2000 years ago had the same problems we have today is mind-boggling.
27 reviews2 followers
December 13, 2019
Despite agreeing with the overall message of the book, the way the book presents that message is dreary, tiresome and perfunctory. The book relies primarily on anecdotal evidence, which interpreted by Holiday, becomes explicitly romanticised. It becomes hard to believe that all the examples in the book were motivated purely by stoicism and were originally perfect examples of the lessons of stoicism attempts to depart, which throws the authority of the book out of balance. Every example becomes idealised and perfect and repetitious, which in turn makes all the anecdotes tiresome to sit through. Despite the criticism, there were moments or sentences in the book that related and had a certain affect to them, however, these were far and few between and not worth the price of admission. The audio book was even harder to get through as Holiday narrates it himself and sounds permanently like he has a cold and stuffed nose for the entire reading.
It was okay, but spend your time elsewhere.
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