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The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph
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The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

4.15  ·  Rating details ·  50,721 ratings  ·  3,480 reviews
“The impediment to action advances action. What stands in the way becomes the way.” — Marcus Aurelius

We are stuck, stymied, frustrated. But it needn’t be this way. There is a formula for success that’s been followed by the icons of history—from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs—a formula that let them turn obstacles into opportunities.
Hardcover, 201 pages
Published May 1st 2014 by Portfolio
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Average rating 4.15  · 
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 ·  50,721 ratings  ·  3,480 reviews

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Lenny D
Apr 21, 2014 rated it did not like it
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 perfuncto
Jazzmin Hunter
Sep 02, 2014 rated it did not like it
Shelves: psychology-crap
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". ...more
May 26, 2014 rated it it was ok
Recommends it for: skip this and read the Stoics
Shelves: self-development
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 ...more
Feb 13, 2015 rated it did not like it
This book was a fucking obstacle. Now I can share the way: Don't bother. ...more
Sam Quixote
Feb 19, 2019 rated it it was amazing  ·  review of another edition
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
Krishna Chaitanya
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 an
J.F. Penn
May 12, 2014 rated it it was amazing
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
Canadian Reader
May 05, 2017 rated it did not like it
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." Ju ...more
Eric Gardner
Aug 10, 2014 rated it did not like it
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 worl
Pedro Vasconcelos
May 04, 2016 rated it did not like it
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 ...more
Brad Feld
May 26, 2014 rated it it was amazing
Shelves: philosophy
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.
Tim Nowotny
May 17, 2014 rated it it was ok
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 s
Jul 26, 2014 rated it really liked it
Shelves: nonfiction
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
Peter Goutis
Aug 12, 2015 rated it it was ok
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 th
Vadims Savjolovs
Mar 12, 2015 rated it did not like it  ·  review of another edition
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.
Lee Klein
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 ove ...more
Dave Ricchiazzi
Sep 21, 2014 rated it did not like it
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 tho
May Non-Fiction book of the Month!

Loved some of the concepts but did not like the preachy tone!
Full RTC...
Isaiah Hankel
May 08, 2014 rated it it was amazing
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
Andrew McMillen
May 21, 2014 rated it it was amazing
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 o ...more
Jun 20, 2018 rated it it was ok  ·  review of another edition
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.
Alex Anderson
Aug 01, 2014 rated it it was ok
Recommends it for: no one
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. ...more
Jan 19, 2016 rated it it was ok  ·  review of another edition
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 te
Olivier Goetgeluck
May 21, 2014 rated it really liked it
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 o
Sep 06, 2016 rated it really liked it  ·  review of another edition
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
Dec 12, 2019 rated it it was ok  ·  review of another edition
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 i ...more
Erin Glover
Nov 16, 2018 rated it it was amazing
Shelves: philosophical
"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 ...more
Kingshuk Mukherjee
May 14, 2014 rated it it was amazing
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
J.F. Penn
May 03, 2014 rated it it was amazing  ·  review of another edition
How to turn every obstacle into an advantage. An exploration of why things can be difficult and the best way to approach obstacles in terms of attitude and action. Full of classical quotes and historical stories, this is weightier than most self help. Certainly no fast read, but one to make you think.
"We shouldn't listen too closely to what people say. We'll find ourselves erring on the side of accomplishing nothing."
Heidi The Reader
The Obstacle is the Way is a quick overview of Stoicism, how the author applies that philosophy to his life, and how folks throughout history have used Stoicism to surmount obstacles in their way. I rather liked it but I haven't read the originals (yet) or know much about the topic beyond this book. I would be interested to see what close friends of mine, who claim to be Stoics, have to say about it. Nudge, nudge, Brad Wagnon.

Like other philosophy books, I found this one to be heavy on the sto
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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 ...more

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