
The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph
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#1 Wall Street Journal Bestseller
The Obstacle is the Way has become a cult classic, beloved by men and women around the world who apply its wisdom to become more successful at whatever they do.
Its many fans include a former governor and movie star (Arnold Schwarzenegger), a hip hop icon (LL Cool J), an Irish tennis pro (James McGee), an NBC sportscaster (Michele Tafoya), and the coaches and players of winning teams like the New England Patriots, Seattle Seahawks, Chicago Cubs, and University of Texas men’s basketball team.
The book draws its inspiration from stoicism, the ancient Greek philosophy of enduring pain or adversity with perseverance and resilience. Stoics focus on the things they can control, let go of everything else, and turn every new obstacle into an opportunity to get better, stronger, tougher. As Marcus Aurelius put it nearly 2000 years ago: “The impediment to action advances action. What stands in the way becomes the way.”
Ryan Holiday shows us how some of the most successful people in history—from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs—have applied stoicism to overcome difficult or even impossible situations. Their embrace of these principles ultimately mattered more than their natural intelligence, talents, or luck.
If you’re feeling frustrated, demoralized, or stuck in a rut, this book can help you turn your problems into your biggest advantages. And along the way it will inspire you with dozens of true stories of the greats from every age and era.
- Listening Length4 hours and 38 minutes
- Audible release dateFebruary 14, 2023
- LanguageEnglish
- ASINB0BT53FNVH
- VersionUnabridged
- Program TypeAudiobook
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Product details
Listening Length | 4 hours and 38 minutes |
---|---|
Author | Ryan Holiday |
Narrator | Ryan Holiday |
Whispersync for Voice | Ready |
Audible.com Release Date | February 14, 2023 |
Publisher | Penguin Audio |
Program Type | Audiobook |
Version | Unabridged |
Language | English |
ASIN | B0BT53FNVH |
Best Sellers Rank | #336 in Audible Books & Originals (See Top 100 in Audible Books & Originals) #5 in Philosophy (Audible Books & Originals) #8 in Motivational Management & Leadership #15 in Business Motivation & Self-Improvement (Audible Books & Originals) |
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Storytelling has been around since the beginning of time, but actual mass communication has been around for a very short time (relatively). It looks as if the "paper book" business will become a specialty- if surviving at all. I know that Ryan knows this as he has always been quick to lend an idea, do some digging and most important- analyze and decide. As he uses as an example in his book, he pulls an Amelia Earhart and ACTS. He can talk about Tesla in the same sentence as popular games on the meat markets in early Chicago. He has read (studied) Marshall McLuhan to Malcolm Gladwell. This rabid quest to find out and face his own soul searching path- has delivered a perfect book for the RIGHT PERSON. This is not Chicken Soup for the Soul.
Ryan has done WAY more and influenced WAY more decisions than he would ever talk about, but has helped untangle talent and communication complications (i.e- market properly) using many of his methods he developed under Robert Greene and even 50 Cent and Tucker Max. He helped in stealth, but in critical ways, to launch, maintain and capitalize on #1 Films, TV Shows, YouTube and MANY multi platinum musical artists. I can vouch for it myself.
It is always amazing to read a review somewhere when that person has never faced down rejection and fear and can criticize anyone for at least putting their thoughts and ideas out there for judgment. To do that, when the WORLD is telling you that finishing college is the only way to go and you have the same people close to you saying that you will fail- it truly was an Obstacle to overcome. It only got more intense for Ryan, but his lessons are earned. He was led to the water, but unlike most people, he drank. How can you question the message, integrity and courage of that? Steven Pressfield, one of our generations best and most diverse authors, has called it "The Resistance". Even he endorsees the book on the dust jacket.
The reason that I preface the review this way is to show you Ryan's true accomplishment here- articulating what he has learned, applying it to clear examples people can remember and also help people. There have been big choices in Ryan's life- not the least of which was whether to go in house for a safe "job" or "bet on himself". He DID what he talks about here. It is the true reflection on a part of his life and the methods HE used to combat them. This is especially important for a generation who "has ADD" and can't relate to the past. At 22- I think it would be silly to not monitor this refreshing voice and mind as he progress'. He actually went and spent time with Dr. Drew after reading his not so best selling books.
Marcus Aurelius is the clear hero in this book, being compared to boxer "Hurricane" Carter (among others), while dealing with your internal power. The ideas and themes of the book seem to come from some Herman Hesse and Tom Wolfe as much as out of print magazines and long dead historical stars of their time. That is what is so attractive. Anyone should find a part of this to relate to. This is especially helpful to someone who wants a quick boost of intellect instead of trying to muscle through a biography (but he def refers to a lot of interesting people I need to read more about). Ryan does not rely on the same tired stereotyped figures from the past, but finds new, more relatable, characters and situations. Athletes, Entrepreneurs, Parents and CEO's, and those looking to look at life in a certain lens, will benefit greatly.
Think you are having a bad day? Open your eyes and you will find out that another historical leader (other than Churchill) suffered severe depression while running the country that may or may not exist depending on his choices- Abraham Lincoln (didn't see a lot of that in the movie). Grant, Nietzsche and Edison all make a story about fortitude and acceptance. A much different approach than looking in a window and imaging you will get the new purse that is in there and moving on. Again- this is intended for action and not philosophy.
Self Help crap would be fine if it worked, but that means there would only be one book- and it would work. Awareness. Dealing with fear and uncertainty. Mindful and deliberate. Shame and guilt. Accountability and results. How did other people deal with this? Only through careful research do these stories become just as powerful to the man who believes that history is a verb as they are to someone just trying to make it through their day.
The point is- you are not alone. In fact, you are not even close to being the first person today to experience multiple obstacles. It is comforting to see how adversity has been confronted in the past. This is a book for those who believe in Realpolitik and seeing life for what it is. I would say it is the actual back up action plan to what a mystical book like the Mayan based best seller, "The 4 Agreements", is. Although the book is very much based on stoic principles it makes no judgements about your belief system in a macro way.
I can see how this book can have some legs for people try to cope with a new world where you have too much or think you have too little- information to ingest. It is a reference book that can be returned to over and over.
Ryan Holiday is an important voice in the book space these days. Mostly because he is willing to actually commit to writing good books as well as growing his digital presence quickly. Non fiction at that age in 2014 is pretty impressive and patient. He can deal w Dov Charney, 50 Cent, Tucker Max and many others- due to his diversity. His "Read to Lead" mentality is refreshing and way more valuable than any class. He has a Best Seller in "Growth Hacking" at the same time, so holding his own with decades older armchair authors, while understanding the generation gap in communication is not such a bad way to describe this book.
And finally...yes- he uses the bible as reference at times..
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He does explain the basics, so it's not a bad book to read if you have never encountered Stoic ideas before, but he doesn't seem to cover the subject in any depth. I'm waiting for him to introduce concepts like Eudaimonia and Apatheia, but this book reads too much like a self-help book for my taste. He's constantly offering military insights, not all of them accurate (The German attack on Poland in 1939 was a series of Kesselslachen, not Blitzkrieg). Lots of them are about American generals, quite a rich field where you can find many good examples, but after a quick introduction of Sherman (for example), he briefly discusses his personal qualities and he then moves on. Sherman wasn't a stoic (He was a Catholic as an adult), it's as if the author is trying to find things that can be used to support his views. Sherman was mired in controversy several times in his life and had a nervous breakdown in 1861. He was an effective general but not a good choice to support the book's narrative. This book is more like a magazine article or an essay written by someone who knows nothing about the subject but has researched it well on-line.
There are a lot of better books to read on the subject that offer more depth and better insights. I'd not recommend this book to anyone who showed any interest in the subject.

The man is a tv marketer by background - he knows how to fool the masses. And he has somehow managed to get his online badly written life changing course printed.
He basically takes a few basic stoic concepts - don’t worry about what you can’t control, work hard, remain positive etc - and spin a book out of it. Throw in the names of Marcus Aurelius and Seneca along with some modern anecdotes and you are deemed a genius, according to a few people on the back (who clearly haven’t read the book or are part of the self help pyramid scheme)
The anecdotes themselves are horribly cliché. Just name drops people that everyone will know such as Edison, Lincol, Eisenhower, the Lakers (marketing 101 - don’t lose your audience). The bits and bobs of history are so basic and sometimes just wrong - I’m not sure he even bothered to google some of it.
The attempts at motivation amount to little other than “are you ready to go to work? Let’s get to work!”
The writing is blatantly dreadful and nauseating “Lincoln possessed an inner mental fortress that girdered him” Jesus.
It might seem like a good book if you are under 20 and haven't read any self help books before but if you’ve ever read any few before this, you will be quite disappointed with this.

The book is then subsequently sectioned into 3 parts on (i) perspective, (ii) action and (iii) will/perseverance. Each part is divided into roughly 8-10 sub sections. Each sub section is several pages long and offers one key insight. e.g. perspective can be objective/subjective or perspectives create opportunities etc etc.
The book uses anecdotes of successful historical figures to validate ideas which includes the use of Politicians (Lincoln, Roosevelt), Athletes (Hurricane Carter), George Clooney to name a few. There is also many references to Stoic philosophers (Epictetus, Demosthenes, Marcus etc).
Overall I agreed mostly with the proposition of the book. I didn't however believe that the anecdotes supply sufficient reasoning to argue these points. It felt that the author cherry-picked case-studies to fit his narrative.
I also tended to find the writing style was slightly awkward and a lot of sentences were of this nature: "leadership requires determination, energy and courage" which by itself often seemed irrelevant. The author also feels the need to use 2 descriptive words at all instances, e.g. "It's easier to persist in our efforts and actions than to endure the uncomfortable or the painful"
Furthermore, if the reader has read about Stoicism before (e.g. The Ancient Art of Stoic Joy by Irvine) then much of the Stoic ideas are recycled. For an introduction to Stoicism with logical arguments I would recommend Irvine (5* read).
To conclude I feel the overall idea is good. This book will be useful for anyone who has to deal with adverse circumstances. It will appeal to people who prefer anecdotes over reasoning.


He also says we should ignore our feelings and perceptions. While I agree that we should be skeptical of our feelings as they can be unhelpful, we should from time to time at least try to understand where they come from. His approach seems to be to bury our heads in the sand, this seems like the road to toxic masculinity. He likes a bit of good old fashioned male bravado, life is a race and you have to win.
He doesn't take into account simple bad luck and other variables and simply repeats page after page that we need to tackle our problems. We do, but there are other things at play.
For example if our boss asks something unfeasible at work we shouldn't question it, just put our head down and work harder. Working harder seems to be his main tip for a better life, making him sound like Boxer from Animal Farm. Don't question authority or the status quo, just shut up and get on with it. I can imagine what he thinks of protests like BLM.
There are some useful tips however, such as approach obstacles as an opportunity to practice a virtue, such as patience, forgiveness or courage and that we are in control of how we react to our problems. Also we are all guilty of procrastination at times and could benefit from more action. I agree that life is hard and often things contradict themselves. (I'm doing it in this review)
I agree that a degree of anxiety is required in every life but Holiday's approach will have people slitting their wrists and having sky high blood pressure all over the place. He's reinforcing a dog eat dog world where there has to winners and losers. If you're not the next Steve Jobs, cunningly defeating your enemies and taking all the credit, you're a failure and should be ashamed for not working harder. Something Seneca will help us come to terms with a million times better than Holiday.