---
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title: "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

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The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph [Holiday, Ryan] on desertcart.com. *FREE* shipping on qualifying offers. The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

Review: Excellent update - The Obstacle Is the Way is pithy and genuinely impressive. It’s the kind book worth revisiting every six months or so just to reset your mindset and remind yourself of what matters. Ryan’s style really shines here. He takes a simple subject, finds a relatable example, and then delivers a short, sharp insight on why it matters. It’s efficient, thoughtful, and easy to digest. Honestly, I’m curious what the “30-minute summary” version of this book looks like, because the original already feels like one: quick, smart, and packed with useful takeaways.
Review: Ryan Holiday? Great book if you want to learn. Not a book for people who believe in "The Secret". - While I know Ryan personally, I believe that I am uniquely qualified to review this book and, after reading a lot of the comments, add to the discussion. A lot of people miss that Ryan is articulating a journey and is translating it into something edible and powerful. Something 99% of us at ANY age cannot do, even with "wisdom of experience". 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..

## Technical Specifications

| Specification | Value |
|---------------|-------|
| Best Sellers Rank | #56,772 in Books ( See Top 100 in Books ) #6 in Motivational Management & Leadership #9 in Business Motivation & Self-Improvement (Books) #23 in Success Self-Help |
| Customer Reviews | 4.7 4.7 out of 5 stars (5,677) |
| Dimensions  | 5.25 x 0.87 x 7.27 inches |
| Edition  | 1st |
| ISBN-10  | 1591846358 |
| ISBN-13  | 978-1591846352 |
| Item Weight  | 2.31 pounds |
| Language  | English |
| Print length  | 224 pages |
| Publication date  | May 1, 2014 |
| Publisher  | Portfolio |

## Images

![The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph - Image 1](https://m.media-amazon.com/images/I/31pwp+oPiXL.jpg)
![The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph - Image 2](https://m.media-amazon.com/images/I/41qkPXBugXL.jpg)
![The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph - Image 3](https://m.media-amazon.com/images/I/61EYR-vwUlL.jpg)
![The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph - Image 4](https://m.media-amazon.com/images/I/71Tze+xZcgL.jpg)

## Customer Reviews

### ⭐⭐⭐⭐⭐ Excellent update
*by J***Y on November 14, 2025*

The Obstacle Is the Way is pithy and genuinely impressive. It’s the kind book worth revisiting every six months or so just to reset your mindset and remind yourself of what matters. Ryan’s style really shines here. He takes a simple subject, finds a relatable example, and then delivers a short, sharp insight on why it matters. It’s efficient, thoughtful, and easy to digest. Honestly, I’m curious what the “30-minute summary” version of this book looks like, because the original already feels like one: quick, smart, and packed with useful takeaways.

### ⭐⭐⭐⭐⭐ Ryan Holiday? Great book if you want to learn. Not a book for people who believe in "The Secret".
*by C***G on May 25, 2014*

While I know Ryan personally, I believe that I am uniquely qualified to review this book and, after reading a lot of the comments, add to the discussion. A lot of people miss that Ryan is articulating a journey and is translating it into something edible and powerful. Something 99% of us at ANY age cannot do, even with "wisdom of experience". 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..

### ⭐⭐⭐⭐⭐ A very good read that will offer new helpful perspectives!
*by H***G on November 12, 2025*

I am really a huge fan of Ryan Holiday and his books always carry a wisdom that resonates, especially as much of his writings are based in ancient stoicism. He writes in a very relatable way that also helps you see a different perspective, which in my book is always welcomed. This is my second purchase of this book as I gave a copy to friend who absolutely loves this book!

## Frequently Bought Together

- The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph
- The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living
- Stillness Is the Key

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*Product available on Desertcart Senegal*
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*Last updated: 2026-01-31*