The Obstacle Is the Way

Maybe this book was overhyped? It's just a collection of anecdotes, some lesser known, some better, some altered to better fit the narrative. I can imagine if you are a gymbro who's never picked up a book before this one can feel like a true revelation.

I don't think moral outrage is the best way to engage with books, but this book is kind of evil.
Some of the advice and insights are useful, but just because a book provides useful advice, it doesn't mean it's good. Holiday's writing is reiterative and derivative, and then he uses so much of the book to praise evil people, using examples of the hardships or challenges they faced and how they used them to their advantage, without any nuance. Maybe the point was that we could learn good things from terrible people, and probably that's where his love for slave master Marcus Aurelius comes from. But maybe I'm giving him too much credit. Two stars.

Hatte starke “tschakka - Du schaffst das”, und “Du musst es nur wollen” Vibes, die die Hustle Culture weiter befeuern.
Wenig Substanz, viel Kalendersprüche.

Key takeaways:

- Perspective is everything. Look at the book from an outside perspective. Ask yourself what your advice would be if it was a stranger going through this same challenge.
- Just because someone says something is awful/hopeless/broken, doesn't mean you have to agree.
- We defeat emotions [control over us] with logic. Logic is questions and statements. With enough of them, we get to root causes which are always easier to deal with.

“We lost money” > “Aren't losses a common part of business?” > “Yes” > “Are these losses catastrophic?” > “Not necessarily” > “So this is not totally unexpected? How could that be so bad? Why are you so worked about about something that is at least occasionally supposed to happen?” > “Well...” > “And not only that, but you've dealt with worse situations. Wouldn't you be better off applying some of that resourcefulness rather than anger?”

An inspiring and approachable call to action. This book found me at the right time in my life, and hope that it spurs the change I am seeking.

This was my review for Holiday's other book ‘Ego is the Enemy':

“At times this book feels largely like a collection of biography book reports and inspirational quotes, but I think the overall lessons contained are vital. Very easy to read, if a bit shallow.”

That about sums this one up as well, frankly.

This book came highly recommended, and had its moments. It wasn't a great fit for me, though.

I'm a Christian, and while much of the advice is logical and can be applied regardless of worldview, the heavy Stoic influence feels... anemic, I guess.

Beyond worldview, I also found it too abstract. I appreciated many of the philosophies in theory, but the application was often nebulous.

It was a slog to finish, and I would have spent the time more profitably reading a blog post on the topic and then moving on to the next book in my to-read pile.

It's a good book and I def recommend you read it. But it falls short here and there with oversimplification and extrapolating stories where there are none. Also did not like the fact that many stories are copy pasted to/from Daily Stoic.

Perhaps not ideal to read cover to cover but a chapter here and there can be very inspiring. What I liked about this book is that it did not try to convince you that there was some key to a better life and you could unlock it with some secret knowledge only the author knew; this book acknowledges that life is hard and really bad things will happen. Actually, Holiday acknowledges that the more success we find the more trials we will pass through. This book is not about avoiding trails, it's about embracing them with stoic wisdom, that was refreshing in what one could consider a “self-help” book.

At first glance I fell prey of availability bias and confirmation bias and my first impression was; this book has nothing new to offer but some generic advice that you could come across any self-help book. This book just like majority of self-help books is containing plenty of famous quotes from well-known people, as well as general advises such as perseverance and persistent for that matter. However I could overcome my biases and start observing what this book has to offer.
Ryan talk about the influence that stoicism had on his life and how revolutionized it has been for him. He explicitly mention that he is not going to talk about stoicism in large and advise the audience to go through the originals such as Meditations by Marcus Aurelius in particular. His aim where illustrating how stoicism comes handy in other famous people life and how stoicism could look like in real life.

The author also talk about perception and how it could be real game-changer in one's life. How great people thrive not in spite of adversity that happened to them but because of it. He quotes Andy Grove (of the founders and the CEO of Intel): “Bad companies are destroyed by crisis, Good companies survive them, Great companies are improved by them”, as well as some other nice examples. Ryan also describes what post-mortem is and how great companies and people use it to their advantage.

I have been through the audio book narrated by Ryan Holiday which ends with nice interview between him and Tim Ferriss. He will talk about his personal life and his profession. Both authors exchange their insights about stoicism and why they are appreciating it.

This was my first contact with the stoic philosophy.

Did not know what to expect, but it was quite an interesting read.

While I found “Ego is the enemy” a bit more well built, this book was really good in forcing you to envision things in a different way, helping you to cope with adversity and obstacles by changing the way you think about them (or see them, or feel them even). While still heavily based on the Stoïc teachings, Ryan Holiday offers a great lot of examples of people overcoming adversity and building something new, better and stronger upon at first seemingly impossible obstacles. Quite inspiring and really helpful for everyone willing to improve himself.

When reading about modern stoicism, this one kept coming up as a book recommendation. The focus is on resiliency and growth mindset when it comes to opposition. This may seem like common advice, but it's sometimes most difficult to remember when in the worst positions.

When reading about modern stoicism, this one kept coming up as a book recommendation. The focus is on resiliency and growth mindset when it comes to opposition. This may seem like common advice, but it's sometimes most difficult to remember when in the worst positions.

Can't say I've ever studied the stoic's before, but I enjoyed the perspective of this book. The bottom line is how you can take anything - good, bad, or ugly - and leverage it for good (even if the “good” is just education of what not to do next time...). While it's not written from a Christian perspective, it is in line with my beliefs that God is quite capable of doing just that on a larger scale (Rom 8:28).

It has made me stop and pause when things don't go my way (even the smallest things) about how I can turn it around to my benefit. It's largely a matter of attitude.

A really good book. Although this book was short it was really dense, I can see myself rereading it in the future and getting a lot more out of it. It was a good introduction to stoic philosophy.

I encourage you to read this book. It's bloody useful. Definitely an upgrade on ones cognition.

There are two reasons I didn't think this book deserved a five star which isn't surprising many people give it. My reasons are pretty basic too.

1. There's simply a lot of fluff. The added stories are relevant and add to his point, but there's still a lot of fluff around what he's trying to get across.

2. it really annoyed me when he talked about Lincoln as he cared about slaves. There were several other passages about famous people (or notorious as Lincoln is more aptly described) that I also didn't agree with. Lincoln was one of the most hated presidents ever during his time.

“I will say then that I am not, nor ever have been in favor of bringing about in anyway the social and political equality of the white and black races - that I am not nor ever have been in favor of making voters or jurors of negroes, nor of qualifying them to hold office, nor to intermarry with white people; and I will say in addition to this that there is a physical difference between the white and black races which I believed will forever forbid the two races living together on terms of social and political equality.”

- Lincoln during his fourth debate with Stephan Douglas - Sept. 18, 1858



That said, the actual material itself and the lessons are worth five stars.

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.