The obstacle is the way by Ryan Holiday is shallow and uninspiring

Luca Franceschini
7 min readSep 14, 2022


14 September 2022

TL, DR: 🤨😠📕🗑️

I recently got The obstacle is the way by Ryan Holiday, and it was awful. The book is about how to overcome difficulties by embracing them. While some ideas are good, the narrative on how to act on them is flawed.

The book is divided in three parts, which can be summarized as:

  1. Perception Try to see obstacles as opportunities. Alter your perception to stay in control of your emotions. Focus on what you can do. (61 pages)
  2. Action Act, have discipline, be persistent. (62 pages)
  3. Will Develop will power. It must be built up over time to be available when needed. (57 pages)

The main ideas are easy to phrase and difficult to practice. How to act on the ideas would be the interesting part, which Holiday fails to present. The book is filled with cherry-picked twisted stories (mostly about white men) which might seem inspiring, but are unrelatable.

Survivorship bias everywhere

Survivorship bias occurs when only available information is considered and the rest is discarded. E.g.: consider only successful businesses, whatever they did is good, with the implicit assumption that none of the unsuccessful businesses did the same. The result is a tautology:

  • successful business are successful because they make successful decisions,
  • successful businesses make successful decisions because they are successful.

This is a damaging idea when applied as a personal mindset. If you don’t succeed at what you want, it’s because you don’t have the right mindset / skill / willpower. There is no room for a growth mindset, either you have the guts or you don’t.

The truth is that sometimes you can do everything right and still fail. While Holiday dedicates some sections about recognizing failure as an acceptable outcome, most examples are phrased as the great white man leading with the right choice at the right time.

George Clooney The world of acting is brutal: there are many more aspiring actors than available acting careers. Even the best actors might need years for their breakthrough, if it ever comes. As other actors, George Clooney failed many auditions before thriving. According to Holiday, “a new perspective” was all he needed to be considered. After he embraced the “new perspective”, everything started working magically.

This is a simplistic view with a circular logic. Failing auditions is because the perspective is wrong, succeeding auditions is because the perspective is right. The perspective at the time of a successful audition is the right one, all the other times is wrong.

No matter which perspective was actually used by Clooney, that could have never been enough. He still needed to stick to the auditions when not considered. He still needed to act good. But apparently, actors who don’t make it just miss the right “perspective”.

Business founded during financial downturns Holiday lists a bunch of businesses founded during financial downturns, like Microsoft (recession in 1973–1975) and LinkedIn (2002, post dot come bubble). According to him:

[…] these businesses had little awareness they were in some historically significant depression. Why? Because the founders were too busy existing in the present — actually dealing with the situation at hand. […]”.

Here is the circular logic again:

  • businesses thrive, therefore their founders are “busy existing in the present”,
  • the founders are “busy existing in the present”, therefore their businesses thrive.

By definition a financial downturn affects the entire economy. Businesses must carry some entrepreneurial risk and some of them will go bankrupt no matter what.

Are all bankruptcies now because of founders not “busy existing in the present”? Apparently the New Deal was unnecessary. Franklin Delano Roosevelt could have saved a bunch of taxpayers’ money by inspiring Americans to be “busy existing in the present”.

World war two Apparently the right perception also allows you to win battles.

In the weeks and months after the successful invasion of Normandy by Allied forces, they faced [the blitzkrieg] again: a set of massive German counteroffensives. How could they stop it?

According to Holiday, only the American General Dwight D. Eisenhower “answered that question”. Every other Allied force was just standing there without contributing to the discussion.

[…] Eisenhower was able to see the tactical solution that had been in front of them the entire time: […] the Nazi strategy carried its own destruction within itself. Only then were the Allies able to see the opportunity inside the obstacle rather than simply the obstacle that threatened them.

Forget that the Germans were losing since the battle of Stalingrad. Eisenhower’s perspective won the war.

Where was the “opportunity inside the obstacle” at the battle of Monte Cassino, when the Allies faced many more causalities than the Nazis? Was Eisenhower at the bathroom when the Monte Cassino monastery was flattened by U.S. bombers? Maybe that time just the Germans saw the “opportunity inside the obstacle”.

Even by taking this narrative at face value, how is it supposed to be useful? If it were that easy to see the “opportunity inside the obstacle”, this and several other books wouldn’t exist in the first place.

Taking example from the wrong people

Steve Jobs Every business book has to claim that Steve Jobs was a genius and everything Apple does is great. Holiday consequently includes a chapter titled Think Differently.

[…] in the design stages for a new mouse for an early Apple product, Jobs had high expectations. He wanted it to move fluidly in any direction, […] but a lead engineer was told by one of his designers that this would be commercially impossible. […] The next day, […] Steve Jobs had fired the employee who’d said that.

I’m fine praising Steve Jobs’ entrepreneurship, he was definitely a smart man. Still, that does not mean everything he did was right. In this instance, Steve Jobs was an asshole.

The designer must have had his reasons to claim the commercial unfeasibility of the mouse. Steve Jobs could have improved his perspective by talking to the designer. He could have tried to understand his reasons, allow him to challenge his assumptions and grow. Instead he just replaced him with a yes man. If an employee is supposed to have the right perspective, why does not the same apply to who’s in charge?

This is a double standard: the complaining employee is wrong, the complaining boss is right. A toxic work culture does not mean the boss is a visionary.

Erwin Rommel The worst part of the book is the Rommel myth shown as a positive example. Holiday’s narrative looks like Nazi propaganda:

[German Field Marshal General Erwin Rommel] saw war as a game. A dangerous, reckless, untidy, fast-paced game. And, most important, he took to this game with incredible energy and was perennially pushing his troops forward.

The German troops has a saying about him: Where Rommel is, there is the front.

That’s the next steps: ramming your feet into the stirrups an really going for it.

And worse:

Rommel knew from history that those who attack problem and life with the most initiative and energy usually win. He was always pushing ahead, keeping the stampede on the more cautious British forces to devastating effect.

And again, in another chapter:

Rommel, for instance, was renowned for his Frontierfahrung, his sixth sense for the decisive point in battle. He had an acute ability to feel-even in the heat of the moment-the precise instance when going on the offensive would be the most effective. It’s what allowed him to, repeatedly and often unbelievably, snatch victory from the jaws of defeat.

Bundesarchiv, Bild 146–1977–119–08 / CC-BY-SA 3.0

There is a part where Holiday recontextualizes the myth, by claiming that Rommel’s victories were actually part of the Allied strategy:

Remember Erwin Rommel and the quick work he made of the British and American forces in North Africa? There is another part to that story. The Allied forces actually choose that disadvantageous battlefield on purpose. Churchill knew that they would have to take their first stand against the German somewhere, but to do that and lose in Europe would be disastrous for morale.

In North Africa, the British learned how to fight the Germans-and early on they learned mostly by failure. But that was acceptable, because they’d anticipated a learning curve and planned for it. […]

This is not enough. You can’t just praise a Nazi general by pretending the Allies were outsmarting him the whole time.

If the book had just contained unhelpful examples, I would have forgotten it like many others. When reading Rommel’s praise, I knew I was going to write this blog post. I can’t keep my opinion to myself after reading such a steaming pile of bullshit.


I don’t recommend The obstacle is the way. Not even skimming through can be useful, the few valuable ideas are too simple and too sparse to stick.

On a related topic I can instead recommend Atomic Habits, by James Clear. Unlike The obstacle is the way, Atomic Habits provides a useful framework on how to build up over time the kind of grit that allows you to overcome obstacles.

I can also recommend another book by Ryan Holiday: Conspiracy. Instead of dozens of useless examples, it is one good real story of Peter Thiel’s plot to take down Gawker.

Originally published at on September 14, 2022.