Hi! Recently, I read The Obstacle Is The Way (TOITW) by Ryan Holiday. Here’s my take on it:

In his book, Ryan Holiday uses Stoic techniques to show the method of turning obstacles into springboards for the future. He uses several examples and anecdotes of famous people to explain how they all overcame obstacles. Ryan points out that they all used three common techniques: perception, action, and will. I’ll break this down for you using a common example: losing money. Let’s say that I have lost a million dollars on a startup that has crashed. Obviously, I’m very down, but I have to overcome this problem. But fear not, because I have read TOITW and know exactly what to do. So, what is that?


Well, the first technique that Ryan recommends is changing our perception of the challenge that we are facing. He’s not talking about glass-half-empty versus glass-half-full here. He is talking about a complete change in perception. Here’s an example, using my startup scenario from earlier:

Glass-half-empty versus glass-half-full would mean looking at the brighter side of the problem and thinking along the lines of ‘Hey, I lost a lot of money here’. But no problem, because I have experience and can find a higher-paying job if I sell my company! This doesn’t solve the problem, nor does it find a way to get around it. In fact, this approach simply gives up on the startup and looks for a way to make the problem seem a bit better. But what you should think in this example is I lost money, not my arm. It could be worse. 

After you tell yourself that, you need to start thinking about how to bounce right back. You need to think – Why did I fail? How can I fix this? Not – Well, I failed, I give up. 

A great example from the book is an anecdote about General Ulysses S. Grant in the American Civil War. General Grant was tasked with taking the city of Vicksburg, which was a prominent riverside Confederate city. He besieged Vicksburg and looked at several possible weaknesses of Vicksburg before developing a plan. This is the attitude that we need to maintain.


The second technique that Ryan suggests is acting on the information that we have received through changing our perception. He mentions that while planning is important, sometimes we plan far too much and forget to act. Ryan mentions just how important that last piece is: we have to act. Continuing with the example of General Grant, we see that the general was a man of action. He planned several methods of invading Vicksburg. He tried methods for a substantial amount of time as the press chewed him out for his failures. Finally, though, one of his ideas clicked, and he successfully invaded the city of Vicksburg. This is something that we need to learn – to act.

This is not saying that planning is useless. Perception is the first step of the process, and after we receive new perspectives, we need to make a plan. And – here comes the important part – we need to act on that plan. If it fails, we need to create a new plan and try that out. Going anywhere without a plan is foolishness. Planning too much without taking action is also foolish. Of course, the latter is preferable to the former, but not by too much. Part of the mottos that we tell ourselves should be Action, action, action. Inertia is unavoidable if we don’t tell ourselves to be confident and act upon our plan.


The last step of Ryan’s process is will. This step actually has less to do with mental toughness and more to do with surrendering to a higher power (“God’s will”). Let me explain using an example. General Eisenhower wrote a letter to his wife stating that he had done the best that he could, his troops were fit and enthusiastic, and the rest was in the hands of God. This is the difficult truth of life: we only have control over so much. Stressing over the things that we don’t have control over will lead to nothing but lots of difficulties and undue stress for us.

I too am guilty of stressing unnecessarily, especially in the days after turning in an exam. This is a pointless worry. The examination won’t alter its results based on my level of stress. But I may perform poorly on other exams due to my stress, and my stress will chip away at my willpower. What has happened is over and cannot be changed. Stressing over it is pointless. Rather, the solution is to restart the cycle and perceive things differently to see the good in the situation.


This book is recommended to everybody. That’s right. Every single person in the world can benefit from Ryan Holiday’s Stoic teachings. This book will, of course, help entrepreneurs without a doubt. But it will also help anybody who has to face obstacles in their life (everybody).

Highly recommended, great book!

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Rishi Sridhar

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