Posted in Book Review

Book Summary + Opinions: ‘The Obstacle Is The Way’ by Ryan Holiday

I actually wrote this last year after reading the book, but seeing Tim Ferriss recommend it again in his newsletter made me decide to share this:

The Obstacle Is The Way is a collection of stories and principles about Stoicism, a philosophy I stumbled upon last year and I’ve found very helpful, thanks to books like this and authors like Ryan Holiday who also wrote The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living.

So without further ado, let’s get into this.


The Celts have a legend that says, just before a person is born they are allowed to choose every hardship that they would experience during their life time. Every challenge a person chooses is one they would be able to overcome and would push them to learn and grow but would not defeat them.

The Christians believe that they would never face any temptation they wouldn’t be able to bear and stand against, but that God would with every temptation provide a way of escape.

These two beliefs provide a fundamental way humans are supposed to view challenges and obstacles in their way in life. They are meant to give the believer a hope that transcends earthly power, a sense of control and domination over every challenge humans could possibly encounter.

The idea is so fundamental that it has over time pushed the necessary will and grit that we humans naturally possess to the surface when we need it. It tells us that something beyond us is in control, someone’s watching out for us and with whom we cannot fail, because they’ve got our back-be it God or ourselves.

Obstacles are mostly seen as a thing that is meant to destroy and beat us face down into the ground because it was placed ahead of you for that very purpose. But what these beliefs do is take back control from the unknown force that we would so eagerly believe is out to get us and see us fail and give it back to us because there is no way we would design failure ahead of ourselves, or like the Christians attribute power of the challenge to God, because God would never in his loving kindness design failure for us.

The essence of this is the very first step to overcoming obstacles and challenges. It is understanding the challenge. It is about your perception, how you see the obstacle before you. If you believe something is out to get you, every corner you look, you’ll probably find closed doors and a sign that whatever it is that’s after you is closing in on you. That is what the confirmation bias tells us. We see confirmation to support an already existing belief in new experiences.

To overcome challenges, the old mindset first need to be ditched. We have to turn away from the belief that obstacles are designed to make us fail or to run us into the ground or to stop our progress.

Ryan Holiday in his book, The Obstacle is The Way explained three things we need to turn obstacles into propellant: Perception, Action and Will.


Every obstacle is an opportunity to push your limit further back. To overcome challenges, they must first be understood, then can you know how best to tackle it. While every challenge may be somewhat unique in the form it presents itself in our lives, they all serve the same purpose: to bring out the best in us. To make us realise the strength we have up to this point is not our best yet, we can go further, we are stronger than we know, we can overcome yet another challenge or obstacle in our path.

When we understand this, we begin to see challenges as stepping stones rather than stumbling blocks. Then we can proceed forward through unpleasantness with persistence and perseverance.

John D Rockefeller once said, “oh, how blessed young men are who have to struggle for a foundation and beginning in life.
This is a man who had faced many obstacles in his life and had understood them, thereby his perception of obstacles changed and he saw them as what makes us rather than destroys us.
Oprah Winfrey went through what most women cannot even bare imagining and she allowed it to shape her into the strong powerful woman she is today, who serves as a source of motivation to the world.

In reality, things are just the way they are, we are the ones that interpret it as good or bad. Someone may see an occurrence as a needed push, or the lesson he needed to learn for further down the road, while another may see it as the bus stop of their ambition.

Perception is powerful and a change in the old fixed mindset is important.

Stephen R Covey in 7 Habits of Highly Effective People called it a paradigm shift.

We all view the world from our own personal binocular which is made from our life experiences and encounters. What paradigm shifting says is that we need to abandon that binocular and begin to view the world the way it really is, we need to start being objective and strip things of their cover and call them the way they really are because perspective is really everything; every other thing builds on it.

What next?


When we have correctly seen the way an obstacle is and we understand its real purpose, then what? Do we just run headlong into the mountain ahead of us?

No, we need focus to proceed. Every distraction on our way must be done away with. Our undertaking is one that will shape our lives, we cannot allow ourselves to be distracted neither must we allow ourselves to be overwhelmed by the supposed immensity of the obstacle. We need to proceed with focus, taking every step one after the other. We need to live in the moment, tackle the challenge right in the present. We realise we can only deal with the present so we steel ourselves for this. Then can we begin to act.

Understanding is the first step. The second crucial step, as important as perception is action. Nothing can replace ‘doing’ after as much planning as we can make. Execution is what brings all the planning to life and that is what counts, that’s real life, a general can plan for a battle in his tent, but the soldiers have to get out on the battle field and execute it. That’s what we do-we do, we act.

When we act, then can we know where we are weak, where more strength is needed, where more tactic and more ammunition should be deployed. We make mistakes and then we learn from it. Failures are not the end of the way, rather they show us the way by showing us what isn’t the way.

Remember Thomas Edison? He made 1,000 unsuccessful attempts at inventing the light bulb. When a reporter asked, “How did it feel to fail 1,000 times?” Edison replied, “I didn’t fail 1,000 times. The light bulb was an invention with 1,000 steps.”

No matter how many wrong ways we have to find before finding the right way, what is important is that we keep moving. We keep going through the unpleasantness, because the failures are all part of the story. They are a sign that you are trying.

Like earlier said, moving against an enormous obstacle can become overwhelming, so it is important to go a step at a time, break the task ahead of you into components and tackle them one by one. Everything is made up of little pieces, we just need to find a way to dismantle it piece by piece.

We shouldn’t be strict to one process, though. The result should be the focus. Any right way is the right way. It doesn’t matter if you go about solving a problem through a different way than someone else, as long as it is not illegal and you keep your view objective, it is the right way you need to go about it, period.

The way that works for you is the right way.

However, one of the major impediments of action is the lie we tell ourselves that we are not fully equipped, so we cannot go forward until we get this or that. We say it is because there is no money, so we can’t do anything about our dreams. Or we say there is no opportunity, we have to wait for opportunity to come our way or for someone to present us with an opportunity.

In reality, there is rarely a time we are totally unable to do anything. Yes, you don’t have everything you need, but you have something, you always have something to work with, and what you’ve got is more than enough to go make a meaningful move in the right direction. You take what you have and use it. Don’t wait. Make do with what you’ve got.

Sometimes, we come across obstacles that no matter how hard we push against it, it just won’t budge. These are times when we use the obstacle to take us to where we want to go. instead of getting it out of the way, maybe all we need to do is climb over it or go around it. In cases like this, the obstacle can be harnessed in a way that serves us.

That’s one way. The other way is it provides us with the opportunity to explore other paths that will lead to the destination. Sometimes, we have to go back and try a different route. That’s being smart. We don’t have to stick to something that is obviously not working for us, we can use that opportunity to review why we want that thing in the first place. If our motive for going that way is still on track, then that’s what matters, we will definitely find a new way of going that takes us to what we want.

Another way is to let the obstacle counter itself. Certain obstacles can work against themselves. In such a time. the best form of action is non-action. The best thing is to stand still and let the obstacle fizzle out. It is a temporary delay on our way. Fine. Don’t waste your energy trying to force it out of your way or try climbing it because it is temporary. Wait, let it go

Chemical reactions require catalysts to react faster just like our body needs enzymes. Also, certain long time ideas we’ve been harbouring need the right catalyst to execute. Obstacles can serve as accelerators to those kinds of events, they provide the right time for execution.

You see a challenge and take it as the best time to do something that needs to be done. Obstacles can do this when a challenge comes our way that seems to making things head in a negative direction. We can pick such a challenge and re-frame it in a way that it works in the positive for us. Like a vector has a negative, just heading in the opposite direction, an obstacle might come heading in the negative, threatening to ruin everything we’ve walked so hard to build. If we see that as an opportunity to strengthen a weak point in our defence, we can harness the negative force to work in the positive for us.

And finally…


We make plans the way we expect things to go. In reality, outside forces will work against our plans. And most of those forces, we have no control over, so it is important that as we plan our lives, we expect our plan to not work, we expect it to fail. It will help us have alternatives. Moving without a backup will sometimes cause us to be stuck as life brings obstacles we can do nothing about our way.

Sometimes no amount of planning, no amount of thinking-no matter how hard we try or  persist – will change the fact that some things just aren’t going to work. Being prepared for this helps us know how to better manage such a situation when we are faced with it. Not every obstacle is surmountable. But we only accept this after trying everything within our power. But that doesn’t mean we can then give up. Rather we should allow it to strengthen us for what else we will need to face. We allow it build our fortitude.

And that’s our will.

No matter what we are going through, no matter what we have to endure, we should be able to find a greater a purpose greater than ourselves. That purpose will help us endure and handle it with firmness and forbearance.

A strong will must be coupled with the right perception and action.

Will helps us derive meaning from the obstacles we cannot simply overcome. It helps us make the best of a terrible situation that we tried to prevent but couldn’t, it helps to deal with fate with cheerfulness and compassion.

That’s the point of a greater purpose outside of ourselves. It gives us the ability to be able to feel compassion for others other than ourselves.

And sometimes the only answer to “what if…” is that, “it will suck but we’ll be okay.”

The practice of premeditation of evil helps us prepare for things that can fuck our plans up and prepare ourselves against it. Or, equally important, for those that can’t be prepared against, we prepare ourselves for it.

It helps us manage our expectations. It helps us accept a detour we can’t change and quickly open to taking the alternate route.

Amor fati.

When we focus on helping others, we focus on the greater purpose than ourselves, our own personal fears diminish because we are not focusing on it, which is what fears need to strive; the more we think about them, the larger they get. But when we shift our focus to something outside of ourselves, to something bigger than us, the fears diminish.

Think about helping others and go ahead with helping them because in so doing, you’re also helping yourself. Nothing-no obstacle or challenge we are going through should interfere with our empathy towards others. Instead help others survive and thrive. Be strong for others. It will make you stronger.

Premeditate your end, keep in mind that you are mortal and it will all soon end.

The more you accomplish, the more things will stand in your way, there are other staggering mountains after the one before you now. Let overcoming this one build your fortitude to overcome the next one and the next one after that.

Remember: where the obstacle is, is the way you need to go.

6 thoughts on “Book Summary + Opinions: ‘The Obstacle Is The Way’ by Ryan Holiday

  1. Obstacle is the Way is one of my favourite books. It opened up Stoicism for me which has been a life changer. This is a great write-up. Thanks for sharing. I have been recommending this book to a lot of my friends and have recommended on my site too: check it out, I think you might enjoy it if you liked Obstacle is the Way.

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