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Book Summary: The Obstacle is the Way by Ryan Holiday

  • Terry
  • July 12, 2020
  • 7 minute read

This is a book about facing challenges with the right mindset and attitude

This is a book about facing challenges with the right mindset and attitude
4 5 0 1
I love books that introduce us to ways that allow us to master our minds, and The Obstacle is the Way totally fits the bill. It is a guide on how to re-frame your perspectives and manage your expectations when dealing with challenges in your life. The concepts introduced are also almost immediately applicable, which is something that I appreciate about personal development books. The chapters are relatively short and concise, making it a very pleasant read especially if you’re the type that don’t like to stop reading in the middle of a chapter. Overall a great book for anyone looking to improve the way that they deal with obstacles.
I love books that introduce us to ways that allow us to master our minds, and The Obstacle is the Way totally fits the bill. It is a guide on how to re-frame your perspectives and manage your expectations when dealing with challenges in your life. The concepts introduced are also almost immediately applicable, which is something that I appreciate about personal development books. The chapters are relatively short and concise, making it a very pleasant read especially if you’re the type that don’t like to stop reading in the middle of a chapter. Overall a great book for anyone looking to improve the way that they deal with obstacles.
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The Obstacle Is The Way by Ryan Holiday

To be frank, I got this book as an “impulse buy”. With so many praises for Ryan Holiday’s works on my social media feeds, I thought I’ll give it a shot. Looking back, I was quite happy with that snap decision! The central idea for this book is about reframing our perceptions of obstacles in our lives; how we can motivate ourselves to take action and overcome them with a simple mindset tweak. There are so many takeaways from this book, and I can’t wait for you to read about them below!

Obstacles are opportunities to learn and improve ourselves

“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition”

If I were to condense the essence of the entire book into one line, it will be the quote above. This is not completely new – I’d even say it is borderline cliché – but it captures the main idea very clearly; that there is always something to learn from any challenge we face.

When we encounter things that we are unfamiliar with, it usually becomes an obstacle that stops us in our tracks. Sometimes, these obstacles appear to be impossible to overcome, and might even instil a sense of uncertainty among us. However, challenges like this can highlight an area of our lives that we could learn more about and improve upon. This is what Ryan Holiday wants to tell us in this book – that the obstacle does not lead us away from the path; it IS the way forward in our path.

The disciplines of overcoming obstacles

According to Ryan Holiday, the process of overcoming obstacles consist of three key principles, which he calls “Disciplines”:

  1. Perception: This is all about the way we see the obstacle in our mind’s eye, and how it influences our attitude and approach towards it.
  2. Action: This deals with the way we use our energy and creativity to break down a seemingly large obstacle into smaller, more manageable parts. It also determines how we transform such challenges into opportunities for growth.
  3. Will: How we come to terms with the reality of the situation and built it into our identity forms the basis of the third and last discipline.

Part I – Perception

“… through our perception of events, we are complicit in the creation – as well as destruction – of every one of our obstacles.”

Our perceptions of obstacles determine how feel about them. As Holiday shares, “desperation, despair, fear, powerlessness – these reactions are functions of our perceptions”. He also later added that fears “are bred mostly from unfamiliarity”. Indeed, when we perceive a challenge to be insurmountable, we might feel disheartened, helpless and overwhelmed about it. This is where many might turn away, give up or settle for something less.

In Take Control Of Your Life, Mel Robbins shared that instead of running away from our fears, we should run towards it instead. This is because our fears point to an area of our lives that we do not know much about. By improving our knowledge and understanding in this area, the fear and uncertainty will be replaced by logic and authority. In turn, this helps us to overcome our obstacles and stay the course towards our goals. Similarly, Holiday echoes this by saying that with knowledge comes the clarity and strength to overcome these challenges. Just because we don’t have the degree of competency needed to resolve it now does not mean it is impossible. By reframing it this way, we flip the obstacles upside down where it become avenues of self-improvement.

Having the right perception also helps us discern between things that are within our control and those that are not. This is important because “focusing exclusively on what is in our power magnifies and enhances our power. But every ounce of energy directed at things we can’t actually influence is wasted”. Therefore, we’ll want to concentrate our efforts on areas with the most impact so we don’t waste valuable time and energy.

Part II – Action

“Excellence is a matter of steps. Excelling at this one, then that one, and then the one after that.”

The next principle of Action exerts that effective action is a directed one; with the right perception, the next thing that matters is what we do in response to what has occurred. Then, to sustain it, we’ll need momentum. Momentum is generated as long as we get started and take the first step.

Just get started; get moving!

There seem to be two types of people in this world; some jump right into the action, while others tend to ponder more before doing so. I identify more with the latter; sometimes, I feel like I might even be overthinking things. However, Holiday reminds us that “the world does wait for us”. The more we think, the more our minds come up with excuses to not do it. This, in turn, gives the impression that the obstacles are bigger than what they appear to be.

To overcome this, it’s always good to just get started. And when we’ve taken the first step, don’t stop, and keep going relentlessly. Where there are options available, there should be action. Only when all options are exhausted do we then turn to innovation; this is where we find new obstacles, which we will then find new ways of doing things. “Doing new things invariably means obstacles.” says Holiday, “A new path is, by definition, uncleared”. Only when we persist in our efforts can we then learn the vital lessons contained within.

Fail forward every day

To help guide our actions, we can turn to our where we fail. Failure acts as a signpost to tell us what’s working and what isn’t, highlighting areas that need more work. After every setback, we should ask ourselves, “what went wrong here? What can be better? What am I missing?” This is how reflection and introspection helps us to learn from our mistakes and learn to do things differently until we overcome our obstacles.

In a previous post, we saw that tiny gains sustained every day can lead to great results over time. Popularised by James Clear, the same principle applies to managing our obstacles. We don’t always need big action; smaller ones that are done well every day works just as well. A former director at my workplace used to celebrate small wins by exclaiming, in a sassy Auzzie accent, “NAILED IT!” It didn’t seem much, but it stuck and reminds me time and time again that we want to always nail the present – do the work today, and look forward to it tomorrow. Soon enough, we realise that that challenge wasn’t so bad after all, and quickly put it behind us.

Actions should also be flexible and pragmatic

“Force can’t try to match force.”

Warren Buffett once said that “[a] philosophy should supply guidance but not rigidity.” The same is true when we try to overcome our obstacles. In solving problems, flexibility and pragmatism is crucial. Sometimes, it might be more prudent to go around the obstacle instead of facing it head-on. Holiday suggests that approaching obstacles from a “line of least expectation” helps to avoid direct confrontation and lengthy battles.

Holiday also shares another interesting perspective: that some bigger challenges eventually get rid of themselves. In other words, the best course of action is inaction, and have the patience to wait out the storm. People who are uncomfortable with doing nothing might not agree with this, but I thought it was a very unexpected and fresh point-of-view.

Part III – Will

While the right perception helps us manage how we feel about obstacles, and the right actions help to resolve it, it is the strength of will that grants us the mental endurance needed to pull through the work and overcome our challenges. Willpower is like a muscle, and has to be actively trained up over time. The more tension and discomfort we feel in working through our obstacles, the more it helps us build our strength. Just like an arc, the way to strengthen it is to put weight on it; only with tension does it bear weight.

Willpower can be likened to perseverance, and I thought that it can be used interchangeably with persistence. However, Holiday explains that they are different; Persistence gives us the strength to hammer a problem until it breaks, but perseverance is what helps us work through a long line of problems that crop up along the way, enduring setback after setback. Holiday also draws a great analogy of this to a cat – when they fall, they always fall on their feet.

Closing thoughts

Life is a never-ending series of challenges, with the next one better than the last. The three disciplines shared by Ryan Holiday serves to remind us that every obstacle is an opportunity for growth; with each challenge overcome, we get better. You can even say that we improve because of the obstacles.

“Vires acquirit eundo”

“we gather strength as we go”, latin saying

In closing, The Obstacle is the Way teaches us that with the right perception, intentional and direction action, and a strong will to endure and accept the world for what it is, we will have the tools to flip any obstacle on its back. Instead of turning away from it, we use it to guide us onto a new path, for the obstacle becomes the way.

Share your thoughts with me!

If you’ve read The Obstacle is the Way by Ryan Holiday, I’d love to hear your thoughts on it. Drop a comment below, or share this post with your friends with the tag @kopi.thoughts!

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  • Mindset
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Terry

A kopi-enthusiast and gin-lover, Terry spends his time reading up on personal development & investment, connecting and sharing ideas with people and looking out for opportunities to collaborate on the next side hustle.

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