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Key Insights from The Obstacle is The way by Ryan Holiday

Hey There, Welcome back to this space where you can dive into some inspiring books! On the occasion of Ganesh Chaturthi, I hope lord Ganesha shine his light on all of us so that we can turn our trials into triumph and overcome any obstacles that comes in our way!

Do you face obstacles and difficulties in your life? Would you like to know how to overcome those difficulties? Irrespective of what is your background or what are your goals, facing difficulties is inevitable part of life. Whether mental, physical or emotional we all regularly feel stretched from many sides and find many obstacles in our way. We might sometimes find us paralyzed by these barriers and often procrastinate trying to avoid confronting them. However, what if these obstacles actually presented an opportunity to move forward. In fact, what if we could use these obstacles to our advantage. Well sounds utopian…right! Nevertheless, this is the key argument that author Ryan Holiday, present in his best -selling book “The Obstacle Is The Way”. By the virtue of this blog I tried to distil my learnings and highlight from this book as it elaborates the timeless art of turning adversity to advantage which is very insightful and intriguing!

Author Ryan Holiday draws some of the principles from Stoicism which is the School of Greek Philosophy that shares very powerful principles and life lessons. Ryan also leverages lots of stories from history to ultimately make the point that we are bound to come across obstacles at every stage of our lives. Normally, we want to avoid it, form some kind of escape mechanisms like switching to something else. However, instead of running away from them we need to learn the art to tackles them. This process of overcoming obstacles can not only help us reach our destination but also ultimately shape us to live a happier and more productive life. This art of tackling complex and hairy problems is vividly described in this book. What I like most is that it is very well written in form of parts, you can read it all at once or like me part by part! When we put all the parts together it make a triad of three interdependent steps that is Perception (Mind), Action (Body) and Will (Heart) that can help us emerge stronger.

Key Insight 1 – Perception

First part of the book talks about discipline of the Perception. How we see and understand the events around us makes all the difference! I believe, more importantly how we decide to judge and interpret those events actually shapes everything else in life. Just think about it, our perceptions can be either source of strength or they can weaken us. I know there are incidents when we suffer because of external conditions however, if we are emotional, subjective and short-sighted we will interpret an event badly leading to unhelpful perceptions. While if we control our emotions and put things in prospective such that we are examining things objectively then we can begin to see obstacles with greater clarity. From this section, key takeaway that I gauge from the book is power of perception. It’s not the things that upset us it’s our opinion about things that causes pain and hurt. Essentially, how we view things determines what we are going to do with what has happened to us.

“Perceiving Eye sees more than it is there

The Observing eye sees only what is there”

As Dumbledore famously once said nothing is good or bad but thinking makes it so! You see it’s natural to feel frustrated, angry and scared as things don’t go our way. Ryan says we can either let these primal negative feeling control our response and choose to give in to them. Or we can learn to filter them and detach ourselves from situation thereby looking at things bit more objectively.

Key Takeaway 2 – Action

Second part of the book talks about discipline of the Body which is how we respond to the external stimuli. Indeed, our life is diabolic of our thoughts but our life is also about choices we make and actions we take. Great German philosopher Friedrich Nietzsche once said my formula for greatness in a human being is “Amor Fati”. What it essentially means is one wants nothing to be different, not forward, not backward, not in all eternity to not merely bear what is necessary still less conceal it but to love it in. Amor Fati attitude is more in line with an ancient stoic mindset that stays unaffected by the events. They are cheerful in the face of any event whether it is positive or negative.

Simple yet concrete way to practice in Amor Fati attitude is to see your so-called negative emotions as an assets. If you are feeling that people fear disruptions, it is good because it is example that your actions is driving some kind of innovation that is shackling the rust of comfort and convince. I have even highlighted this part in my book since it really resonate with me. But the bigger question is how we can all cultivate the skill to cultivate positive emotions from series of unfortunate events. Author Ryan Holiday gives another way to harness the positive energy is by breaking negative emotions with logic. The first thought should not be I am not okay with this or I think that is enough. Rather completely reverse your feeling to “I feel Great about this”. This is because if it has happened then it was meant to happen and we should be glad that it did happen. The bigger picture should be I need to make the best of it! I know it’s difficult but we got to try…

Key Insight 3 – Will

Third part of the book talks about power of Will. Well, whether you like it or not, life will kick your ass, break your heart and through things at you that you cannot solve. What is demanded of you in these situations is endurance and perseverance. Let me explain you with the example Ryan gives in his book. He uses the story of boxer Jack Jonson to perfectly illustrate in “Amor Fati” attitude. So Ryan takes us back to 4th July 1910, when Jack Johnson had a face-off with Jim Jeffries, one of the most magnificent boxing matches and now it is also marketed as the fight of the century. Johnson was the first black heavyweight champions in the US. Jim Jeffries who was boxing since long, was in this profession as a proven legend had negative feelings about black boxers and wanted to stop them. You see this was not only a boxing match but clash of ideologies. This match went on till 15 rounds and all through these rounds Johnson received racist taunts from Jefferies corner combined with hostile crowd of 20,000 people.

However, Johnson seemed to enjoy every minute of it! He received punch after punch that even opened his upper lip yet he persevered and didn’t get bothered with the comments. Johnson kept giving Jefferies a gory bloody but cheerful smile with every passing round. With his cheerful and playful response Jefferies became more enraged which drained a lot of energy from him. Till the time both of them reached round 15, Jefferies was completely burned out and he had lost the will to fight which helped Johnson to win the fight. When life punches you in the face just smile back, stay cheerful when facing something or someone with irrational judgements.

If you focus on every obstacle that life throws in the ways you will find that obstacles provide opportunities to improve the life in some way. But you need to face real obstacle you can imagine obstacles in the way. Facebook constantly does this, they identify the threats and incorporates those threats into their business. They notice and bought Instagram very early. After that Facebook borrowed stories from a competitor Snapchat and made it just different enough to not getting sued and by doing so they grew to new heights.

In the end start practicing the timeless art of turning trials into triumphs by seeing the upside of every setbacks. Adopt an “Amor Fati” attitude! That is love whatever life throws your way and don’t wish it to be different. When life punches you on the face smile back. Boxer Johnson taught us to be cheerful in the face of hate to disarm and outlast your opponents. But you need not wait for a setback to spot an opportunity. You can simply simulate setback ahead of time by simulating setbacks you can strengthen your approach and stay one step ahead of any threat.

I know not everyone has the time to read so what I wanted to do was give you the premise of the book and how we can turn everything that life throws at us into fuel to build us stronger in just a few minutes. Let me know how find this review and do check out this book, it’s a must read!


Holiday, R. (2014). The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph


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Stronger Together!

Hey there, I'm Parul, working in one of the Big 4s of consulting! 💼

By day, I'm decoding the business matrix, but by night, I transform into a book ninja, stealthily navigating the worlds crafted by the greatest authors📚✨


What's the secret sauce to my consulting wizardry, you ask? It's the lessons learned from the pages of both leadership meetings, strategies and bestselling novels 😉


I'm not just crunching numbers; I'm crunching captivating narratives 💖

Buckle up for insights that transcend industries and a blog where business acumen meets the magic of storytelling


#ConsultantLife #BusinessAndBooks 🌟

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