The Obstacle is the Way – The Stoic Strategy to Overcome Anything.

“The first rule is to keep an untroubled spirit. The second is to look things in the face and know them for what they are.”

Marcus Aurelius


First, see clearly.

Next, act correctly.

Finally, endure and accept the world as it is.

These are the words of Ryan Holiday and the thesis of his 2014 best-selling book ‘the obstacle is the way’. Marketed as ‘The Ancient Art of Turning Adversity to Advantage’, Holiday, masterfully employs the skill of intertwining the wisdom of ancient philosophy into the applicable and practicable use in 21st century living. Described by Robert Greene as ‘a book for the bedside of every future – and current – leader in the world’, this comprehensive guide offers a pathway into overcoming obstacles and furthermore turning them into bridges towards success.

It is a life truth, that at some point we will all face obstacles, some big, some small. Admittedly, we are all given different starting blocks in life, as well as facing completely unique factors, such as our genetic code, that are completely out of our control. However, it nevertheless remains, regardless of their nature or magnitude, that we all face are own individual challenges and setbacks, yet as Ryan outlines, it is the way in which we respond, which is what truly matters. Will you shrink in the face of adversity? Or will you rise to the obstacle and turn it into your advantage? As the saying from a king in an old Zen story goes... ‘The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.’

The thesis Ryan outlines in his book is split into three parts; perception, action and will. Each component is both individually whilst also collectively important in overcoming any obstacle whilst also turning it into an advantage. Perception details, as Ryan puts it 'how we see and understand what occurs around us - and what we decide those events mean'. From my experience, it is this first part which is most crucial to overcoming life’s challenges. Before we can hope to tackle our problems, we must first seek to approach them with correct intention and clear thought. Through the practice of meditation, it becomes especially clear that we are so often clouded and skewed by how we perceive and interpret the obstacles we face, albeit at a predominantly subconscious level. As Dr Gabor-Mate questions in his interview with Tim Ferris… why is it that in most situations we fear or assume the worst in circumstances and people, without even a second consideration to the unlimited possibilities which may have caused something to happen or someone to act how they did. Naturally we are all guilty of presuming the worst in people when we have been wronged (or at least thought to have been), but surely this isn’t healthy and in 99% of cases it is certainly a counterproductive stance to hold. As Ryan writes 'there is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means.' The solution is easy... 'we defeat emotions with logic... logic is questions and statements. With enough of them, we get to root causes (which are always easier to deal with'). Don’t overcomplicate the nature of your problems, it is counterproductive and unnecessary, even despite our natural tendency to do so.

Once we have perceived the nature of our supposed obstacles correctly, we must take appropriate action, both intentionally and with purpose. It’s important to note this requires a consistent effort, the practice of action doesn’t involve a single moment in time, but instead a continuous commitment to overcome and accomplish. As Ryan states 'Too many people think that great victories like Grant’s and Edison's came from a flash of insight. That they cracked the problem with pure genius. In fact, it was the slow pressure, repeated from many different angles, the elimination of so many other promising options, that slowly and surely churned the solution to the top of the pile. Their genius was unity of purpose, deafness to doubt, and the desire to stay at it'. Real progress is persistence and involves true hard work. It is often easy in hindsight to label our victories in tough times as simple and momentary in their effort. However, when you truly look back and reflect on your proudest achievements, they always required sustained and continuous effort, as well as a great deal of tenacity to overcome the moment to moment, mental and physical impediments that tried to block you. As James Clear outlines in ‘Atomic Habits’, it is the compounding results of our actions, however small which determine the nature of our overall success or failure when facing particular obstacles.

Furthermore, a lot of what prevents us from taking action against our setbacks is the false belief that waiting, will eventually allow the perfect conditions for us to act and overcome. During the 2008 financial crash, many companies became defensive and highly adverse to risk and innovation. In the face of such financial uncertainty, waiting for the right conditions to arise, they hoped to shelter themselves from the storm. On the other hand, some firms saw the opportunity of such an event and the clear reshuffling of market powers, to grow and innovate even in the face of such risk and clear adversity. Notably, this was the case with Elon musk and his company SpaceX. After 3 failed attempts to launch the Falcon-1 rocket into orbit, the 4th attempt in September 2008 marked a do or die situation for the company. Musk could easily have folded before this attempt, in the face of such pressure and lack of financial support to back more launches it would be understandable, especially considering his other company Tesla motors was also on the ropes at this time. Despite this, and the clearly imperfect conditions, Musk pressed on, and the launch was a success, (after careful iteration on attempt 3’s mishaps). Marking the first commercially operated rocket to orbit Earth, Musk was able to secure $1 billion in funding from Nasa and continue his relentless mission to revolutionise the space industry. Holiday in the chapter titled ‘get moving’ writes ‘Just because the conditions aren’t exactly to your liking, or you don’t feel ready yet, doesn’t mean you get a pass. If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started.’ There is never a better time than now. Sulking over your obstacles does little good, so take action and you are bound to see the fruits of your labour eventually.

The final component in Holiday’s equation is will. 'Will is our internal power, which can never be affected by the outside world... If action is what we do when we still have some agency over our situation, then will is what we depend on when agency has all but disappeared'. Without will and an internal flame, our ability to overcome obstacles are almost futile. We must all have a little bit of that inner strength, that grit and determination to succeed. It’s part of being a human and it so often separates the weak from the strong. When researchers sought to identify the attributes of success across many fields, from sport to medicine to entrepreneurship they found not the level of intelligence, or the level of finical support to be the determinant to one’s eventual success (although these still play a role) but the level of grit and persistence in which they had to push through and master their craft, which most often determined their level of success. Extrinsic motivation only goes so far in pushing us forwards; therefore, we must learn to hone our intrinsic desire to succeed in order to overcome our obstacles and setbacks.

Holiday also refences the idea of 'Amor Fati' Loving everything that happens to us. Whatever happens, if we learn to love the progression of fate then we can truly never be upset, why lose energy over such matters that are fundamentally out of our control? ‘That is not to say that good will always outweigh the bad. Or that it comes free and without cost. But there is always some good – even if only barely perceptible at first – contained within the bad. And we can find it and be cheerful because of it.’

Holiday ends this chapter discussing the idea of meditating on your mortality - a very much stoic strategy – Memento Mori (originated in Ancient Rome and means ‘remember death’ In Latin). He says 'Thinking about and being aware of our mortality creates real perspective and urgency. It doesn’t need to be depressing. Because it's invigorating. And since this is true, we ought to make use of it. Instead of denying - or worse, fearing - our mortality, we can embrace it. Reminding ourselves each day that we will die helps us treat our time as a true gift.' This idea is frequently found in Marcus Aurelius’ Mediations. Marcus often references the inevitability of death whilst recognising from on a broader scale, the limit of time we all have on earth… 'None of us have much time. And yet you act as if things were eternal-the way you fear and long for them... Before long, darkness. And whoever buries you mourned in their turn.' At first, this notion can be perceived as dark and overly gloomy. However, the more this point is considered, the more the profundity in this viewpoint can be appreciated. The inevitability of death is incredibly liberating, stop worrying and start doing. If Each day we are closer to death, then why waste this so precious yet temporary opportunity to live before the sands of time forget we ever existed.

To conclude this book, Ryan reminds the reader that the pursuit of philosophy and a virtuous existence is very much centred around practice and not study. We must constantly strive to apply what we learn whilst accepting the reality we will never be perfect in the face of life’s ever-changing challenges. Even Marcus Aurelius, Seneca and Epictetus, the greatest of histories stoic philosophers had their personal struggles in adherence with the ideals of their philosophy. Remember 'Philosophy was never what happened in the classroom. It was a set of lessons from the battlefield of life... an extension of you... and as Marcus once wrote, it was meant, to make us boxers instead of fencers - to wield our weaponry, we simply need to close our fists.' Therefore, next time you face an obstacle, no matter its size, look for the opportunity and seek to overcome it with uncompromising action and will. In the eyes of the stoics, success is determined not in the nature of our outcomes but instead in the sincerity and persistence of our efforts. With proper perception, action and you will always triumph. Remember, as holiday writes, we must…

First, see clearly.

Next, act correctly.

Finally, endure and accept the world as it is.

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