The Obstacle Is The Way – by Ryan Holiday

All of us have obstacles. They come in many shapes and sizes. But whatever we face, we have a choice: will we be blocked by obstacles, or will we advance through them. Holiday, through the lens of stoicism gives us a framework of perception, action and will, to turning our greatest challenges into our greatest opportunities. And of course, every time you overcome one obstacle, there’s another one coming right around the corner…

‘The ancient art of turning adversity into advantage’

The Obstacle Is The Way Summary

All of us have obstacles. They come in many shapes and sizes. But whatever we face, we have a choice: will we be blocked by obstacles, or will we advance beyond them. Holiday, through the lens of stoicism gives us a framework to turn our greatest challenges into our greatest opportunities: perception, action, will. Perceptions involve shifting your perspective from viewing obstacles as a negative to an opportunity, Action is all about taking action, and Will is about staying on the path and keeping yourself on track. And, of course, every time you overcome one obstacle, there’s another one coming right around the corner…

We all have something standing in our way. Maybe we’re dissatisfied with our jobs, our relationships, or our place in the world. We’re all trying to get somewhere different, but there is always something standing in our way, something blocking our path: an obstacle. For some people, this obstacle seems insurmountable, so we stand still and do nothing. This frustrating, unfortunate, problematic, unexpected thing prevents us from doing what we know we should do.

This book is about shifting your reaction from ‘this is bad’ to ‘how can I make this good?’. We all think that there’s something holding us back from achieving our best. It might be physical – race, size, age, distance, disability, money, or it might be mental – fear, uncertainty, intelligence, inexperience, prejudice. The people who see these as obstacles will be stuck, the people who can accept them and move any anyway are the people who will ultimately achieve. As Marcus Aurelius said: “what stands in the way becomes the way“. Never forget, within every obstacle is an opportunity to improve our condition.

Whatever we face, we have a choice: will we choose to be blocked by the obstacle, or will we choose to advice through them and over them and beyond them?

PERCEPTION

Practice Objectivity. Whether out loud or just to yourself, you’ll often say something resembling “this happened and it is bad”. We say it as one idea, but we’ve actually conflate two independent statements. “This happened” is fact, it’s objective, it’s true – it happened. “It is bad” is our perception, we’ve judged the event, we’ve applied our personal biases and filters – we’ve turned an objective event into a subjective assessment. We can’t control the first part, but we can control the second part by shifting our perceptions. We can’t control what happens, but we can control how we react. We can’t control external events, but we can control what we do next. 

Is it up to you? You can divide things into two buckets: things within your control and things outside of your control. Focusing solely on the things within our control magnifies and enhances our power, worrying about things outside of our control saps our power. The prescription is simple: if you can’t control it then accept it and don’t worry about it, so focus your efforts purely on the things that you can influence. 

Finding the opportunity. Let’s use an example I’m sure we’ve all encountered: having a bad boss. You may be at the end of your rope and ready to quit. This may seem like a losing scenario, but there are many opportunities for you here. You could analyse what makes him or her a bad boss so that you can learn to be a better one. You have an opportunity to practice patience or practice standing up for yourself and being less of a ‘yes man’. If you plan on leaving anyway, you’ve got the perfect place to practice a new style of working, a new time management system, or a new way of communicating – if it doesn’t work you’ll soon be gone anyway. Where one sees a crisis another sees an opportunity, where one loses control of emotions another can remain calm, when one sees limitless success another sees reality with ruthless objectivity. 

ACTION

Get moving. The first step to hitting a home run is taking the bat off your shoulder and giving it a swing. You’ve got to start in order to get anywhere. If you’re trying something, you’re already ahead of most people who prefer to play it safe and follow the rules. But ask yourself – could you be doing more? You probably could. There’s always more. At a minimum, you could be trying harder. You’ve gotten started – that’s the hardest part – now keep going, stay persistent, and invest more of yourself into the project.

The Mindset: don’t quit. Once you start attacking an obstacle, quitting is not an option. Even the thought of quitting cannot enter your head. Abandoning your current strategy for a more promising path might be a good idea, but giving up altogether is not. If you can picture yourself quitting you may as well throw in the towel now, it’s basically done. Don’t allow the thought to creep into your mid: you’re not going to quit, you’re not going to let the obstacle win, you’ll keep going no matter what.

Prepare for none of it to work. In every situation, that which blocks our path actually presents a new path for a new part of us. If someone you love hurts you, you have a chance to practice forgiveness. If your business tanks, there is a chance to practice acceptance. If you get laid off from your job, you have a chance to develop your skills or try something completely new. Duke Ellington said that “problems are a chance for us to do our best”. 

WILL

The discipline of will. Always prepare ourselves for difficult times. Always accept what we’re unable to change. Always manage our expectations. Always persevere. Always learn to love our fate and what happens to us. Always protect our inner self. And of course, prepare to start the cycle once more.

Anticipate the worst. Some business books suggest conducting a ‘pre-mortem’. Rather than a post-mortem, where you analyse why something died or why a project failed, conduct this at the start: imagine that the project you’re about to begin working on has just failed and ask yourself what were the major causes of its failure. By thinking about the worst case scenario ahead of time, you’ll work harder to find the flaws or traps to avoid and give your project a greater hope of success.

Momento Mori. Remember that you are mortal. Holiday advocates for the power of meditating on our own mortality. You can die at any moment. You’ve only go one shot, and when it’s over it’s over. So make it count. “We forgot how light our grip on life really is”

Prepare to start again. The great law of nature is that it never stops. Just when you think you’re done and you’ve got over every obstacle standing in your way and you’ve finally achieved what you set out to achieve, there is another obstacle even bigger than the last lurking somewhere just beyond the horizon…