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Don’t See Obstruction as a Sign to Give Up. Instead, Make the Obstacle the Way.

Ryan Holiday’s book, The Obstacle is the Way, takes its name from a famous line from Marcus Aurelius, the Roman emperor and Stoic philosopher:

“The impediment to action advances action. What stands in the way becomes the way.”

The book’s subtitle tells you a little more about what is going on here – The Timeless Art of Turning Trials into Triumphs – and, for business leaders, it’s a text rich with tips, examples, and wisdom about how to be better at turning challenge to your own advantage. A mantra by which I have lived throughout my professional life.

The book derives many of its core messages from the philosophy of Stoicism, the school of thought that emerged in Athens in the third century BC. Holiday’s approach to this philosophy updates it for the twenty-first century business world. We should embrace, not fear or ignore, difficulty and challenges and we should change our mindset to see problems not as failures but as moments in which to prove our excellence. I have touched on this topic a couple of times already both in my article on stress and also on the Obstacles to Implementation.

Holiday focuses on three ideas central to his and to the Stoics’ philosophy: perception, action, will. And these ideas – “how we think about things, what we do about them, and how we accept or endure that which we cannot change” – are the psychological basis upon which both you and your business will thrive or die.


When your business faces a problem, what do you do about it? Do you ignore it and hope it goes away? Do you break out in sweats of stress and anger? Or, do you get a grip, sit down, and show yourself and the world that you can excel even in tough times?

The main problem with problems, with difficulties, with challenges is the way you perceive them. Quite simply, obstacles are not obstacles until you perceive them as such.

Think about customer complaints. Are these damning personal attacks, indictments of your complete failure? Or are they opportunities to identify, and find solutions for, problems that you hadn’t noticed, or that had been lurking around too long? Put your emotion aside and try to think and to see things differently.

Before you see them as obstacles, take a step back, and see them for what they are, really. Most challenges aren’t going to kill you, so use them as an opportunity to test your mettle – and act.


The Stoics were all about duty, about action. Good people were not to be judged on what they said or thought, but on what they did. Things were to be done virtuously, properly and rightly, even the most humble, the most banal, of tasks.

So, act. You’ve identified the problem in a way that doesn’t overwhelm you, that doesn’t upset you, that doesn’t scare you. But now is not the time for paralysis, hesitation, or procrastination. Facing difficult tasks makes you (and your team) more resilient: it proves to you and your team that you can deal with issues, it tests and builds the skills that can be utilised later.

But, for those who have read my article What is Structure, Visionaries listen up: finishing is the focus. See the task through to the end. Make sure it is done well, make sure it is done virtuously, make sure you do right by yourself and by your customers and staff. Those customer complaints? Don’t sweep them under the rug. Identify the root cause of the problem they flagged up, and deal with it. Obstacles provide the opportunity for action that improves you, your team and your business.


This is about your attitude to the world, recognising that tough moments pass, and handling difficulty in a way that is positive and productive. As Andy Grove, the founder of Intel, once said: “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”

What is important is focusing on the things you CAN control, and knowing the things that you cannot. Natural disasters, legislative change, and competitor innovations are all out-with your control. However, structural measures and innovations you introduce to ensure your business is more resilient ARE within your control – and they will make the difference in challenging times. A friend of mine once said “keep your eye on the field, not the scoreboard” a reminder that you cannot influence your competitors’ performance but you can influence yours. The scoreboard will show the result.

An interesting idea that Holiday suggests, is to consider a ‘pre-mortem’ for every plan that you are about to roll out. I automatically have been doing this for years, asking where could this go wrong and putting in place measures to minimise or even eliminate the risk.


Embrace the fact that mistakes are inevitable: we can never eliminate all the risks but it is wise to minimise them where possible. When they happen, view them as valuable feedback, implement structural elements into your business to minimise or even eradicate them and that way you can improve your business.

Remember, challenges are opportunities to activate your team’s problems solvers; help them solve them and achieve more than they thought possible. Allow them to grow, shift their mindset and rise to the challenge!

Then they too can learn to make the obstacle the way.

Make the Obstacle the Way: Action Points.

  • Try the Five Whys. Asking ‘why?’ five times takes you through a problem and out the other side.
  • Get out and think about something different. When you are encountering a problem, don’t let it get you down. Get out instead, get away. Your creative problem-solving faculties will be all the better for it.