The Obstacle is the Way

As a child in New Zealand, men were often described as ‘stoic’. It seemed to mean a stern toughness. Even now it brings to mind steely-eyed All Blacks. Pinetree Meads striding across the field with the ball in one massive hand, fending the opposition off with the other. They seemed to be impervious pain. Wayne ‘Buck’ Shelford played on after tearing a testicle and losing four teeth in a ruck.But, while admirable qualities in an All Black, ‘stoic’ seemed remote for mere mortals. But stoicism is both much more accessible and far different than I thought.

Stoicism is the hot new thing in philosophy right now. Odd for a school of thought that has been around for well over two thousand years. It’s stoicism that Silicon Valley startups and NFL teams are turning to to give them the edge. Much of that is down to Ryan Holiday and his book, The Obstacle Is the Way.

Stoicism was an ancient Greek school of Philosophy. It taught practical steps to achieve well-being or happiness in your life. It’s most famous practitioners are a slave, a Senator and an Emperor.

Statue of Marcus Aurelius on a horse

The Emperor was Marcus Aurelius, known as the last of the five Good Emperors. Rare amongst the rulers of Rome in that he wasn’t a madman and worked for the safety and well being of his Empire. Throughout his long reign he wrote a journal, a private diary of his thoughts and ideas. Today we call it Meditations. It was to remind him to keep moving forward and not get bogged down in bullshit and ignore the haters.

Ryan Holiday’s life changed when he read Meditations and the lessons it contains. Here he’s written his own take on the thoughts of Marcus Aurelius. He uses stories throughout history to illustrate the depth and appeal of stoicism.

Part self-help and part history. Obstacle defies the modern trend of philosophy and encourages action, not contemplation. The book’s structure is simple and lean and well laid out. Each chapter is short and concise. The book has three main parts: Perception, Action and the Will. Stories of figures throughout time illustrate his points. From Lincoln and Napoleon to Amelia Earhart and Ghandhi.


How you look at an obstacle. Nothing is as bad as you think, or ‘nothing either good or bad but thinking makes it so’ as Shakespeare put it. We choose how we respond to problems, the problem is there, our response is the only thing we control.

Hurricane Carter

The only real thing you can control is your response. Not the obstacle itself, that already happened. Holiday tells the story of Rubin Hurricane Carter. When falsely imprisoned, he refused to consider himself a prisoner. Sure he was locked up but that didn’t change who he was. He refused prison food, parole hearings and working in the commissary. Punished with solitary he spent all his energy working on his case. When he did get released, he resumed his life. No civil suit or apology from the court, he didn’t need it as they hadn’t taken anything from him.


 The response you take. Moving is the answer, dithering is not. Once started, keep moving. Persist and resist. It’s the long haul that matters.

But acting doesn’t mean acting out. It’s right action that we need. And don’t confuse emoting about a problem with solving it. Use that energy well.

After all the observing and perceiving, then it’s time to move. Watching an obstacle won’t help you move it, you must move yourself.

Start. Somewhere, anywhere but get moving. You create your own momentum.

The Will

The only thing we control completely. It’s our internal power and it is not affected by the outside world. Unless we let it.

To help with this the Stoics talk about the Inner Citadel. A castle of the mind impenetrable by external forces. But it needs to building and then maintaining and reinforcing. When times are good you make your body and mind strong to endure when times turn bad.

It’s not just what you can learn from this book that I love but the other avenues it opens up. Each story leads to something else. The stories of historical figures give you a taste for what they went through and lead to a desire to learn more.

Gandhi Salt March

Holiday talks about Ghandi using non-violence against the British. The world’s largest ever Empire, defeated by a little man in a loin cloth walking to the ocean to get salt. Or the Russians retreating before Napoleon and letting the winter do its deadly work for them.Stoicism has many similarities with Buddhism, meditation being one of these. Premeditatio Malorum is an astounding sounding phrase, like a spell from Harry Potter. It is the stoic maxim of ‘premeditation of evils’.

Like the samurai, who meditated on all the different ways he could die, to free himself of the fear of death. The Stoic spends time thinking of the worst outcome that could happen. When it doesn’t happen it’s a relief. If it does happen, he has prepared and doesn’t get paralysed by shock.

I read Obstacle before I needed it. When life took an unexpected and scary turn the lessons from this book helped in dealing with them. I’ve gone on to read much more Stoic philosophy and embrace it as a system for living.

I’m a great fan of Ryan’s writing and named this website after something he wrote. His latest book, Ego Is the Enemy is on the way from the nearest Amazon bunker and I expect great things. A highlight of each month is his reading recommendation email. Take care as it can wreak havoc on your Amazon account.

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  1. July 30, 2016

    Excellently written, sir! The motivating talk was refreshing! Will surely check out the books you’ve mentioned.

  2. September 21, 2016

    […] not just tales of the All Blacks,  there are other examples. Much like Ryan Holiday he uses Vince Lombardi, Bill Walsh and other greats of American […]

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