Bookworm: The Obstacle Is The Way

Ryan Holiday outlines the timeless art of turning trials into triumph.

What’s the big idea?

We should perceive our problems not as insurmountable obstacles but as paths to achievement, according to author Ryan Holiday (former marketing director for American Apparel).

Who has actually managed to do that?

He gives the example of John D Rockefeller, one of the richest men who ever lived. The Panic of 1857 – one of the worst financial crises in US history – turned out to be the catalyst for the businessman’s fortune. Where others panicked amid the financial instability, Rockefeller retained an icy calm. He used the uncertainty of others to his advantage, surviving on logic and resilience.

The lessons from Rockefeller’s ascent to the top, says Holiday, are that we should only worry about things within our control, we should try not to regret the past or worry about the future, focusing only on the here and now, and we should try not to let emotion get in the way of our objectivity.

His success could be a fluke, of course. Who else embodies this?

Another person from whom we can learn, says Holiday, is Rubin Carter, who didn’t let being falsely imprisoned for 19 years stop him retaining the moral high ground, educating himself in jail, and emerging a free man.

And then there’s George Clooney’s path to success which, says Holiday, is another illustration of the all-important power of perception. After failing to land various roles in Hollywood, the actor began to see the problem as the industry’s, not his; in other words, he started perceiving himself not as inferior but as the talented actor for whom the casting directors had been waiting.

What’s Holiday’s theory around perception?

That it’s about not making a problem unnecessarily difficult. You don’t ignore the difficult parts of a challenge; you just make the problem surmountable by keeping the end in sight, taking one bit at a time, and acting rationally at all times. It’s about discipline more than anything else.

Is there a process for all of this?

Funny you should say that. Holiday, borrowing from the philosophy of a celebrated college soccer coach, is quite a fan of the word ‘process’: everything will feel impossibly daunting if you think only about the destination. Instead, focus on the tiny steps that comprise the journey. These are manageable; not scary at all.

This is what separates high achievers from the rest of the population: that they are willing to grind out the long but relatively straightforward task at hand. You need to trust this process, says Holiday.

And if the process doesn’t work?

Then at least you’ve tried. There will be things that aren’t just arduous, they’re actually impossible for you to solve or fix. Trying will have taught you something, and will have helped hone the skills you used in the attempt.

The stoics, says Holiday, talked of an ‘inner citadel’ – an impervious place in your mind that will help you remain calm when the fate of the world seems to be against you. There will always be things out of our control; the book mentions Theodore Roosevelt’s childhood asthma, for example. Rather than limit his ambitions, Roosevelt was prepared for what life threw at him – he improved his lung strength through exercise and went on to overcome the various other hurdles in his way.  He had perseverance – another p-word of which Holiday is fond.

Could be down heartening, though. How could I combat that?

Reflect on death, says Holiday, as it’s perhaps the greatest obstacle of all. Once we consider the finality of death, the obstacles we face in our day-to-day life should seem less daunting. Compared with death, nothing ought to frighten us.

What practical lessons can I take and use from this?

• Focus on continually improving what you do.

• Imagine that you are a friend of yours giving yourself advice. It may help you look with more objective eyes at whatever predicament you’re in.

• Remember that some things won’t go your way. Look at them as opportunities to learn, not to get angry at the world.

• Rehearse the things that could go wrong, so that you’ll be better prepared if they happen.

• Remember that your perception of the world distorts the way that you behave. Try to step back and look as objectively as possible at the problem you are facing.

What am I most likely to say after reading this book?

 “At least it’s not as daunting as death.”

What am I least likely to say after reading this book? 

“Too many obstacles; I give up.”