Ryan Holiday, ‘The Obstacle Is The Way: The Timeless Art Of Turning Trials Into Triumph.’ 2014 Portfolio Hardcover, 224 p.
Holiday’s premise, and that of the philosophers whom he quotes rigorously, is that any challenge in life is best met head on. I was immediately intrigued by the book’s brash attitude. Over and over again, the point was made that obstacles, challenges and trials are essential to the human experience, and attempting to live without them or constantly avoid them is meaningless and harmful.
Breaking the philosophy into three distinct methods, he highlights Perspective, Action, and Will as the means to defeat any hardship.
Perspective, the first, defines how to approach a setback. It is the “fundamental notion that girds not just Stoic philosophy but cognitive psychology: Perspective is everything.” Take an obstacle for what it is: not how it makes you feel, what it might imply for the future, what its cause may have been, etc; these curiosities are just a distraction that do not contribute to its defeat. There is power in the fluidity of perspective, and that facility is an advantage over the stasis of an obstacle.
“Don’t feel harmed – and you haven’t been.” – Marcus Aurelius
The second discipline is Action. “What people who defy the odds do… They start. Anywhere. Anyhow. They don’t care if the conditions are perfect or if they’re being slighted. Because they know that once they get started, if they can just get some momentum, they can make it work.” Action is what follows perspective: once we condition ourselves that an obstacle is only fearful if we think of it as fearful, then we may act to overcome it. Historical examples are packed in to illustrate this concept: Ameila Earhart flew in the face of doubt and discrimination, Ulysses Grant suffered hard losses and had to discard military convention, Thomas Edison experimented with six thousand possible filaments to use in his first light bulb. These stories of right and persistent action “…are not the exception to the rule. They are the rule. This is how innovation works,” says the author. An obstacle requires action, and right action grows naturally stronger according to the weight of the obstacle.
“When the fire is strong, it soon appropriates to itself the matter which is heaped on it, and consumes it, and rises higher by means of this very material.” – Marcus Aurelius
Will. “Our final trump card.” The third discipline of beating challenges. Will is the essence of the fight, and as described in the book’s final section, it is the last thing we may hold on to when action seems to fall short. We may change our perspective, and we may begin to act – but when the first act fails, and the second act follows – it is will that will stand us back up for a third, fourth, or fiftieth try. Abraham Lincoln is offered as the personification of willpower: he was raised in poverty, but educated himself. He lost his mother as a child, his first romantic love passed away, yet he found political office. He suffered from what is now understood as clinical depression, but in his time was just considered an unattractive personal habit of ‘melancholy.’ In spite of all his disadvantages, he often repeated the phrase – “This too shall pass.”
Meditation on the persistence of obstacles is a way to enhance the will: “Behind mountains are more mountains.” Being certain that another challenge exists after the current one means that slowing down or losing strength can only make the next problem more difficult. Being persistently mindful of the cyclical nature of opposition strengthens the will.
In the book’s last pages, a Stoic Reading List is prepared. Inspired by this contemporary reading of classical concepts, I dug out my old copy of Epictetus’, ‘the Art of Living,’ to see how much of Holiday’s narrative was comparable to the wisdom of the ancients. Epictetus states: “Men are not disturbed by things, but by the views which they take on things.” My copy of ‘the Art…’ which had sat untouched on a shelf for years, has since been relocated to my bedside. Now I can take 5 minutes every day to remind myself: The Obstacle Is The Way.