Business Book Review: The Obstacle is the Way by Ryan Holiday

From the traumatic to the tiny, The Obstacle is the Way is the catch-cry for overcoming adversity. For turning what stands in your way, into your greatest triumphs.

My Rating: ★★★★★

Length: 224 pages

Publisher: Portfolio

Released: 2014

Key Takeaways for Personal Branding

Ryan Holiday’s The Obstacle is the Way is the mantra for every adversity you face—the Stoicism enthusiast advocates for turning adversity to your advantage. As the reader, the catch-cry almost excites you about the challenges ahead.

From Amelia Earhart to Steve Jobs, Holiday uses iconic stories to prove his point- that challenge for some of history’s greatest figures led to their triumph.

Control and Perception

In keeping with Stoic philosophy, The Obstacle is the Way encourages you to focus on what you can control and let go of the rest:

“Focusing exclusively on what is in our power magnifies and enhances our power.”

“There is always a countermove, always an escape or a way through, so there is no reason to get worked up. No one said it would be easy and, of course, the stakes are high, but the path is there for those ready to take it.”

The Obstacle is the Way proposes there is no good or bad - only our perception of it makes it one or the other:

“There is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means.”

Turning Obstacles into Opportunity

Once you’ve controlled your emotions and steadied your nerves, learn to look for the opportunity in every experience:

“See things for what they are.
Do what we can.
Endure and bear what we must.

What blocked the path now is the path.
What once impeded action advances action.
The obstacle is the Way.”

Instead of attacking obstacles, obstacles can also be used against each other.

God Willing

Your will is always yours. It cannot be taken by external forces:

“Will is our internal power, which can never be affected by the outside world. It is our final trump card.”

But, even with their focus on control, the Stoics also mastered detachment. Instead of the “will to win” mindset, they propose a mindset shift to “God willing”. Taking persistent action, while also having some sense of surrender to the universe. There is no need for attachment to one plan, as you know that with every obstacle, there is a new unforeseen opportunity you are destined for:

“Persistence is an action. Perseverance is a matter of will. One is energy. The other is endurance.”

Favourite Quotes

“Failure shows us the way—by showing us what isn’t the way.”

“The world is constantly testing us. It asks: Are you worthy? Can you get past the things that inevitably fall in your way? Will you stand up and show us what you’re made of?”

The Obstacle is the Way by Ryan Holiday. Available on Amazon.