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The Obstacle is the Way

The Timeless Art of Turning Trials Into Triumph

By Ryan Holiday
  • Read in 16 minutes
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  • Contains 10 key ideas
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The Obstacle is the Way by Ryan Holiday

In The Obstacle is the Way, Ryan Holiday brings the age-old wisdom of Stoic philosophy up to date. By examining the struggles of historical figures of inspiring resilience, Holiday shows not only how obstacles couldn’t stop them, but more importantly, how these people thrived precisely because of the obstacles. Holiday shows how we can turn obstacles to our advantage, and how we can transform apparent roadblocks into success, both in our businesses and our personal lives.

Key idea 1 of 10

Perception, action, and will are the keys to turning obstacles to our advantage.

When faced with an obstacle, most of us get angry, fearful and frustrated. We think it will derail our plans and hinder our progress. But obstacles can actually become advantages, and far from limiting us, they can lead us to success.


To turn an obstacle into an advantage, we have to focus on three things.

First, we should focus on our perception of the obstacle. If we can see an obstacle in the right light, we can reveal the hidden possibilities we can use to our advantage.

This was the key to the oil baron John D. Rockefeller’s success. During a financial crisis in 1857, Rockefeller, only 18 years old, watched how those who panicked behaved, and observed what they did wrong. By analyzing their failures, Rockefeller was able to see the obstacle – the Panic – in another way. He was then able to perceive the advantages the crisis offered, take action and start on his way to becoming one of the world’s richest men.

But perception alone is not enough. When you are faced with an obstacle, you also need to respond with the correct action.

The correct action is born from the combination of creativity and flexibility. For example, at the beginning of the twentieth century, Amelia Earhart wanted to become a great pilot, but an obstacle stood in her way – back in those days, women just didn’t become pilots. So she took a mundane job to survive, but kept looking for creative ways to accomplish her dream.

One day she received a call saying that someone would fund the first female transatlantic flight, but she could only be an unpaid passenger. Though this was far from what she wanted to accomplish, she accepted – and this jumping off point led to a career as a great aviator.

After identifying the best way to perceive an obstacle and the best action to overcome it, we use our will to persevere until the obstacle has been overcome.

Over the next few blinks we'll look at each of these in more detail – starting with perception.

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