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The Obstacle is the Way Summary

Here’s The Obstacle is the Way summary. Learn how to turn trials into personal triumphs using some of the principles of Stoicism. Also learn how successful people have applied Stoicism to overcome difficult situations and problems.


The Obstacle is the Way author Ryan Holiday explains how to overcome problems using the principles of Stoicism. You will also learn how each problem is the way in achieving more.

The author also discusses how successful people such as John Rockefeller and Steve Jobs used Stoicism to overcome challenges. He also explains how to turn your biggest problems into your greatest opportunities.

About the Author

Ryan Holiday is a prominent writer and media strategist. He served as an apprentice under Robert Greene (The 48 Laws of Power author). Then he went on to help other bestselling authors and multi-platinum musicians.

Aside from The Obstacle is the Way, he also wrote Trust Me I’m Lying and Ego is the Enemy. You can learn more about him through his website

Main takeaways: The Obstacle is the Way Summary

Let’s discuss the key takeaways from his book:

  1. Study philosophy so you can handle life.
  2. What stands in the way becomes the way.
  3. Control your perception and discipline your will.

Study philosophy so you can handle life

What is philosophy? It’s the study of the fundamental nature of existence, reality, and knowledge. There are volumes of books about philosophy. But what’s the goal anyway?

The goal is to live a better life. Philosophy should serve as a guide to living a good life. We can spend countless hours in debating the nature of our existence. But if it doesn’t help us live a good life, we won’t get much use to it.

One of the most popular philosophies today is that of Stoicism. It serves as a guide for many successful people on how to navigate through life. It has a set of “guidelines” one can use so people can have ideas on what to do with their lives and how to respond to life’s situations.

That’s why the book, The Obstacle is the Way, draws its inspiration from Stoicism. It’s useful because people can learn how to handle life.

What stands in the way becomes the way

Read that again and you’ll feel you’re in a Zen-like state. But you don’t need the Zen just to realize its practical value.

The Obstacle is the Way is the perfect title for the book. Also remind yourself of that whenever you’re encountering a difficult problem. But how is that helpful?

For example you have business problems. It seems that there’s not much growth or potential in your business. That’s the obstacle. But it can also be your way. Why do you think there’s no growth in your business? Is it just your perception? What if you face the problem and see the potential of your business?

If truly there’s not much potential in your business, what’s going to happen? Well one option could be you should just try to sell the business. Or you could just spend as little time on it by delegating. Or you could just push further and explore other opportunities related to your business.

It’s a good mental exercise especially when you’re in a rut. The obstacle is truly the way. Let’s look at another example. We all have constraints in our careers, business, and our whole lives. But some people have capitalized on those constraints.

William Shakespeare is one of the best examples. What did he write? Sonnets that follow a strict rhyme scheme and specific structure. Most of us will think that we can’t do much with those restrictions. But Shakespeare worked with that. The rest is history as they say.

We can actually use the constraints to get more done. One common example is the deadline. For example you should finish writing a book within 6 months. At first it seems impossible.

But it will urge you to focus only on the essentials. You will set aggressive timelines. You will also set strict schedules. The constraint will help you to focus.

Author John Grisham writes one page a day. Jerry Seinfeld also writes every day. They have set constraints and hard deadlines for their work. But those constraints and obstacles also pave the way towards their inevitable success.

Control your perception and discipline your will

There’s nothing good or bad without our awareness. It’s only our perception. Once we recognize that, we can control it.

For example, the economy is going down. For many of us it means loss of jobs and business failures. But for the few people it’s different. They perceive it as an opportunity. How do they do that?

With a bad economy, prices are also going down. Companies are in a much tighter position to get more business. They’re now willing to offer lower rates. That spells opportunity for the entrepreneurs.

For example there’s the Dot Com Bubble. Amazon and eBay survived that. Look where they are now. They are now worth billions. Because of some crisis, they were able to get better deals. The bubble also got rid of many other companies. That led to less competition and dominance.

When someone loses a job, he has the tendency to lose heart and blame it all on the government. But it can be reframed as an opportunity. Maybe it’s just the right time to relocate and start a new life. Or maybe it’s time to start a new business.

One thing usually leads to another. Every problem can be transformed into an opportunity. It’s just about perception. We don’t have much control about our economy. But we have control over our perceptions and the next things we’re going to do.

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