Reading List: The Obstacle is the Way

The Obstacle Is the Way by Ryan Holiday has become very popular and highly recommend in some circles. It has been on my reading list for some time, and I finally got a chance to read it. I couldn't recommend it enough.

At it's core, this book is about ancient Stoic Philosphy. So what does Stoic philosophy have to do with running a successful business?

Every obstacle is unique to each of us. But the responses they elicit are the same: Fear. Frustration. Confusion. Helplessness. Depression. Anger.

A big part of being a small business owner is dealing with obstacles and set back. As the owner, you are responsible for everything. It's hard not to take setbacks in your business personal. This book provides a framework of thinking to deal with issues and keep moving forward. Find the opportunity in the problem, or just see the problem for what it is. It helps keep our emotions and thinking in check.

Owning and running a business is about moving forward. If you let set backs slow you, or stop you, you'll business will fail. This books helps you be in the right frame of mind to keep moving.

Stoic philosophy has been described as an “Operating System for Life” (Tim Ferriss).

This is probably the most highlighted book I have read. The style of writing lends itself to very easy to understand and remember quotes and passages.

The book is on the shorter side, and is written in a way that makes it easy to refer back to later. You can pick up this book and skip around or refer to specific sections. It definely one to keep close on your bookshelf.

I can't share all my highlights from the book, because it would be most of the book, but here are a few favorite quotes.

Keep emotions in check.

When people panic, they make mistakes. They override systems. They disregard procedures, ignore rules. They deviate from the plan. They become unresponsive and stop thinking clearly. They just react—not to what they need to react to, but to the survival hormones that are coursing through their veins.

What are you missing.

As Gavin de Becker writes in The Gift of Fear, “When you worry, ask yourself, ‘What am I choosing to not see right now?’ What important things are you missing because you chose worry over introspection, alertness or wisdom?”


Keeping perspective.

Objectivity means removing “you”—the subjective part—from the equation. Just think, what happens when we give others advice? Their problems are crystal clear to us, the solutions obvious. Something that’s present when we deal with our own obstacles is always missing when we hear other people’s problems: the baggage. With other people we can be objective.

Starting your business.

Our understanding of the world of business is all mixed up with storytelling and mythology. Which is funny because we’re missing the real story by focusing on individuals. In fact, half the companies in the Fortune 500 were started during a bear market or recession. Half.

What is genius?

Genius is the ability to put into effect what is in your mind. There’s no other definition of it. —F. SCOTT FITZGERALD

Believing in the problem over the solution.

Our perceptions determine, to an incredibly large degree, what we are and are not capable of. In many ways, they determine reality itself. When we believe in the obstacle more than in the goal, which will inevitably triumph?

Making a problem bigger than it is.

Problems are rarely as bad as we think—or rather, they are precisely as bad as we think. It’s a huge step forward to realize that the worst thing to happen is never the event, but the event and losing your head. Because then you’ll have two problems (one of them unnecessary and post hoc).

Keep moving forward.

Think progress, not perfection.

External factors.

Your world is ruled by external factors. Promises aren’t kept. You don’t always get what is rightfully yours, even if you earned it. Not everything is as clean and straightforward as the games they play in business school. Be prepared for this.

Work in reality.

You know what’s better than building things up in your imagination? Building things up in real life.


What is philosophy

Philosophy was never what happened in the classroom. It was a set of lessons from the battlefield of life.

If you've read the book, feel free to share your own favorite quotes in the comments. If you haven't read it yet, be sure to check it out.

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