The Obstacle Is the Way

“While it’s true that someone can impede our actions, they can’t impede our intentions and our attitudes, which have the power of being conditional and adaptable. For the mind adapts and converts any obstacle to its action into a means of achieving it. That which is an impediment to action is turned to advance action. The obstacle on the path becomes the way.”


The title of today’s chapter stood out to me, because it exactly matches the title of another, earlier book by author Ryan Holiday called The Obstacle Is the Way. That book is stoic-influenced as well and discusses how to overcome obstacles and make them part of the solution.

Holiday must have liked that title so much that he included it as a chapter title in The Daily Stoic, and that’s what we’re discussing here. What’s it all about?

It’s normal to dread obstacles — they’re essentially blocking you from completing your plan. You wouldn’t be human if you didn’t occasionally groan when you meet an obstacle.

But you don’t have to dread them. As a stoic you can try to actually welcome challenges as simply “speed bumps” along the way, and view them as an opportunity to show what you’re capable of overcoming, to show your mettle and your character.

A stoic will attempt to turn a problem on its head — or stand on their head themselves, for perspective! They’ll look at it from a new angle, as a chance to demonstrate their skills.

If it doesn’t work out, and you experience failure, view it as an opportunity to learn from mistakes made and apply that knowledge forward. A chance to “reset”.

Ordeal vs. Adventure

It’s really about perspective, isn’t it?

One of my favorite quotes comes from Bob Bitchin, skipper of the Lost Soul and an amateur philosopher in the best tradition of Margaritaville liveaboard sailors.

“Attitude is the difference between ordeal and adventure.”

Bob Bitchin

Sure, you can choose to view obstacles and problems as something absolutely dreadful, an ordeal. Heck, I’m not perfect, so I’ll admit that’s my default reaction.

Or we can remind ourselves that everything has a potential upside, and activate that famous stoic resilience, and then look for that silver lining, that possible adventure. And keep reminding ourselves that every obstacle is a new opportunity.

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