The Obstacle Becomes The Way

April 1, 2009

The Stoics had an exercise called Turning the Obstacle Upside Down. What they meant to do was make it impossible to ever not practice the art of philosophy. Because if you can properly turn a problem upside down, bad is constantly a new source of good.

Suppose for a second that you are trying to help someone and they respond by being surly or unwilling to cooperate. Instead of making your life more difficult, the exercise says, they’re actually directing you towards new virtues; for example, patience or understanding. Or, if something important is stolen or lost; a chance to be less dependent on material things. Marcus Aurelius described it like this: “The impediment to action advances action. What stands in the way becomes the way.”

Does this sound familiar? It should because it is the same thinking behind Obama’s “teachable moments.” Right before the election, Joe Klein asked Obama how he’d made his decision to respond to the Reverend Wright scandal. He said something like ‘when the story broke I realized the best thing to do wasn’t damage control, it was to speak to Americans like adults.’ And he what he ended up doing was turning a negative situation into the perfect platform for his landmark speech about race.

Remember that the common refrain about entrepreneurs is that they take advantage of opportunities. Well, this is something much different. The Reverend Wright scandal, the Special Olympics gaffe, a frustrating case where your help goes unappreciated, none of those are “opportunities” in the normal sense of the word. In fact, they are the opposite. They are obstacles. What a hustler does, or what a Stoic does is turn the obstacle into an opportunity.

Ryan Holiday

I'm a strategist for bestselling authors and billion dollar brands like American Apparel, Tucker Max and Robert Greene. My work has been used as case studies by Twitter, YouTube and Google and has been written about in AdAge, the New York Times, Gawker and Fast Company.

10 responses to The Obstacle Becomes The Way

  1. I think Pringles’ initial intention was to make tennis balls. But on the day that the rubber was supposed to show up, a big truckload of potatoes arrived. But Pringles was a laid-back company. They said “Fuck it. Cut ’em up.”

  2. francisco,

    Pretty sure that’s just a Mitch Hedberg joke.

  3. Believe me, he knows that. I gave him a Mitch Hedberg cd in 2001.

    His quotation is inspired.

  4. So I was driving home the other day to my new apartment and I made a wrong turn, at first I was annoyed, then I realized that this was just an opportunity for me to learn a new route home.

  5. I’ve noticed recently that a few things that I was “forced” into turned out to be just what I needed – I’m trying to train myself to accept certain things that I think I don’t want. They may look like something to avoid at first but after the fact they turn out to be opportunities rather than a waste of time.

  6. Last month American Airlines lost my suitcase and £500 worth of stuff on a domestic flight, while I was visiting USA…

    There’s no chance I’m getting that stuff back, and it looks like I’m not likely to get any compensation from them either!

    All my friends said, wow, how unlucky for you, that’s awful!

    For me, it was one of the most liberating experiences imaginable!

  7. the more I learn about stoicism, the more I realze that obstacle do shape your life, and attitude. More people need to realize this basic concept

  8. A slight variation of Tim Ferris’s quote: “What we fear doing most is usually what we most need to do”

  9. It is indeed great to hear that within the negative experience of life lays the seed for a much better positive future. The very thought can help us going – and our interpretation gives us valuable lesson to make things better for future.
    Thanks again,

  10. It’s great to see this article has morphed into a book I can now give to others. Keep it up man, you’re an inspiring soul.