The Obstacle is the Way

„The obstacle is the way“ by Ryan Holiday tries to give us a way out when we think there isn’t one.

This is the moment you were afraid of. You thought it might come to this but it’s worse than you’ve imagined it. There it is. The obstacle you believe you can’t move past.

          The obstacle is unique to each of us. Ryan Holiday explains the obstacles that elicit responses ranging from Fear, Frustration, Confusion, Depression, Anger…

          Evy Pompouras, former Secret Service Agent, on the other hand, tells us that a problem triggers one of three responses: fight, flight, or freeze. In her book, “Becoming bullet proof”, she explains each reaction in more detail. It basically comes down to these three or a variation of them.  

          It matters less the name we give to the way we react. What matters is how prepared are we when adversity strikes.

As Niccolo Machiavelli mentions in his “Il Principe”, it’s great to believe in favorable circumstances. However, we cannot rest on that idea alone. The best thing we can do is prepare instead of letting something else make that decision for us. We should make the necessary preparations before adversity hits us. When it does, we have a better chance of making it through alright.

It all depends on perception

Perception is how we see and understand what happens around us and our decision about the significance of those events.

Our perceptions can become a source of strength or of weakness.

“Nothing either good or bad but thinking makes it so” as Shakespeare puts it.

Through our perception, we decide the importance of an event in and on our lives.

Without us, there is no good, nor bad, but the only perception. In other words, we are complicit in the creation as well as the destruction of every one of our obstacles.


What not to do when adversity strikes?

When America was in the race to send the first men into space, they trained the astronauts in one skill more than the rest: the art of not panicking.

Panic throws reason out the window. The moment we panic, it’s the moment we start making mistakes. We override systems, disregard procedures, ignore rules, deviate from the plan.

“Emotional Intelligence” shows us that, in order to deal with other people, we have to first know ourselves.

In order to handle an obstacle situation, we must first know what type of response we usually indulge in. Are we a fight, flight, or freeze type of person? Once we know what type of response we have, we can begin to improve our chances by practicing. Learning a skill means just that: practice.

We can practice our responses in different situations. The only way to do that is to face obstacles head-on, regarding them as a teachable moment.


The best way to face an obstacle is to get moving. The initial shock has passed. You set your emotions aside. Now, look at the matter from another perspective.

Sometimes, we tend to imagine our problems bigger than they are.

One thing we can do is break it into more manageable pieces.

Coach Nick Saban of the University of Alabama football team puts it simply:

“Don’t think about winning the SEC Championship. Don’t think about the national championship. Think about what you need to do in this drill, on this play, at this moment. That’s the process.”

The thought of the end result can be daunting, at times. Instead, we should focus on taking one step after another and enjoying every minute of it.

Excellence is a matter of steps. Excelling at this one step, then another one, then another one.

It’s alright to keep in mind the end goal. However, we should make sure we concentrate on right now, this very moment, and how, by improving this very moment, ensures our reaching the top.

Prepare for none of it to work

We can:

  • Manage our perceptions
  • Direct our actions
  • Think clearly
  • Respond creatively

However, despite all that, there comes a time when none of our actions will work.

The only thing we cannot do is control the world around us. We might perceive things well, act accordingly and fail anyway.

One thing is clear: nothing and nobody should prevent us from trying.

Sometimes obstacles might turn out impossible. Some paths cannot be crossed. Sometimes, things are bigger than us.

That’s not necessarily a bad thing. We can turn an obstacle upside down, by using it as an opportunity to practice some other virtue or skill – even if it is just learning to accept that bad thing happen or simply practice humility.

Problems are a chance for us to do our best. No more, no less. We must be willing to roll the dice and lose. Prepare, at the end of the day, for none of it to work.

As Chris Voss, former FBI hostage negotiator tells us in his “Never split the difference” – be prepared to walk out of a deal if you believe it doesn’t suit you or bring you what you need.

We should do our best to prepare. We should focus on the step we are about to make, practice it until we get it done to perfection before we move on to the next. However, we should also be prepared to cut our losses and move on. Sometimes, it takes more courage to walk away than it does to stay.

Build your inner citadel

Will is our internal power that can never be affected by the outside world. However, it’s not something most of us are born with. The good news is that it can be cultivated and enforced.

We are not born with a perfect structure. We must build it and actively reinforce it.

During the good times, we strengthen ourselves and our bodies so that during the difficult times, we can depend on them.

We protect our inner fortress so it may protect us.

“The art of War”, written in the 6th century BC, attributed to Sun Tzu, a strategic general provides the answer.

The key to a good strategy is planning. The chances of success are increased exponentially for those, who sit down and make plans and think of possibilities of actions. For those, who are not in the habit of planning ahead, victory can be miles away. Take into consideration every possible course of action and the result shall be clear.

In order to get from one obstacle to another, we have to prepare ourselves. Practice without break. Just as athletes do in between competitions. In order to win a war, we have to practice during peacetime.

It’s nice to believe that we can escape problems, but the world doesn’t work that way. Instead of burying our heads in the sand, we should prepare ourselves for the moment adversity strikes. As the saying goes: we practice for the worst while we prepare for the best.

“The Obstacle is the way” is a compilation of stories, wrapped around a piece of advice. It’s not meant to wake us to reality but to prepare us for the moment reality strikes.

It’s a good tool under our belts and a good practice for those hard moments in everyone’s life. If not for the pieces of advice, at least for the stories of great men and women who came before us and dealt with obstacles that seemed impossible.

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