The Obstacle is the Way

The Obstacle is the Way

The Obstacle is the Way

A colleague of mine sent me a book summary recommendation that is spot on for the times.  It is a quick read and an excellent reminder of the mindset we could all benefit from right now.

The Obstacle is the Way

by Ryan Holiday

A book summary provided by the book summary service,

Every obstacle we face on our path to greatness is unique. But our responses to them are the same.

Fear. Frustration. Confusion. Helplessness. Depression. Anger.

Why is it that some people get paralyzed by these circumstances and emotions, and others seem to answer the call and deal with life head on – and sometimes, to our amazement, even seem to enjoy it?

That’s what we’ll cover in Ryan Holiday’s The Obstacle Is The Way. Overcoming obstacles, Holiday tells us, is a discipline of three critical steps.

Let’s get started.

Part I: Perception

Perception is how we see and understand what occurs around us. It’s also who we decide what those events mean to us.

Our perceptions can either be a source of weakness or a source of strength. If we are emotional, subjective and shortsighted, they can be a weakness. If we can learn to limit our passions and their controls over our lives, our perceptions can become a strength.

When we are faced with an seemingly insurmountable obstacle, we must try to do the following things.

Be objective

The events in our lives – even the obstacles – are neither good or bad. They just are. We are the ones that add meaning to them. We have the choice to determine if the story we make up about an event is positive or negative.

Our tendency, especially when faced with adversity, it to choose a negative narrative. What if, instead, we chose to tell ourselves a positive story about the event?

Control emotions and keep an even keel

The emotions you feel about an event in your life are determined by the story you tell yourself about the event.

So it follows that you can also choose to keep an even keel even in the face of the most difficult of circumstances.

When panic (or any other negative emotion arises), you can feel the emotion, let it pass, and then get back to work.

Choose to see the good in a situation

Once you’ve got your emotions under control, you can decide to see the good in a situation.

Just like you can make up a negative story, you can make up a positive story. One that moves you towards action instead of despair. Choose a narrative that empowers you rather than debilitates you.

Place things in perspective

As Holiday points out, perspective has two definitions.

The first is context – a sense of the larger picture of the world, not just what is immediately in front of us. The second is framing – an individual’s unique way of looking at the world, a way that interprets its events.

Both of them matter. For instance, George Clooney was rejected by Hollywood for years, and his perspective was that the system was broken and they couldn’t see how talented he really was.

However, when he changed his perspective to one where the directors had a problem they needed solved – they were hoping the next person to walk in would be the right somebody – Clooney realized that he was the answer to their prayers, not the other way around.

The rest, as they say, is history. Your perspective matters.

Live in the present moment

It doesn’t matter whether or not you are in good economy or a bad one. Or whether or not a huge obstacle is lurking right around the corner. What matters no, is right now.

We all spend a good portion of our lives thinking about the past and the future, much to the detriment of dealing with whatever is right in front of us.

You can’t deal properly with your obstacles if you are only thinking about what should have been, and what might yet come.

This isn’t touchy feely philosophical stuff – the only thing you truly have control over is what you do right now.

Focus on what can be controlled

What is in your control?

Your emotions, judgments, creativity, attitude, perspective, desires, decisions and your determination.

Focussing exclusively on what is in our power magnifies and enhances our power. Any ounce of energy directed at things we can’t actually control is wasted.

Part II: Action

Now that we’ve got our perspective and emotions under control, it’s time to take action.

But not all action is created equal. In order to be effective we need directed action – everything done in service of the whole.

We dismantle our obstacles piece by piece, with courage and creativity. We greet our obstacles with energy, persistence, a deliberate process, iteration, pragmatism and a strategic vision.

Get moving

We often get stuck when facing obstacles. Sometimes taking action seems too risky. As a result, we do nothing.

The only rule in taking action is to stay moving, always.

If you want to create momentum, you need to do it yourself. Now.

Practice Persistence

In 1878, Thomas Edison wasn’t the only person who was working on incandescent lights. But he was the only person who was willing to test six thousand different filaments – inching closer to the finish line with every test.

As Holiday points out, genius is often just persistence in disguise.

Nikola Tesla spent a year in Edison’s lab, and once said that if Edison needed to find a needle in a haystack, he would simply “examine straw after straw until he found the object of his search.”


When you take action, you must keep in mind that action and failure are two sides to the same coin. You don’t get one without getting the other.

When you do fail (and you will), ask yourself what went wrong and what you could improve for the next time.

Failure is often the source of your biggest breakthroughs.

As Holiday points out, great entrepreneurs are never wedded to a position, never afraid to lose a little of their investment, and never bitter or embarrassed.

They slip a thousand times. And if they fall, they always get back up.

Follow the process

Nick Saban – the coach of the powerhouse University of Alabama football team, teaches his team “The Process.”

Here’s how he puts it:

Don’t think about winning the SEC Championship. Don’t think about the national championship. Think about what you needed to do in this drill, on this play, in this moment. That’s the process. Let’s think about what we can do today, the task at hand.”

Basically, focus only on what you need to do right now, and do it well. Then move on to the next thing.

The process is about finishing. Whatever you are doing right now, finish. Finish your workout. Finish games. Finish your inbox. Finish the smallest task you have in front of you right now.

Don’t worry about what will happen later, or what has already happened.

Do your job, do it right

Sir Henry Royce puts it perfectly when he says “Whatever is rightly done, however humble, is noble.”

Whatever tasks we are faced with – some prestigious and some onerous – we must respond with hard work, honesty and helping others as best we can.

What’s right is what works

The other side to the “do it right” coin is that we need to get the job done, and being a pragmatist helps.

Holiday tells the story of Sam Zemurray, who was battling for a plot of land with United Fruit, a giant company many times his size. Two separate people claimed ownership of the land. United’s response was to bring a large crew of expensive lawyers to figure out who rightfully owned the land. Zemurray simply bought the land twice – once from both parties who claimed ownership.

Don’t worry about what your family, friends, and society say is the right way to do things. Worry about getting the job done.

Use obstacles against themselves

As Holiday points out, Ghandi didn’t fight for independence for India. British Empire did all of the fighting, and all of the losing.

Ghandi realized that he – and the Indian people – had no chance of victory by meeting force with force. Instead, he peacefully violated British rule, exaggerating his weakness in the process. The British Army had two choices – to enforce a bankrupt policy or abdicate. Ghandi had neutralized their military advantage by making its very use counterproductive.

Instead of fighting obstacles, find a means of making the obstacles beat themselves.

Channel your energy

Arthur Ashe battled segregation in the 1950s and 60s when we was on the rise in the tennis world. His father taught him to mask his emotions and feelings on the court as a defence mechanism. Instead, his father coached him, he should channel his energy into his shots.

His style was to be “physically loose and mentally tight.”

Obstacles and adversity can harden you, or it can loosen you up and make you better. Put your frustrations to good use.

Prepare for none of it to work

You can manage your perceptions and direct your action. What we can’t do is control the world around us. It’s possible that even after doing all of the right things, you’ll still fail.

Preparing yourself for that possibility gives you the freedom to act with boldness and courage.

Part III: Will

Will is our internal power. It can never be affected by the outside world, because it is completely within our control.

Will is not how badly we want something. But will is much more about surrender than strength. It is more like “God willing” then “the will to win.”

When we are placed into a situation that seems impossible to fix, we can decide to view it as a learning experience or a chance to help others. That’s will power.

The discipline of will

Most people don’t know that Abraham Lincoln suffered from crippling depression his entire life. It nearly drove him to suicide, twice.

But because Lincoln defined his life by enduring and overcoming great difficulties, he was able to find meaning in his suffering. For him, he was destined to suffer these things so that they could forge him into the man he needed to become.

It should be no surprise that “this too shall pass” was his favorite saying.

Build your inner Citadel

It’s possible to face every external adversity you could conceivably imagine, and never break down. But that capacity needs to be built. Use whatever adversity you are facing right now to prepare you for larger and scarier challenges you’ll face later.

Anticipation (thinking negatively)

These days, it’s fashionable in business to hold a pre-mortem. Basically, you think about all of the things that could go wrong with an initiative in the hopes that you solve most or all all of them before they happen.

This serves two purposes. First, it enables you to avoid some of the things that you can easily prevent. Second, it ensures that you are infrequently surprised by negative events.

Things will always go wrong. Preparing for how you will react in those cases is critical for your success.

The art of acquiescence

This is the art of accepting reality as it is. You don’t have to like or enjoy the treatment, by you know that denying it only delays the cure.

Quickly come to terms with the reality of your situation so you can get on doing the things you can actually control.

Love everything that happens – Amor Fati

When Thomas Edison was 67, a great fire broke out at his lab and factory. As he was looking on at the devastation with the hundreds of onlookers, he told his son to “Go get your mother and all her friends. They’ll never see a fire like this again.”

By loving everything that happens – Amor Fati – we turn what we must do into what we get to do.

The Stoics commanded themselves “Cheerfulness in all situations, especially the bad ones.”


As Holiday points out, there are more failures in the world due to a collapse of will than there will ever be from objectively conclusive external events.

Antonio Pigafetta was the assistant to Magellan on his trip around the world. When he reflected on what his most admirable skill was, he said that the secret to Magellan’s success was his ability to endure hunger better than the other men.

Meditate on your mortality

Nobody gets out of life alive. There is a very short list of obstacles that cannot be overcome, and death comes in a #1.

When we meditate on our mortality, all of a sudden life seems very short, and we are faced with a choice.

We can live the rest of our life using the power of the principles Holiday has taught us, or we can live the rest of our life like we’ve always done, and keep getting the results we’ve always got.

The choice is yours – decide today.