The Obstacle is the Way by Ryan Holiday

Feeling overwhelmed, pressured, rushed, my client had demanded that the task be completed straight away, while jabbing comments about it maybe being a mistake they chose my company for their services.  The task was complex and quite unorthodox to be dealt with so quickly.  That’s when I was reminded that this situation in front of me, was my obstacle.  I was at the beginning, I had no choice but get to the end, and this dataset to be created was preventing me from passing.  I began to break each of the tasks into smaller pieces, looking at them without the narrative of being “complex”, rather breaking them smaller and smaller until they were simple.  Just a bit after 5pm, I sent the e-mail to the client that I had completed the task.

“The impediment to action advances action. What stands in the way becomes the way.” — Marcus Aurelius

Ryan Holiday takes the ancient wisdom of Stoicism to write the book The Obstacle is the Way, a practical philosophy to approaching life.  As you may guess from the title of the book, it is about turning what the world sees as obstacles, as the path that you should take.  The example mentioned above is just one of the many times I have referenced to this very draft of this article to get perspective of my difficult situations.

The strategies and philosophy Ryan shares with us can have massive consequences in your life.  For every single one of us, life is gonna throw us shit.  No one has it honky dory — no matter what your Instagram feed looks like.  You have heard it many times, those who are at the top always talk about the obstacles and failures they had to overcome to get there.  The key is that they overcame them.

“That thing you dread or secret thing you don’t want to happen, what if it wasn’t so bad?  What if inside it or embedded in it is or inherent in it was certain benefits.  Benefits only for you.  What would you do?  Probably what most people do, nothing.”

The book is broken into three parts, 1) Perception, 2) Action, 3) Will.

“Objective judgment, now at this very moment.
Unselfish action, now at this very moment.
Willing acceptance—now at this very moment—of all external events.
That’s all you need.


In this first section, we learn that there is the obstacle and then there is how we think about it, they are separate. Our perceptions create our reality, it is not what happens that affects us, but the narrative and the context that is around what happens that does.  Often the obstacle does not really exist, but merely our thoughts and feelings that we bring to the situation that creates the obstacle.  How much does hate, fear, anxiety, paralyze us? What we must realize is that “Nothing makes us feel this way; we choose to give in to such feelings.”

What we need to do is steady our nerve, stay in control of your emotions.  Yes the obstacles and feelings are overwhelming, so it is with Kobe Bryant when the clock is running down and he’s got to make a shot over two defenders.  But when you are able to steady your nerve, “then nothing really did “happen”—our perception [makes] sure [it’s] nothing of consequence.”

“The observing eye sees events, clear of distractions, exaggerations, and misperceptions. The perceiving eye sees “insurmountable obstacles” or “major setbacks” or even just “issues.” It brings its own issues to the fight. The former is helpful, the latter is not.” — Miyamoto Musashi

We need to recognize what happens as what they actually are.  There are many ways to look at a situation productively, often some tactics are better than others.

Is it in your control?  Can you even do anything about it?  If not, then carry on.  Should what you’re going through be a surprise?  Is the world out to get you, or is it a natural resistance that would face anyone on your journey?  If it is, face it bravely as if the obstacle has been fated to your path.   Is it possible to defeat this obstacle for someone else?  If yes, then why not you?

On the other side of it, you will be rewarded with lessons learned, a stronger will, and confidence from experience. This holds one of the most important keys to your perception, where it’s not about what you see as the obstacle, but what you stand to gain on the other side of the obstacle. Obstacles are opportunities for you to grow, to achieve, to better yourself.

“The struggle against an obstacle inevitably propels the fighter to a new level of functioning. The extent of the struggle determines the extent of the growth. The obstacle is an advantage, not adversity. The enemy is any perception that prevents us from seeing this.”


In this section, we learn that not any action will do.  Controlled, well thought out, calm, creative action is the necessary types to conquer what stands in the way.  Often rather than fighting with a strategy, we relentlessly start swinging for the ropes.  This is what separates the Hollyfields from the backyard brawlers.

“Action is commonplace, right action is not. As a discipline, it’s not any kind of action that will do, but directed action.”

The perfect time for action is now.  Are the circumstances desirable?  They never are, for any of us.  People have gotten over way more than you and I, come from behind and had way bigger obstacles.  Racial discrimination, sickness, poverty, homelessness, illiteracy.  Yet they didn’t waste time in waiting for the perfect opportunity to come up, those don’t exist.  The perfect opportunities come to those who put in the work.  So just start, every accomplishment has the first step in common — the first step.

When you got the ball rolling, you’ve got to keep at it, cause The Dip and The Resistance are coming for you.  But a dogged determination is what is going to get you through it. Be persistent. Repeat the process, keep trying, test new theories, poke different spots and attack different angles.  Sometimes there won’t be much of a strategy behind it, except doing it one at a time.  Sounds simple, but it’s not easy.

“Edison, was not the only one at the time trying to invent a light bulb.  However Edison was the only one who was willing to test six thousand different types of filaments until he found the right one.”

While you are trying, practicing, applying, moving, executing, always gather feedback.  Remember, creativity and strategy are necessary.  We are not just trying the same method over and over and hoping for a different outcome.  We will try, see what happens, and then form a new hypothesis and try something different.  The strategy will come, and it will change, and evolve.  Tech startups have the concept of the MVP, minimum viable product.  They put out their product with minimal features, push it to a group of small customers and then listen and observe.  They can quickly push out new features and see how the customers react.  This allows them to iterate, remain flexible, and be agile.

Now that you have calmed your nerves, controlled your emotions, and can see the obstacle objectively, you will be able to see the situation for what it is.  Most obstacles you will come across, will only have a handful of variables to act against. Strategize your countermoves.

“Remember the first time you saw a complicated algebra equation? It was a jumble of symbols and unknowns. But then you stopped, took a deep breath, and broke it down. You isolated the variables, solved for them, and all that was left was the answer.”

After all is said and done, you have to be prepared that your actions come up empty.  You can think clearly, have dogged determination and execute, but sometimes it won’t be enough.  Perception and action is within your control, the rest of the world is not.  This is not failure, you are still able to turn the obstacle into an advantage.

“… simply by using it as an opportunity to practice some other virtue or skill—even if it is just learning to accept that bad things happen, or practicing humility.  It’s an infinitely elastic formula: In every situation, that which blocks our path actually presents a new path with a new part of us.”


The will is what’s left after perception and action.  External circumstances will influence my perceptions and my actions, but the will is the foundation which stands, or falls.  You choose the strength of your foundation, by choosing to build it up.  The will is forged by overcoming obstacles, and making conscious choices to be work it, no one is born with it.

A three step process for dealing with each obstacle and situation and strengthening your will is to i) Think Negatively, ii) Art of Acquiescence, and iii) Amor Fati.

“Nothing happens to the wise man against his expectation.” — Seneca

To think negatively is to anticipate the worst situations that could come.  You should not be caught off guard when life hands you shit.  Things will always go wrong, but if this comes as a surprise each and every time you are going to be set up for failure.  Set yourself up for success, by premeditating on potential obstacles.   For your current situation, be an optimist.  But when it comes to the future, be a pessimist, so that you are prepared for the worst of circumstances, so you are prepared with strategies in place to deal with them.

Accept whatever circumstances, and whatever troubles may come.  In whatever situation, no matter how bad it might get, these are all external circumstances.  Do not complain about it being hard for you, or talk about the way that it should be or should’ve happened.  You need to clear your mind, by accepting it.  Leave the negative thoughts behind, and focus on what you actually need to do.

After you’ve anticipated the obstacles and aren’t surprised by them, and have accepted them, the next level is to love it.  If an obstacle arises, it was meant to be there for you.  It may just be good that you have accepted it, but to love it is to fully embrace it and respect the obstacle for what it is, and what’s on the other side of it.  We have to love it because we know what the outcome will be on the other side of it.  We have to love it because it is the only path to greatness.

Start it over

After preparing your perceptions, executing effective actions, and exercising your will, just get ready to do it all over again.

“One does not overcome an obstacle to enter the land of no obstacles.”