Lessons From Books: The Obstacle Is The Way

In the book, The Obstacle Is The Way, Ryan Holiday takes lessons from some of the most notable men and women throughout human history on how they overcame their specific obstacles and compiles them in one place. As the book title suggests, the book is about overcoming obstacles and Holiday believes we overcome obstacles through three critical steps: Perception, Action and The Will.

One thing that is stressed throughout the book is not to walk blindly through life. If you do, then you’ll be constantly thrown about. Instead, what you need are principles and frameworks that are specific to you so this can include working on a positive mindset, self-affirmations, set of reminders, principles to live your life by, being cool-headed and having self disciple like Rockefeller, building the habit of taking action and practicing to overcome your weak spots like Demosthenes, humility, endurance and compassionate of Lincoln, and so on.

By doing so, he shows what we require is a

Method and a framework for understanding, appreciating, and acting upon the obstacles life throws at us.

The following are lessons to help build that framework.


On Perception

Perception plays a key role in overcoming obstacles. Our perception can aid an obstacle in becoming an obstacle. Also, “through our perception of events, we are complicit in the creation—as well as the destruction—of every one of our obstacles.

There is bad perception and good perception. Bad perception comes from being emotional, subjective, and shortsighted. If you cannot perceive the obstacle in the correct manner, then overcoming them becomes difficult because your aim/method will be wrong. It’s not about the obstacle, it’s about our reaction and attitude towards it. A failure to one individual can be critical, but the same failure to another can propel them onwards because they perceived the failure correctly and didn’t add to it with their own emotions or attitudes. 

A good person dyes events with his own color…and turns whatever happens to his own benefit – Seneca

You can’t see the opportunity if you can’t control your emotions and are subjective and impulsive. Every situation is an opportunity to prove your worth, to better yourself, to practice virtue or discipline, but the right perception is required.

Desperation, despair, fear, powerlessness—these reactions are functions of our perceptions. You must realize: Nothing makes us feel this way; we choose to give in to such feelings.

Fear and panic are two emotions that breathe life into bad perception. If your decisions are rooted in fear or caused by panic, then you are most likely creating further obstacles.

The perceiving eye is weak; the observing eye is strong – Miyamoto Musashi

Practice objectivity when you can. Acknowledging an event happened is objective, believing that event was bad, is subjective. Besides, your problem isn’t unique. People have tackled the same problems for centuries, find examples of how people overcame your situation.

That we are scared of obstacles because our perspective is wrong—-that a simple shift in perspective can change our reaction entirely.

Have A Clear Vision

Work ethic combined with vision gets things done. Vision provides the aim, the target, and the work ethic provides the movement towards that target. Some people have poor vision because they believe in the obstacle more than in the goal. You are conceding to the obstacle before you even attempt to overcome it. We can relate vision to the importance of belief. You have to believe that you can overcome whatever obstacle is in front of you and achieve your goal. Once that is settled, then you can create a plan of action that achieves your goal.

Take Action

The right and effective actions are made up of deliberation, boldness, and persistence. The action is performed in the service of the whole. The whole is the goal. So, the small steps, movements, efforts, habits, what may seem like insignificant choice of discipline, all add up to the completion of the whole. It all moves you towards your goal.

A part of overcoming obstacles is ownership.

No excuses. No exceptions. No way around it.

No one is going to get rid of the obstacles for you. You have to do it yourself. This may require self-reflection and change of habits and mindset and/or making new habits, developing new skills, getting out of your comfort zone. Whatever it may be, the primary requirement is yourself and the actions or the inactions you commit. Make it happen; create the change. 

The start doesn’t matter. What matters is the momentum. So say yes and ask yourself: Could you be doing more?

On Persistence

Genius often really is just persistence in disguise.

Persistence is defined as a firm or obstinate continuance in a course of action in spite of difficulty or opposition. Life is hard. Achieving your goals is difficult. There are and will be many obstacles in your way. These are facts that you have to accept. Your first steps will not work. Accept that reality. Accept the reality that many failures await you. Persist towards your goals anyway.

Working at it works. It’s that simple.

A way to persist is by living in the moment and controlling what you can influence right at this moment, which are your actions. Don’t be overly concerned about the end goal. There is a lot of room between the start and the finish. If you’re constantly thinking about the finish, it’s easy to get discouraged when that line seems like it hasn’t moved. Instead, in order to persist, focus on the small multitude of steps you have to cover before you can get to that finish. Do the right thing, right now, in the present moment. Don’t worry about the rest. Just one clean movement after the other.

Excellence is a matter of steps.

Concentrate on making the tough choices, the hard decisions, ones that will bring long-term benefits, ones that sacrifice short-term pleasure.

The trick to forgetting the big picture is to look at everything close up – Chuck Palahniuk

Have Pride

It is cliche to say that you should try to do whatever job it is the best you can, but that really matters. Putting your best effort into what you’re doing, no matter how trivial, reinforces positive habits and mindset.

You are the sum of your actions.

These are the steps that will matter when you get a different opportunity. If you get into the bad habit of half-assed effort, then when you start your “dream” job, that habit will poison it.

But you, you’re so busy thinking about the future, you don’t take any pride in the tasks you’re given right now. You just phone it all in, cash your paycheck, and dream of some higher station in life. Or you think, This is just a job, it isn’t who I am, it doesn’t matter.


Be Pragmatic

We spend a lot of time thinking about how things are supposed to be, or what the rules say we should do. Trying to get it all perfect. We tell ourselves that we’ll get started once the conditions are right, or once we’re sure we can trust this or that. When, really, it’d be better to focus on making due with what we’ve got. On focusing on results instead of pretty methods.

A form of self-sabotage is this need to have perfect conditions. Instead, you have to find the way despite your conditions.

Think progress, not perfection. 

Find the best approach to get the desired results. It doesn’t matter if it isn’t the “right” way. The way is the one that produces results.

Have a strategic approach to your goals. Don’t just have a goal out in the future, instead, break it down into smaller and smaller steps. Steps that you can put into action and will help you make progress.

The process is about finishing. Finishing games. Finishing workouts. Finishing film sessions. Finishing drives. Finishing reps. Finishing plays. Finishing blocks. Finishing the smallest task you have right in front of you and finishing it well.

The root cause of our dissatisfaction and failure to achieve our goals is our attitude and approach. Don’t have this fixed mindset where if you fail once you just assume that you’re not good at it or this goal isn’t meant for you. Instead, assess your performance and failure and approach again with a slight tweak. View your approach as a hypothesis. If the hypothesis fails, you have to make adjustments to it and run the tests again.

On Will Power

Will power means to have the endurance for the long haul. Your will is under your control and you can apply it when the going gets tough, which it eventually will because life has many difficulties. You will fail many times at attempting your goal but to keep on trying, that’s what it means to have endurance. 

One way to strengthen your willpower is through physical exercise. To put your body through tough regimens that will cause you to question whether or not you want to do it again. Every time you can overcome such thoughts and feelings, it will strengthen your resolve. 

We craft our spiritual strength through physical exercise, and our physical hardness through mental practice […] Many (Ancient Philosophers) saw themselves as mental athletes—after all, the brain is a muscle like any other active tissue. It can be built up and toned through the right exercises. Over time, their muscle memory grew to the point that they could intuitively respond to every situation. Especially obstacles.

Perseverance is another aspect of willpower.

Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.

Staying power. It is by sticking your ass to the seat and not leaving until the work is done. It is the quality you need, along with discipline, to make progress in life. The ability to grind.

There are far more failures in the world because of a collapse of will than there will ever be from objectively conclusive external events.

Perspective Towards Life

Life is a process of breaking through these impediments—a series of fortified lines that we must break through.

Each time, you’ll learn something. Each time, you’ll develop strength, wisdom, and perspective. Each time, a little more of the competition falls away. Until all that is left is you: the best version of you.

Concentrate on making progress and not trying to hit the home run with each swing. The big swings and misses cause discouragement. Instead, live a purposeful life that consists of several small steps in the service of the whole.

Great Quotes:

What such a man needs is not courage but nerve control, cool-headedness. This he can get only by practice – Theodore Roosevelt

With the exercise of self-trust, new powers shall appear – Ralph Waldo Emerson

You must never lower yourself to being a person you don’t like – Henry Rollins

Death makes life purposeful.

Behind mountains are more mountains – Haitian proverb

Cheerfulness in all situations, especially the bad ones.

To be great at something takes practice. Obstacles and adversity are no different.

Action, Action, Action! – Demosthenes

My formula for greatness in human being is amor fati: that one wants nothing to be different, not forward, not backward, not in all eternity. Not merely bear what is necessary, still less conceal it…but love it – Nietzsche