The Obstacle is the Way – Turn Your Trials and Challenges Into Triumph (Ryan Holiday The Obstacle is the Way Overview)

Siim Land

How are you dealing with the challenges and impediments of your life? Do you crumble after reaching the wall or will you climb over it, making your failures but mere stepping stones for your successes? That’s the theme of Ryan Holiday’s book The Obstacle is the Way The Timeless Art of Turning Trials Into Triumph.

Ancient Stoicism in a Modern Setting

The title is based on one of the most renown stoic philosopher-kings of the Roman Empire Marcus Aurelius who wrote in his personal Meditations-diary these lines: “The impediment to action advances action. What stands in the way becomes the way.”

The Obstacle Is the Way Marcus Aurelius
The Obstacle Is the Way Marcus Aurelius

The main idea of the book [Ryan Holiday’s] is that obstacles don’t stop success but actually create it. That doesn’t go to say that failures and impediments won’t cut you down – they will if you give into them. It all depends on how you perceive your situation and how you CHOOSE to respond to it.

The book is built around three disciplines:

  • Perception – how you choose to see and think about the situation
  • Action – how you choose to act in response to it
  • Will – how you choose to adjust your focus and persist in dealing with adversity

Now, I’ll go through them one by one.

The Discipline of Perception

Perception is the way we see and interpret the situation. It’s how we derive meaning from what happens to us. This is so important to remember because how we perceive outside events literally dictates our internal experience.

William Shakespeare said: Nothing is neither good or bad but thinking makes it so.” There is the event itself and the story we tell ourselves about what it means.

The discipline of perception involves:

  • Looking at the event objectively
  • Controlling your emotions
  • Choosing to see the good in any situation
  • Steadying your nerves
  • Ignoring what others see as disturbing or limiting
  • Placing things in a larger perspective
  • Reverting to the present moment
  • Focusing on what can be controlled

Perception has two components:

  • Context: the bigger picture of the world, not just what’s immediately in front of us
  • Framing: your individual perspective of the situation – the way you perceive it

Seeing the opportunity for triumph in obstacles requires self-discipline, BUT, first-and-foremost it’s a matter of logic and meta-awareness. If you’re aware enough to recognize yourself in the midst of chaos and to not be overtaken by your emotions, then acting in search of the best solution, despite the turmoil, is the natural thing to do.

Controlling your perception is critical for creating your entire life. Where the head goes, the body follows. Perception precedes action.

The Discipline of Action

At the end of the day, it doesn’t matter how we think or how many great opportunities we can see or conceive of unless we actually act upon them.

But, it’s not only about taking action but taking the right action. Actions have to be directed in the best interest of our goals.

If you’ve unraveled the situation as you choose with your perception, peeled through it with the sword of your consciousness, then you’ve identified the right course of action. All that’s left to do now is act.

What you possess in approaching any challenge and actions is:

  • energy
  • persistence
  • a coherent and deliberate process
  • iteration and resilience
  • pragmatism
  • strategic vision
  • craftiness and savvy
  • and an eye for opportunity and pivotal moments

Where most people fail is waiting for the right moment to act. What I’ve learned along my journey is that: “It doesn’t matter where you are going, as long as you keep going.” As long as you keep moving forward, magical things will begin to happen. You’ll figure it out along the way.

You could spend an eternity waiting for the perfect thing or perfect time to hit you, but the reality is nothing is perfectly perfect. The Stoics say: “Don’t go expecting Plato’s Republic.” There will always be something to improve and work on. You’ll only remain a diamond in the rough but what you can do right away is start something.

The second component to taking massive action in life is consistency. You have to stay persistent with what you do because Rome wasn’t built overnight.

This means doing something daily that would move you closer to the success you seek and doing it with a yearning heart. No great achievement was built in a flash. What lies beneath the surface façade of the accomplishment – of Michal Jordan’s godlike skills, of da Vinci’s genius – are thousands of hours of consistent practice.

What’s more, you can’t be discouraged by the failures nor the haters. It’s okay to be discouraged, but it’s not okay to quit. UNLESS your priorities completely change. Don’t do certain things just because you don’t want to look like a loser.

If something’s not moving you closer to your goals then drop it. BUT, if is a quintessential component to your meta-achievement and legacy, then you have to plant your feet to the ground and keep going.

Your vision needs to be stronger than the desire to quit. I haven’t even preconceived the idea of ever quitting what I do because I’m clear on what I want. It may not be certain how I’m going to get there, but that’s the least of my worries. You have to trust the process and focus on doing your thing as well as you can.

The Discipline of Will

There is something all men possess that enables them to surmount any obstacle on their way and go through hell and back without giving a damn.

It’s our WILL.

Will is our inner source of strength that could never be affected by the outside world. It’s a faculty of push comes to shove that gives you the assertiveness of going to places unwary minds could never go and stay persistent on your path to glory.

This is the third part that makes you mentally prepare for the obstacles that will rise up and stand undisturbed in front of them.

Developing an iron will entail you building an inner citadel inside your mind that would not fall under siege. This inner strength needs to be built and cultivated like you would train your body. A warrior is a warrior of mind first and foremost.

Your willpower can be built by facing challenges that would force you to get out of your comfort zone whether physically or mentally, but also by facing emotional turmoil and adversity. The key is to practice staying undisturbed by detaching yourself from the situation.

Expecting shit to happen is another strategy. If you already know that there will be impediments and that they will be difficult to surmount, you can already pre-emptively prepare your mind for the hard effort.

Concluding Remarks

“The impediment to action advances action, what stands in the way becomes the way.” What’s funny is that once you adopt this type of thinking – of not seeing obstacles as unfairness but as opportunities for greater success – your entire perspective on life changes. You first become immune to the misfortune that may happen to you but you will also increase your default state of happiness.

What’s more, you’ll climb down your ivory tower and actually start doing what you want to accomplish. You’ll begin to define yourself through the actions you take to overcome obstacles and difficulties, not by the mere words and thoughts you use to describe yourself currently.

The Obstacle is the Way is a must-read for everyone wanting to live extraordinarily by achieving their success in spite of resistance or adversity. Check out my other book reviews, subscribe to my YouTube channel and join my Facebook group to get more of these life-altering paradigm shifts.

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The Obstacle Is the Way Ryan Holiday Overview by Siim Land
The Obstacle Is the Way Ryan Holiday Overview by Siim Land