The Art of Taking Action

How to Act in the Face of Adversity and Win Big

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“Action is commonplace, right action is not.” — Ryan Holiday

When confronted with an obstacle, we often choose to ignore it, to wait, or to simply claim we’re overwhelmed. But the only thing that will solve an issue is action.

In the face of adversity, Ryan Holiday points out in his book The Obstacle Is The Way, we need to cultivate energy, persistence, a deliberate process, resilience, pragmatism, strategic vision, craftiness, and an eye for opportunity.

Before right action can take place we first need to objectively judge a situation, and we should generally strive to cultivate an unbendable will, an Inner Citadel. I have written about these ideas, both concerning our internal response to events, in a recent article.

Here I want to fill in the gap and focus on how to act when we encounter adversity.

The key here is right action, not simply action. Or worst of all, reaction.

Right action can take an obstacle and turn it on it’s head, seizing it as an opportunity for growth and success.

There are two components to right action: Doing things right, and doing the right thing. These concepts overlap in many respects, but let’s try and look at them in turn.

Doing Things Right

Adversity often hits us in unexpected situations, otherwise we might have avoided it altogether. And it is very easy to be paralyzed by the unexpected.

One essential habit to develop in times of crisis is to just get moving.

It’s easy to tell ourselves that the circumstances aren’t quite right yet and we’re still waiting for them to change. But guess what? Chances are they won’t change. It’s really just an excuse for inaction.

Getting started is the most important part, even if the circumstances suck. The momentum built from the action will help correct for the non-ideal circumstances later.

“The best men are not those who have waited for chances, but who have taken them; besieged chance, conquered the chance, and made chance the servitor.”
— E. H. Chapin

Deliberation before taking action is valuable and advisable in many situations, but can also hinder crucial momentum. Besides, if you have worked on your mental response to adversity you can much more quickly and accurately assess a situation and start acting, rather than emotionally reacting. We don’t want to act out. We want to act.

People who take the initiative usually win, even if the conditions weren’t perfect or their actions not completely refined. They can course-correct before others even start.

In general we should aim for progress, not perfection. It is very easy to spend too much time looking for the perfect solution and as a result passing up on many good ones that are right in front of us.

Iteration is key! We have to do, fail, learn from failure, do again, repeat, until we reach the desired outcome. The crucial part is to not blindly iterate, but to evaluate after each failure exactly what went wrong and improve from there.

“Failure puts you in corners you have to think your way out of. It is a source of breakthroughs. […] Like any good school, learning from failure isn’t free. The tuition is paid in discomfort or loss and having to start over.”
— Ryan Holiday

What we want is temporary, anticipated failure, NOT catastrophic and permanent failure. Again, the chance of this kind of failure depends largely on how objectively we were able to perceive the situation. Techniques such as premeditatio malorum and negative visualizations outlined in my previous article also help with anticipating and being prepared for failure.

If we follow these ideas, the circumstances we find ourselves in actually don’t matter all that much.

“External factors influence the path, but not the direction: forward.”
— Ryan Holiday

Many people get very hung up on external rules or their environment, get angry at them, and complain. Obviously to no avail.

Instead we should just calmly take what we are given, subtly subverting and undermining any circumstances that hinder us, and manipulate them to our advantage.

Doing The Right Thing

So now we got things moving. We decided to act and are gathering momentum. But how do we make sure that we do the right thing?

A key here is to establish a process-oriented mindset. Instead of always thinking of the big goals and challenges, we should break them down and then simply focus on and do what is needed right now. Then move on to the next thing.

Focusing on doing each small thing well, without the distraction of worrying about the whole, will give us a much clearer idea of what needs to be done now at this very moment. Besides, it also serves the purposes of giving us a more frequent sense of progress and accomplishment, fuelling our motivation and momentum. Following this process of small steps, the whole will automatically take care of itself.

When done right, even the most daunting and complex task becomes manageable.

This is wonderfully illustrated by a story Holiday tells in his book.

James Pollard Espy, one of the founding fathers of modern meteorology whose theories became the basis for scientific weather forecasting actually couldn’t read until the age of 18. By chance he attended a speech by famous orator Henry Clay and was incredibly impressed, but couldn’t find the courage to speak to Clay. One of his friends shouted “He wants to be like you, even though he can’t read.”

Clay’s response was genius in its simplicity. He took a poster that had his name written on it, and pointed at the letter “A”. Turning to Espy he said “You see that, boy? That’s an A. Now, you’ve only got 25 more letters to go.”

This is a process-oriented mindset in action. The big task of learning to read got broken down into manageable goals of learning a single letter at a time. Espy took the lesson to heart, and a year later entered college.


Another central point about right action is wonderfully summarized in one of my favorite quotes.

“How you do anything is how you do everything.”
— Ryan Holiday

Yes, this might be a bit of an oversimplification, but living by this maxim is the surest way on the path towards right action.

Whatever we do matters, so we might as well do it as good as possible and with pride. Even the small things, or things we do not enjoy but that have to be done, should be approached with honesty, our full attention, and a desire to help others without losing sight of our own goals.

Ultimately, the right action is the one that works. Sometimes we do it one way, sometimes another. Whichever way leads to the desired result is the correct one, not the one some arbitrary rules or our own habits and prejudices prescribe.

“Pragmatism is not so much realism as flexibility. […] Sometimes the longest way around is the shortest way home.”
— Ryan Holiday

When our original plan didn’t work out it often helps to take a step back and attack the obstacle not head on, but from an unusual angle.

This is in many cases the key to expert performance. Experts have developed such good mental representations of their particular task that they instinctively see the way around the problem, solving it in a smart way, not a hard way.

Facing adversity helps us develop this kind of view. It’s an opportunity, not a calamity.


Seeing each obstacle that presents itself not as an annoyance or disaster, but instead as a chance for unusual success and big victory can completely transform how you approach life.

“Be fearful when others are greedy and greedy when others are fearful.”
— Warren Buffet

John D. Rockefeller started his career in 1855, just before the Great Depression. While everyone else panicked, he stayed calm and made a fortune. The greater the chaos, the calmer he would be, and the more decisively he would act.

What obstacle or crisis are you facing that can be overturned? Whatever it is, by acting swiftly and with determination you might be able to transform it into a huge opportunity for success.