The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday

Reading Time: 6 minutes


A practical and actionable philosophy on how to perceive, act, and thrive in an uncertain and changing world. Leveraging the wisdom of the Stoics, Holiday explains how we can deliberately improve the way we perceive the world and find the opportunities in the obstacles we face.

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Key Takeaways

You have a choice

“Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?”

Are obstacles going to stop you from getting where you want to be?


“We blame our bosses, the economy, our politicians, other people, or we write ourselves off as failures or our goals as impossible. When really only one thing is at fault: our attitude and approach.”

Stop blaming others for our circumstances. Look inward. Otherwise, your non-acceptance of personal responsibility and tendency to blame others can lead to bad outcomes, like a failed relationship. What can you change about your attitude and approach? 

The modern challenge

“Instead of opposing enemies, we have internal tension. We have professional frustration. We have unmet expectations. We have learned helplessness. And we still have the same overwhelming emotions humans have always had: grief, pain, loss.”

Most of us are no longer fighting in tribes or wars for our survival. Yet, despite the comforts of the modern world, we have still found ways to have a wealth of problems and frustrations.


“WHAT IS PERCEPTION? It’s how we see and understand what occurs around us—and what we decide those events will mean. Our perceptions can be a source of strength or of great weakness. If we are emotional, subjective and shortsighted, we only add to our troubles. To prevent becoming overwhelmed by the world around us, we must, as the ancients practiced, learn how to limit our passions and their control over our lives.”

“Our perceptions are the thing that we’re in complete control of. They can throw us in jail, label us, deprive us of our possessions, but they’ll never control our thoughts, our beliefs, our reactions.”

You control your perception of things. No matter what circumstance you face, remember this power.

“There is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means. That’s a thought that changes everything, doesn’t it?”

The story you tell yourself about the events in your life is what matters. How can you turn your story from one of disempowerment to one of empowerment?

Focus on what you can control

“Focusing exclusively on what is in our power magnifies and enhances our power. But every ounce of energy directed at things we can’t actually influence is wasted—self-indulgent and self-destructive. So much power—ours, and other people’s—is frittered away in this manner. To see an obstacle as a challenge, to make the best of it anyway, that is also a choice—a choice that is up to us.”

Don’t waste energy on things outside of your control. Focus on what you can do to better your situation, and it will eventually improve.

Be present

“You’ll find the method that works best for you, but there are many things that can pull you into the present moment: Strenuous exercise. Unplugging. A walk in the park. Meditation. Getting a dog—they’re a constant reminder of how pleasant the present is.”

The present moment is where you can change things. It’s the here and now that we often forget. There are many ways to tap into the present moment, and it’s your job to figure out the methods that work best for you.


“An entrepreneur is someone with faith in their ability to make something where there was nothing before. To them, the idea that no one has ever done this or that is a good thing. When given an unfair task, some rightly see it as a chance to test what they’re made of—to give it all they’ve got, knowing full well how difficult it will be to win. They see it as an opportunity because it is often in that desperate nothing-to-lose state that we are our most creative. Our best ideas come from there, where obstacles illuminate new options.”

Entrepreneurship is a mindset. It’s about having the courage and belief that you can create something that did not exist before. It’s knowing that the path ahead will be incredibly difficult.


“Action requires courage, not brashness—creative application and not brute force. Our movements and decisions define us: We must be sure to act with deliberation, boldness, and persistence. Those are the attributes of right and effective action. Nothing else—not thinking or evasion or aid from others. Action is the solution and the cure to our predicaments.”

Be deliberate and bold in your actions. If you have a problem, stop thinking about your problem and start taking action to solve it. Solutions and motivation are born in action.


“In a world where we increasingly work for ourselves, are responsible for ourselves, it makes sense to view ourselves like a start-up—a start-up of one. And that means changing the relationship with failure. It means iterating, failing, and improving. Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail.”

Treat yourself as a startup of one.

“The one way to guarantee we don’t benefit from failure—to ensure it is a bad thing—is to not learn from it. To continue to try the same thing over and over (which is the definition of insanity for a reason). People fail in small ways all the time. But they don’t learn. They don’t listen. They don’t see the problems that failure exposes. It doesn’t make them better.”

Failure is not inherently a good thing. It’s a useful tool if you’re willing to reflect on your failure and learn something from it. If you don’t do that, failure is just painful.


“Goals help put the blips and bumps in proper proportion.”

Goals provide you with a guiding light that will help you see the bigger picture when you start getting caught up in the day to day noise of life. They give you a north star to move towards.


“Adversity can harden you. Or it can loosen you up and make you better—if you let it.”

Make adversity your ally.

Break the rules

“While others obsess with observing the rules, we’re subtly undermining them and subverting them to our advantage. Think water. When dammed by a man-made obstacle, it does not simply sit stagnant. Instead, its energy is stored and deployed, fueling the power plants that run entire cities.”

Be like water. Be willing to adjust your plan. Be willing to try unconventional tactics. Be willing to do the things that other people aren’t willing to do because they’re scared.

We can’t always win

“Perceptions can be managed. Actions can be directed. We can always think clearly, respond creatively. Look for opportunity, seize the initiative. What we can’t do is control the world around us—not as much as we’d like to, anyway. We might perceive things well, then act rightly, and fail anyway.”

No matter how well you manage your perceptions or how high quality your actions are, you won’t always succeed. The world is complex and uncertain, which means that failure is inevitable.


“If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul. The will is the one thing we control completely, always. Whereas I can try to mitigate harmful perceptions and give 100 percent of my energy to actions, those attempts can be thwarted or inhibited. My will is different, because it is within me.”

Your will defines you. It gets you through the tough times and allows you to enjoy the good ones.

Life’s only guarantee

“The only guarantee, ever, is that things will go wrong. The only thing we can use to mitigate this is anticipation. Because the only variable we control completely is ourselves.”

Things will go wrong, and that’s okay. If you’re prepared for a few hiccups, you won’t be surprised or devastated when they come.


“Death doesn’t make life pointless, but rather purposeful.”

“We forget how light our grip on life really is. Otherwise, we wouldn’t spend so much time obsessing over trivialities, or trying to become famous, make more money than we could ever spend in our lifetime, or make plans far off in the future. All of these are negated by death.”

Not only does the inevitably of death make life meaningful, but it gives us an excuse to not waste time dealing with trivial things or pursuits that won’t matter when we’re on our deathbed.

“If something is in our control, it’s worth every ounce of our efforts and energy. Death is not one of those things—it is not in our control how long we will live or what will come and take us from life. But thinking about and being aware of our mortality creates real perspective and urgency. It doesn’t need to be depressing. Because it’s invigorating.”

Death doesn’t have to be a taboo subject; it can be an energizing source of gaining perspective and motivation.

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